1-((S)-1-Phenyl-ethyl)-3-phenylsulfanyl-pyrrolidine-2,5-dione | 335117-39-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-((S)-1-Phenyl-ethyl)-3-phenylsulfanyl-pyrrolidine-2,5-dione
• 英文别名: 1-[(1S)-1-phenylethyl]-3-phenylsulfanylpyrrolidine-2,5-dione
• CAS: 335117-39-0
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: KIDPKLDKHVQOJP-KNVGNIICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((S)-1-Phenyl-ethyl)-3-phenylsulfanyl-pyrrolidine-2,5-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到5-Hydroxy-1-((S)-1-phenyl-ethyl)-4-phenylsulfanyl-pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization

  摘要：

  Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by pi -cationic cyclination of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02037-2
• 作为产物：
  描述：

  (Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid 在 草酰氯 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 21.0h， 生成 1-((S)-1-Phenyl-ethyl)-3-phenylsulfanyl-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization

  摘要：

  Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by pi -cationic cyclination of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02037-2

文献信息

• Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization
  作者：Abderrahim Chihab-Eddine、Adam Daı̈ch、Abderrahim Jilale、Bernard Decroix

  DOI：10.1016/s0040-4039(00)02037-2

  日期：2001.1

  Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by pi -cationic cyclination of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.