1-[(S)-1-phenylethyl]-trans-(2S,5S)-bis(1-hydroxy-1,1-diphenylmethyl)pyrrolidine | 446823-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(S)-1-phenylethyl]-trans-(2S,5S)-bis(1-hydroxy-1,1-diphenylmethyl)pyrrolidine
• 英文别名: [(2S,5S)-5-[hydroxy(diphenyl)methyl]-1-[(1S)-1-phenylethyl]pyrrolidin-2-yl]-diphenylmethanol
• CAS: 446823-61-6
• 化学式: C₃₈H₃₇NO₂
• 分子量: 539.717
• InChiKey: CLYXFVXKVSROQY-PGCXCKJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(S)-1-phenylethyl]-trans-(2S,5S)-bis(1-hydroxy-1,1-diphenylmethyl)pyrrolidine 在 palladium dihydroxide 氢气 、 1,8-双二甲氨基萘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 trans-(2S,5S)-bis(1-trimethylsilyloxy-1,1-diphenylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of new, highly hindered C2-symmetric trans-(2S,5S)-disubstituted pyrrolidines

  摘要：

  trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00032-0
• 作为产物：
  描述：

  二甲基2,5-二溴己二酸酯 在 cerium(III) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.5h， 生成 1-[(S)-1-phenylethyl]-trans-(2S,5S)-bis(1-hydroxy-1,1-diphenylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of new, highly hindered C2-symmetric trans-(2S,5S)-disubstituted pyrrolidines

  摘要：

  trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00032-0

文献信息

• Synthesis of new, highly hindered C2-symmetric trans-(2S,5S)-disubstituted pyrrolidines
  作者：Varinder K. Aggarwal、Franck Sandrinelli、Jonathan P.H. Charmant

  DOI：10.1016/s0957-4166(02)00032-0

  日期：2002.2

  trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.