(R)-3-phenyl-N-benzylpyrrolidine | 59349-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-3-phenyl-N-benzylpyrrolidine
• 英文别名: (S)-N-benzyl-3-phenylpyrrolidine；(S)-1-benzyl-3-phenylpyrrolidine；(3S)-1-Benzyl-3-phenylpyrrolidine
• CAS: 59349-74-5
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: XGEZXIRZOJOBFI-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-3-phenyl-N-benzylpyrrolidine 在 重铬酸吡啶 氢气 作用下， 以 甲醇 为溶剂， 生成 (3S)-3-苯基吡咯烷
  参考文献：
  名称：

  Conformationally constrained amino acids. Synthesis and optical resolution of 3-substituted proline derivatives

  摘要：

  DOI：

  10.1021/jo00288a045
• 作为产物：
  描述：

  (S)-di-tert-butyl-2-phenylsuccinate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 (R)-3-phenyl-N-benzylpyrrolidine
  参考文献：
  名称：

  Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes

  摘要：

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.

  DOI：

  10.1021/ol300980k

文献信息

• Negron, Guillermo; Roussi, Georges; Zhang, Jidong, Heterocycles, 1992, vol. 34, # 2, p. 293 - 301
  作者：Negron, Guillermo、Roussi, Georges、Zhang, Jidong

  DOI：——

  日期：——
• SUBSTITUTED NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVES, PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME AND APPLICATIONS OF ANTITUMOR THEREOF
  申请人：Zhejiang University

  公开号：EP3124486B1

  公开（公告）日：2020-12-09
• Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes
  作者：Yu-Chiang, Chung、Damodar Janmanchi、Hsyueh-Liang Wu

  DOI：10.1021/ol300980k

  日期：2012.6.1

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.
• Conformationally constrained amino acids. Synthesis and optical resolution of 3-substituted proline derivatives
  作者：John Y. L. Chung、James T. Wasicak、William A. Arnold、Catherine S. May、Alex M. Nadzan、Mark W. Holladay

  DOI：10.1021/jo00288a045

  日期：1990.1