trans-4-methyl-5-phenyl-1,3-thiazolidine-2-thione

• 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: trans-4-methyl-5-phenyl-1,3-thiazolidine-2-thione
• 英文别名: trans-5-phenyl-4-methyl-1,3-thiazolidine-2-thione；trans-4-methyl-5-phenyl-2-thiazolidinethione；(4S,5S)-4-methyl-5-phenyl-1,3-thiazolidine-2-thione
• 化学式: C₁₀H₁₁NS₂
• 分子量: 209.336
• InChiKey: MDBSLGONFDHHGI-IONNQARKSA-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

• 作为产物：
  描述：

  2-氨基-1-苯基-1-丙醇盐酸盐 在 盐酸 、 sodium hydroxide 、 sodium hydrogensulfide 、 氯化亚砜 、 sodium carbonate 、 三氯化磷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 34.5h， 生成 trans-4-methyl-5-phenyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Kniezo, Ladislav; Kristian, Pavol; Budesinsky, Milos, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 3, p. 717 - 728

  摘要：

  DOI：

文献信息

• Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide
  作者：Jef R. Vanhoof、Robin Dirix、Dirk E. De Vos

  DOI：10.1039/d2gc03879j

  日期：——

  olefins with NH3 and CO2 or CS2 in a telescoped sequence is reported, forming 2-oxazolidinones or 2-thiazolidinethiones. The reaction proceeds via a N–H aziridine, which subsequently undergoes ring expansion with CO2 or CS2. Both steps are mediated by the same simple iodide catalyst and total yields of up to 91% referring to the alkene are achieved with excellent regioselectivities. This sustainable

  N-杂环是在有机合成和应用中经常出现的重要结构基序。因此，非常需要使用烯烃等常见起始原料的直接和绿色合成方法。在此，报道了芳香族烯烃与 NH 3和 CO 2或 CS 2以伸缩序列进行无金属电化学偶联，形成 2-恶唑烷酮或 ​​2-噻唑烷硫酮。该反应通过N-H 氮丙啶进行，随后与 CO 2或 CS 2发生扩环. 这两个步骤均由相同的简单碘化物催化剂介导，并且以出色的区域选择性实现了高达 91% 的烯烃总收率。这种使用现成材料的可持续反应具有出色的原子效率，只有 H 2作为潜在有用的副产物。
• Reactivity of .beta.-Amino Alcohols with Carbon Disulfide Study on the Synthesis of 2-Oxazolidinethiones and 2-Thiazolidinethiones
  作者：Dominique Delaunay、Loiec Toupet、Maurice Le Corre

  DOI：10.1021/jo00125a059

  日期：1995.10
• 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.