(4S,5R)-cis-4-methyl-5-phenyl-thiazolidinethione | 1305353-00-7

• 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: (4S,5R)-cis-4-methyl-5-phenyl-thiazolidinethione
• 英文别名: (4S,5R)-4-methyl-5-phenyl-1,3-thiazolidine-2-thione
• CAS: 1305353-00-7
• 化学式: C₁₀H₁₁NS₂
• 分子量: 209.336
• InChiKey: MDBSLGONFDHHGI-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-cis-4-methyl-5-phenyl-thiazolidinethione 、 硫酸二甲酯 生成 (4S,5R)-4-methyl-2-methylsulfanyl-5-phenyl-4,5-dihydro-1,3-thiazole
  参考文献：
  名称：

  KNIEZO L.; KRISTIAN P.; BUDESINSKY M.; HAVRILOVA K., COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 3, 717-728

  摘要：

  DOI：
• 作为产物：
  描述：

  盐酸麻黄素 在 氯化亚砜 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 (4S,5R)-cis-4-methyl-5-phenyl-thiazolidinethione
  参考文献：
  名称：

  Efficient synthesis of cis-thiazolidinethiones derived from ephedrines

  摘要：

  The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 degrees C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The H-1 and C-13 NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.016

文献信息

• Efficient synthesis of cis-thiazolidinethiones derived from ephedrines
  作者：Alejandro Cruz、Itzia I. Padilla-Martínez、Efrén V. García-Báez

  DOI：10.1016/j.tetasy.2011.02.016

  日期：2011.2

  The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 degrees C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The H-1 and C-13 NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed. (C) 2011 Elsevier Ltd. All rights reserved.
• KNIEZO L.; KRISTIAN P.; BUDESINSKY M.; HAVRILOVA K., COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 3, 717-728
  作者：KNIEZO L.、 KRISTIAN P.、 BUDESINSKY M.、 HAVRILOVA K.

  DOI：——

  日期：——