(S)-3-thia-1-azabicyclo[3.3.0]octane-2-thione | 146377-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并噻唑
• 英文名称: (S)-3-thia-1-azabicyclo[3.3.0]octane-2-thione
• 英文别名: (S)-3-thia-azabicyclo[3.3.0]octane-2-thione；(7aS)-tetrahydropyrrolo[1,2-c]thiazol-3(1H)-thione；(7aS)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole-3-thione
• CAS: 146377-03-9
• 化学式: C₆H₉NS₂
• 分子量: 159.276
• InChiKey: WDPQMHSMDSUSGJ-YFKPBYRVSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  245.0±23.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-thia-1-azabicyclo[3.3.0]octane-2-thione 在 sodium hydride 作用下， 反应 7.5h， 生成 3-dicarbomethoxymethylenepyrrolidino<1,2-c>thiazolidine
  参考文献：
  名称：

  Yadav, L D S; Sharma, Sangeeta; Vaish, Anjum, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 9, p. 604 - 605

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-tetrahydropyrrolo[1,2-c]thiazol-3(1H)-one 在 tetraphosphorus decasulfide 作用下， 生成 (S)-3-thia-1-azabicyclo[3.3.0]octane-2-thione
  参考文献：
  名称：

  Kinetic resolution of secondary alcohols using proline-derived bicyclic iminium salts

  摘要：

  DOI：

  10.1016/s0040-4039(97)00815-0

文献信息

• A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines
  作者：Ning Chen、Weiyi Jia、Jiaxi Xu

  DOI：10.1002/ejoc.200900759

  日期：2009.11

  Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. Thestereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize

  牛磺酸和结构不同的取代牛磺酸已经通过由邻氨基醇或氮丙啶和二硫化碳产生的噻唑烷-2-硫酮中间体的过氧甲酸氧化合成。讨论了反应的立体化学和机理。该方法为无盐通用路线，纯化方便，可用于合成光学活性取代牛磺酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Stereospecific Benzyne-Induced Olefination from β-Amino Alcohols and Its Application to the Total Synthesis of (−)-1-Deoxy-D-fructose
  作者：Jih Ru Hwu、Yung Chang Hsu

  DOI：10.1002/chem.201001735

  日期：2011.4.18

  'Ole in one! Treatment of β‐amino alcohols with CS2 under alkaline conditions gave 1,3‐thiazolidine‐2‐thiones, which were then treated with benzyne generated in situ. The reaction underwent an unprecedented addition–elimination process to give the desired olefins in 60–87 % yields (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene).

  “合而为一！在碱性条件下用CS 2处理β-氨基醇可得到1,3-噻唑烷-2-硫酮，然后用原位生成的苯炔进行处理。反应经历了前所未有的加成-消除过程，以60-87％的收率得到了所需的烯烃（见方案； DBU = 1,8-二氮杂双环[5.4.0]十一碳-7-烯）。
• Preparation of 1,3-Thiazolidine-2-thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate
  作者：Yong-Qing Yang、Zheng Lu、Weixiang Xiong

  DOI：10.1055/s-0037-1612124

  日期：2019.4

  A simple procedure is presented for preparing 1,3-thiazolidine-2-thiones by using potassium ethylxanthate and the corresponding β-amino alcohols as the starting materials in the presence of ethanol.

  介绍了以乙基黄原酸钾和相应的β-氨基醇为原料，在乙醇存在下制备1,3-噻唑烷-2-硫酮的简单方法。
• Synthesis and structure of highly polarised double-bond compounds derived from S-proline
  作者：R.Alan Aitken、Karamat Ali、Noemı́ de Elena、Philip Lightfoot

  DOI：10.1016/s0040-4039(00)01372-1

  日期：2000.10

  Reaction of the chiral iminium salt 3 with stabilised carbanions gives the compounds 4-9 containing a highly polarised double bond. The extent of this polarisation is determined by variable temperature H-1 NMR studies, comparison of C-13 NMR chemical shifts and an X-ray structure determination. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Aitken, R. Alan; Armstrong, David P.; Galt, Ronald H. B., Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2139 - 2145
  作者：Aitken, R. Alan、Armstrong, David P.、Galt, Ronald H. B.、Mesher, Shaun T. E.

  DOI：——

  日期：——