4-hydroxymethyl-4-thiomethyl-thiazolidine-2-thione | 1311029-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-hydroxymethyl-4-thiomethyl-thiazolidine-2-thione
• 英文别名: 4-(Hydroxymethyl)-4-(sulfanylmethyl)-1,3-thiazolidine-2-thione
• CAS: 1311029-71-6
• 化学式: C₅H₉NOS₃
• 分子量: 195.331
• InChiKey: CBWJRUKURJUWQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxymethyl-4-thiomethyl-thiazolidine-2-thione 、 4-氯苯甲醛 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.2h， 生成 (5RS,anti)-8-(4-chlorophenyl)-7-oxa-3,9-dithia-1-azaspiro[4.5]decane-2-thione 、 (5RS,syn)-8-(4-chlorophenyl)-7-oxa-3,9-dithia-1-azaspiro[4.5]decane-2-thione
  参考文献：
  名称：

  Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

  摘要：

  The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris center dot HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.

  DOI：

  10.1021/jo2008498
• 作为产物：
  描述：

  二硫化碳 、 三羟甲基氨基甲烷盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以45%的产率得到4,4-bis(hydroxymethyl)thiazolidine-2-thione
  参考文献：
  名称：

  Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

  摘要：

  The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris center dot HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.

  DOI：

  10.1021/jo2008498

文献信息

• Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines
  作者：Cecilia Saiz、Peter Wipf、Graciela Mahler

  DOI：10.1021/jo2008498

  日期：2011.7.15

  The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris center dot HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.