NP-MRD: Showing NP-Card for (1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one (NP0331812)

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Record Information

Version

2.0

Created at

2023-09-13 16:01:17 UTC

Updated at

2024-09-03 04:17:02 UTC

NP-MRD ID

NP0331812

Natural Product DOI

https://doi.org/10.57994/0900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one

Description

(1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]Undecane-2-one belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom. Based on a literature review very few articles have been published on (1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]Undecane-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09132316012D          

 25 26  0  0  1  0            999 V2000
   -0.3726   -1.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -1.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -2.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -0.6973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0526   -0.9795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3346   -0.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -1.1098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4418   -1.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -0.3954    0.0000 Si  0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9813   -0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3346   -1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -2.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -2.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -1.5223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9287   -2.2701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9666   -2.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.6491    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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22  2  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 19 24  2  0  0  0  0
  7 25  2  0  0  0  0
M  END


  Mrv2104 09132316012D          

 25 26  0  0  1  0            999 V2000
   -0.3726   -1.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -1.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -2.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -0.6973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0526   -0.9795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3346   -0.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -1.1098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4418   -1.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -0.3954    0.0000 Si  0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9813   -0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3346   -1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -2.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -2.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -1.5223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9287   -2.2701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9666   -2.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.6491    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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22  2  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 19 24  2  0  0  0  0
  7 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331812

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CCC(=C)[C@@H](CCC2=O)O[Si](C)(C)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H36O2Si/c1-14-9-10-16-15(13-20(16,5)6)17(21)11-12-18(14)22-23(7,8)19(2,3)4/h15-16,18H,1,9-13H2,2-8H3/t15-,16+,18+/m0/s1

> <INCHI_KEY>
MCUQTBYGRVTVNG-LZLYRXPVSA-N

> <FORMULA>
C20H36O2Si

> <MOLECULAR_WEIGHT>
336.591

> <EXACT_MASS>
336.248456934

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
39.53992977135209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,9R)-5-[(tert-butyldimethylsilyl)oxy]-10,10-dimethyl-6-methylidenebicyclo[7.2.0]undecan-2-one

> <JCHEM_LOGP>
5.457899999999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.990117957440372

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9887605146614997

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
94.08469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,9R)-5-[(tert-butyldimethylsilyl)oxy]-10,10-dimethyl-6-methylidenebicyclo[7.2.0]undecan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 13-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-23         0                                  
HETATM    1  C   UNK     0      -0.696  -2.842   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.844  -2.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.844  -4.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.844  -1.302   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.384  -1.302   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       3.832  -1.828   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       3.374  -0.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.891   0.145   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.225  -0.625   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.751  -2.072   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.291  -2.072   0.000  0.00  0.00           O+0
HETATM   12 Si   UNK     0       9.061  -0.738   0.000  0.00  0.00          Si+0
HETATM   13  C   UNK     0      10.395  -1.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.728   0.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.831   0.596   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.601   1.929   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.165  -0.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.498   1.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.225  -3.519   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.891  -4.289   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.374  -4.021   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.384  -2.842   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.734  -4.237   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       7.404  -4.509   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.604   1.212   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   22                                             
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   10   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    5   23                                             
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₆O₂Si

Average Mass

336.5910 Da

Monoisotopic Mass

336.24846 Da

IUPAC Name

(1S,5R,9R)-5-[(tert-butyldimethylsilyl)oxy]-10,10-dimethyl-6-methylidenebicyclo[7.2.0]undecan-2-one

Traditional Name

(1S,5R,9R)-5-[(tert-butyldimethylsilyl)oxy]-10,10-dimethyl-6-methylidenebicyclo[7.2.0]undecan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CCC(=C)[C@@H](CCC2=O)O[Si](C)(C)C(C)(C)C

InChI Identifier

InChI=1S/C20H36O2Si/c1-14-9-10-16-15(13-20(16,5)6)17(21)11-12-18(14)22-23(7,8)19(2,3)4/h15-16,18H,1,9-13H2,2-8H3/t15-,16+,18+/m0/s1

InChI Key

MCUQTBYGRVTVNG-LZLYRXPVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.578570142, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-14	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organosilicon compounds

Direct Parent

Trialkylheterosilanes

Alternative Parents

Substituents

Trialkylheterosilane
Silyl ether
Ketone
Organic metalloid salt
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.46	ChemAxon
pKa (Strongest Acidic)	19.99	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.08 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one (NP0331812)

MOL for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

3D MOL for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

3D SDF for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

3D-SDF for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

PDB for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

3D PDB for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

SMILES for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

INCHI for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

Structure for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)

3D Structure for NP0331812 ((1S,5R,9R)-5-((tert-Butyldimethylsilyl)oxy)-10,10-dimethyl-6-methylenebicyclo[7.2.0]undecane-2-one)