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Record Information
Version2.0
Created at2024-09-11 14:22:02 UTC
Updated at2024-09-11 14:22:02 UTC
NP-MRD IDNP0338211
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-Dithiane-2,5-diol
Description1,4-Dithiane-2,5-diol belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres. 1,4-Dithiane-2,5-diol was first documented in 2013 (PMID: 24180687). Based on a literature review a significant number of articles have been published on 1,4-Dithiane-2,5-diol (PMID: 32253417) (PMID: 39240619) (PMID: 38639063) (PMID: 37272665) (PMID: 36166746) (PMID: 35548804).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC4H8O2S2
Average Mass152.2300 Da
Monoisotopic Mass151.99657 Da
IUPAC Name1,4-dithiane-2,5-diol
Traditional Name2,5-dihydroxy-1,4-dithiane
CAS Registry NumberNot Available
SMILES
OC1CSC(O)CS1
InChI Identifier
InChI=1/C4H8O2S2/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2
InChI KeyYUIOPHXTILULQC-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dithianes. These are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithianes
Sub ClassNot Available
Direct ParentDithianes
Alternative Parents
Substituents
  • 1,4-dithiane
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.38ChemAxon
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.01 m³·mol⁻¹ChemAxon
Polarizability14.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang MX, Liu J, Liu Z, Wang Y, Yang QQ, Shan W, Deng YH, Shao Z: Enantioselective synthesis of chiral alpha-alkynylated thiazolidones by tandem S-addition/acetalization of alkynyl imines. Org Biomol Chem. 2020 Apr 29;18(16):3117-3124. doi: 10.1039/d0ob00365d. [PubMed:32253417 ]
  2. Yu ZC, Zheng KL, Shen X, Zhou Y, Chen XL, Wang LS, Wu YD, Wu AX: I(2)-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode. Org Lett. 2024 Sep 20;26(37):7891-7896. doi: 10.1021/acs.orglett.4c02813. Epub 2024 Sep 6. [PubMed:39240619 ]
  3. Wei T, Xie MS, Guo HM: Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4'-thionucleosides. Chem Commun (Camb). 2024 May 7;60(38):5018-5021. doi: 10.1039/d4cc00984c. [PubMed:38639063 ]
  4. Prasad MS, Bharani S, Sivaprakash M, Vadivelu P, Kumar DSS, Chowhan LR: N-2,2,2-Trifluoroethylisatin ketimine as a 1,2-dipolarophile for [3 + 2]-addition to access optically pure spirothiazolidine oxindoles. Org Biomol Chem. 2023 Jun 21;21(24):4972-4976. doi: 10.1039/d3ob00685a. [PubMed:37272665 ]
  5. Wan X, Li H, Wang S, Wang C: Acetic Acid Mediated Regioselective [3 + 3] Cycloaddition of Substituted Cyclopropane-1,1-dicarbonitriles with 1,4-Dithiane-2,5-diol. J Org Chem. 2022 Oct 7;87(19):13375-13382. doi: 10.1021/acs.joc.2c01610. Epub 2022 Sep 27. [PubMed:36166746 ]
  6. Zhu XY, Lv MH, Zhao YN, Lan LY, Li WZ, Xiao LJ: Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter. RSC Adv. 2018 Oct 3;8(59):34000-34003. doi: 10.1039/c8ra04325f. eCollection 2018 Sep 28. [PubMed:35548804 ]
  7. Varshnaya RK, Banerjee P: Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules. Org Biomol Chem. 2017 Jun 21;15(24):5182-5190. doi: 10.1039/c7ob00941k. [PubMed:28589982 ]
  8. Duan M, Liu Y, Ao J, Xue L, Luo S, Tan Y, Qin W, Song CE, Yan H: Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes via in Situ Generated Chiral Fluoride-Catalyzed Cascade Sulfa-Michael/Aldol Reaction of 1,4-Dithiane-2,5-diol and alpha,beta-Unsaturated Ketones. Org Lett. 2017 May 5;19(9):2298-2301. doi: 10.1021/acs.orglett.7b00813. Epub 2017 Apr 25. [PubMed:28440649 ]
  9. Ciogli A, Vivek Kumar S, Mancinelli M, Mazzanti A, Perumal S, Severi C, Villani C: Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study. Org Biomol Chem. 2016 Nov 29;14(47):11137-11147. doi: 10.1039/c6ob02145j. [PubMed:27830854 ]
  10. Meninno S, Volpe C, Della Sala G, Capobianco A, Lattanzi A: Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter. Beilstein J Org Chem. 2016 Apr 5;12:643-7. doi: 10.3762/bjoc.12.63. eCollection 2016. [PubMed:27340455 ]
  11. Cheng P, Guo W, Chen P, Liu Y, Du X, Li C: The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst. Chem Commun (Camb). 2016 Feb 25;52(16):3418-21. doi: 10.1039/c5cc10292h. Epub 2016 Feb 2. [PubMed:26831820 ]
  12. Vivek Kumar S, Muthusubramanian S, Menendez JC, Perumal S: An efficient synthesis of N-substituted 3-nitrothiophen-2-amines. Beilstein J Org Chem. 2015 Sep 22;11:1707-12. doi: 10.3762/bjoc.11.185. eCollection 2015. [PubMed:26664589 ]
  13. Zaghi A, Bernardi T, Bertolasi V, Bortolini O, Massi A, De Risi C: One-Pot, Four-Step Organocatalytic Asymmetric Synthesis of Functionalized Nitrocyclopropanes. J Org Chem. 2015 Sep 18;80(18):9176-84. doi: 10.1021/acs.joc.5b01607. Epub 2015 Sep 9. [PubMed:26317611 ]
  14. Mallia CJ, Englert L, Walter GC, Baxendale IR: Thiazole formation through a modified Gewald reaction. Beilstein J Org Chem. 2015 May 26;11:875-83. doi: 10.3762/bjoc.11.98. eCollection 2015. [PubMed:26124889 ]
  15. Zheng L, Qiao Y, Lu M, Chang J: Theoretical investigations of the reaction between 1,4-dithiane-2,5-diol and azomethine imines: mechanisms and diastereoselectivity. Org Biomol Chem. 2015 Jul 21;13(27):7558-69. doi: 10.1039/c5ob00807g. [PubMed:26079432 ]
  16. Zhong Y, Ma S, Li B, Jiang X, Wang R: Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation of 1,4-Dithiane-2,5-diol with Maleimides. J Org Chem. 2015 Jul 2;80(13):6870-4. doi: 10.1021/acs.joc.5b00897. Epub 2015 Jun 11. [PubMed:26035462 ]
  17. Gui YY, Yang J, Qi LW, Wang X, Tian F, Li XN, Peng L, Wang LX: A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters. Org Biomol Chem. 2015 Jun 14;13(22):6371-9. doi: 10.1039/c5ob00774g. [PubMed:25974840 ]
  18. Sathishkannan G, Srinivasan K: [3+3] Annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes. Chem Commun (Camb). 2014 Apr 21;50(31):4062-4. doi: 10.1039/c4cc00565a. [PubMed:24608341 ]
  19. Fang X, Li J, Tao HY, Wang CJ: Highly diastereoselective DABCO-catalyzed [3 + 3]-cycloaddition of 1,4-dithiane-2,5-diol with azomethine imines. Org Lett. 2013 Nov 1;15(21):5554-7. doi: 10.1021/ol402724h. Epub 2013 Oct 24. [PubMed:24180687 ]