NP-MRD: Showing NP-Card for 10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene (NP0314117)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 12:03:17 UTC

Updated at

2022-09-11 12:03:17 UTC

NP-MRD ID

NP0314117

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene

Description

10,12-Dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]Trideca-5,9-diene belongs to the class of organic compounds known as vinyl bromides. These are vinyl halides in which a bromine atom is bonded to an sp2-hybridised carbon atom. 10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene is found in Laurencia dendroidea. 10,12-Dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]Trideca-5,9-diene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    0.4133   -2.9208   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078   -1.7449    0.0405 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2852   -0.7284   -0.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872    0.1974    0.6395 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6022   -0.2646    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6997   -0.2006    0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7928    0.0196   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444    1.7254    0.1353 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5324    1.6062    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469    2.3204   -0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5393    2.8133   -0.6403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5912    4.6059   -0.8282 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501    2.3575    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8609    0.9831    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    0.4533    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    1.4681    1.3757 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.9062   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223   -1.8122   -0.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4532   -3.4803    0.7006 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -1.1297    0.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9173    0.1528   -0.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -2.6943   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4960   -3.2194   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -3.7632   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675   -2.0997    0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709    0.0805    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -0.6219    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.8139   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4179    2.1149    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043    2.6773   -1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203    2.4529   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    2.5176    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3686    2.9947    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -1.3473    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -0.7759   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -2.0188   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -0.9991    1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  2  0
  7  8  1  0
  4  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  2  1  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  4 26  1  1
  5 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  6
 13 32  1  0
 13 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  6
 20 37  1  1
M  END


  Mrv1533004231518542D          

 21 22  0  0  0  0            999 V2000
    1.8414    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    4.5079    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.4934    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.2211    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    3.0789    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314117

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(C=C=CBr)C=CC(Cl)CC2=C(Br)CC(Br)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16Br3ClO2/c1-9-15-13(18)8-12(17)14(21-15)7-10(19)4-5-11(20-9)3-2-6-16/h3-6,9-11,13,15H,7-8H2,1H3

> <INCHI_KEY>
WWWLGURLJAZMJB-UHFFFAOYSA-N

> <FORMULA>
C15H16Br3ClO2

> <MOLECULAR_WEIGHT>
503.45

> <EXACT_MASS>
499.838896

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
38.87155690228016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene

> <ALOGPS_LOGP>
5.29

> <JCHEM_LOGP>
4.419497463333332

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144640857048968

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
99.45389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       3.437   7.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207   5.747   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.747   5.747   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.517   4.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.827   5.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.597   7.081   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0       8.827   8.415   0.000  0.00  0.00          Br+0
HETATM    9  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.517   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       6.517  -0.921   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       4.207   0.413   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       1.127   0.413   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0       1.127   5.747   0.000  0.00  0.00          Br+0
HETATM   20  C   UNK     0       3.437   4.414   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.207   3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆Br₃ClO₂

Average Mass

503.4500 Da

Monoisotopic Mass

499.83890 Da

IUPAC Name

10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene

Traditional Name

10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene

CAS Registry Number

Not Available

SMILES

CC1OC(C=C=CBr)C=CC(Cl)CC2=C(Br)CC(Br)C1O2

InChI Identifier

InChI=1S/C15H16Br3ClO2/c1-9-15-13(18)8-12(17)14(21-15)7-10(19)4-5-11(20-9)3-2-6-16/h3-6,9-11,13,15H,7-8H2,1H3

InChI Key

WWWLGURLJAZMJB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia dendroidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinyl bromides. These are vinyl halides in which a bromine atom is bonded to an sp2-hybridised carbon atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Vinyl halides

Sub Class

Vinyl bromides

Direct Parent

Vinyl bromides

Alternative Parents

Substituents

Dialkyl ether
Ether
Vinyl bromide
Organoheterocyclic compound
Haloalkene
Bromoalkene
Oxacycle
Organooxygen compound
Organochloride
Alkyl chloride
Alkyl halide
Alkyl bromide
Organobromide
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.29	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.45 m³·mol⁻¹	ChemAxon
Polarizability	38.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72746740

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene (NP0314117)

MOL for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

3D MOL for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

3D SDF for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

3D-SDF for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

PDB for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

3D PDB for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

SMILES for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

INCHI for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

Structure for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)

3D Structure for NP0314117 (10,12-dibromo-4-(3-bromopropa-1,2-dien-1-yl)-7-chloro-2-methyl-3,13-dioxabicyclo[7.3.1]trideca-5,9-diene)