(3aS)-cis-Tetrahydrothieno<2,3-d>-1,3-dithiole-2-thione | 142438-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: (3aS)-cis-Tetrahydrothieno<2,3-d>-1,3-dithiole-2-thione
• 英文别名: (3aS)-cis-Tetrahydrothieno[2,3-d]-1,3-dithiole-2-thione；(3aS,6aS)-3a,5,6,6a-tetrahydrothieno[2,3-d][1,3]dithiole-2-thione
• CAS: 142438-88-8
• 化学式: C₅H₆S₄
• 分子量: 194.367
• InChiKey: BWTJKXSNSXBREB-IMJSIDKUSA-N

物化性质

• 沸点：
  417.3±38.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3(S)-<thio>thiolane 1(R)-oxide sodium salt 在 2-chloroallyl oxalochloride 、 N,N-二异丙基乙胺 作用下， 以 二硫化碳 、 二氯甲烷 、 异丙醇 为溶剂， 反应 1.25h， 生成 (3aS)-cis-Tetrahydrothieno<2,3-d>-1,3-dithiole-2-thione
  参考文献：
  名称：

  2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R,6S)-6-(1(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem antibacterial

  摘要：

  A practical synthesis of potent penem antibacterials, CP-70,429 (1) (sulopenem) and CP-81,054 (2), is described. (L)-Aspartic acid was utilized to generate both the (3S)- and (3R)-thiolanylthio side chains of (5R,6S)-6-(1-(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem-3-carboxylic acids 1 and 2. This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19. To accommodate the fragile side chain sulfoxide moiety of the targeted beta-lactams, standard penem synthetic methodology was modified to facilitate the conversion of 15 and 19 to 1 and 2. The reactive chloroazetidinone 4b was utilized to generate key azetidinone trithiocarbonate intermediate 22 which contains the requisite penem side chain. A chemoselective oxalofluoride-based azetidinone N-acylation procedure, which avoids sulfoxide O-acylation, was required for the conversion of 22 to the penem framework.

  DOI：

  10.1021/jo00042a010