(2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid | 1000870-85-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid
• 英文别名: (2R,3S)-1-acetyl-3-phenylpyrrolidine-2-carboxylic acid
• CAS: 1000870-85-8
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: PTZHHHNZUQJBRX-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 生成 反式-3-苯基-D-脯氨酸
  参考文献：
  名称：

  Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis: a highly enantioselective route to 3-substituted proline derivatives

  摘要：

  The highly enantioselective organocatalytic tandem reaction between 2-acylaminomalonates and alpha,beta-unsaturated aldehydes is presented. The reaction is a direct entry to 5-hydroxypyrrolidines and 3-substituted proline derivatives, which are furnished in high yields and 90-99% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.028
• 作为产物：
  描述：

  trans-N-acetyl-3-phenylproline ethyl ester 在 三氟乙酸乙酯 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis: a highly enantioselective route to 3-substituted proline derivatives

  摘要：

  The highly enantioselective organocatalytic tandem reaction between 2-acylaminomalonates and alpha,beta-unsaturated aldehydes is presented. The reaction is a direct entry to 5-hydroxypyrrolidines and 3-substituted proline derivatives, which are furnished in high yields and 90-99% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.028

文献信息

• 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
• CHUNG, JOHN Y. L.;WASICAK, JAMES T.;ARNOLD, WILLIAM A.;MAY, CATHERINE S.;+, J. ORG. CHEM., 55,(1990) N, C. 270-275
  作者：CHUNG, JOHN Y. L.、WASICAK, JAMES T.、ARNOLD, WILLIAM A.、MAY, CATHERINE S.、+

  DOI：——

  日期：——