Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 14:22:02 UTC |
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Updated at | 2024-09-11 14:22:02 UTC |
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NP-MRD ID | NP0338211 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 1,4-Dithiane-2,5-diol |
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Description | 1,4-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). |
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Structure | InChI=1/C4H8O2S2/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2 |
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Synonyms | Not Available |
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Chemical Formula | C4H8O2S2 |
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Average Mass | 152.2300 Da |
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Monoisotopic Mass | 151.99657 Da |
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IUPAC Name | 1,4-dithiane-2,5-diol |
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Traditional Name | 2,5-dihydroxy-1,4-dithiane |
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CAS Registry Number | Not Available |
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SMILES | OC1CSC(O)CS1 |
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InChI Identifier | InChI=1/C4H8O2S2/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2 |
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InChI Key | YUIOPHXTILULQC-UHFFFAOYNA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | This 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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Dithianes |
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Sub Class | Not Available |
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Direct Parent | Dithianes |
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Alternative Parents | |
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Substituents | - 1,4-dithiane
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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