(4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione | 908343-65-7

• 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-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione
• 英文别名: (4S,5R)-cis-3,4-dimethyl-5-phenyl-thiazolidinethione；(4S,5R)-3,4-dimethyl-5-phenyl-1,3-thiazolidine-2-thione
• CAS: 908343-65-7
• 化学式: C₁₁H₁₃NS₂
• 分子量: 223.363
• InChiKey: UATVPLWAYYPNCO-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2S)-N-methylthiolephedirine
  参考文献：
  名称：

  Poelert, Martin A.; Hof, Robert P.; Peper, Nathalie C. M. W., Heterocycles, 1994, vol. 37, # 1, p. 461 - 476

  摘要：

  DOI：
• 作为产物：
  描述：

  麻黄碱 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione
  参考文献：
  名称：

  Poelert, Martin A.; Hof, Robert P.; Peper, Nathalie C. M. W., Heterocycles, 1994, vol. 37, # 1, p. 461 - 476

  摘要：

  DOI：

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.
• 1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines
  作者：Alejandro Cruz、Rosalinda Contreras、Itzia I. Padilla-Martínez、Minerva Juárez-Juárez

  DOI：10.1016/j.tetasy.2006.05.009

  日期：2006.6

  Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 degrees C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochernistry of the compounds were determined by H-1, C-13 NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis- 1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis- 1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction. (c) 2006 Elsevier Ltd. All rights reserved.
• Poelert, Martin A.; Hof, Robert P.; Peper, Nathalie C. M. W., Heterocycles, 1994, vol. 37, # 1, p. 461 - 476
  作者：Poelert, Martin A.、Hof, Robert P.、Peper, Nathalie C. M. W.、Kellogg, Richard M.

  DOI：——

  日期：——