(2S)-benzyl 2-(1-hydroxyethyl)-1-pyrrolidinecarboxylate | 221072-58-8

• 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: (2S)-benzyl 2-(1-hydroxyethyl)-1-pyrrolidinecarboxylate
• 英文别名: Benzyl (2S)-2-(1-hydroxyethyl)pyrrolidine-1-carboxylate
• CAS: 221072-58-8
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: PKSHFUMWUXREEG-YUZLPWPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-benzyl 2-(1-hydroxyethyl)-1-pyrrolidinecarboxylate 在 戴斯-马丁氧化剂 作用下， 生成 (2S)-N-Benzyloxycarbony-2-(1'-methylethenyl)pyrrolidine
  参考文献：
  名称：

  Unexpected diastereoselectivity in AD of an l-proline-derived 1,1-disubstituted alkene

  摘要：

  Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)(2)PHAL or (DHQD)(2)PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)(2)PYR or (DHQD)(2)PYR ligands leads to preferences for diols 7 or 8 respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10695-5
• 作为产物：
  描述：

  Z-L-脯氨醇 在 戴斯-马丁氧化剂 作用下， 生成 (2S)-benzyl 2-(1-hydroxyethyl)-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Unexpected diastereoselectivity in AD of an l-proline-derived 1,1-disubstituted alkene

  摘要：

  Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)(2)PHAL or (DHQD)(2)PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)(2)PYR or (DHQD)(2)PYR ligands leads to preferences for diols 7 or 8 respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10695-5

文献信息

• A Formal Synthesis of Pumiliotoxin 251D, via a Highly Diastereoselective Addition of a Titanium Homoenolate to an <scp>l</scp>-Proline Derivative
  作者：Anthony G. M. Barrett、Federica Damiani

  DOI：10.1021/jo9820972

  日期：1999.2.1
• Unexpected diastereoselectivity in AD of an l-proline-derived 1,1-disubstituted alkene
  作者：John M. Gardiner、Sarah E. Bruce

  DOI：10.1016/s0040-4039(97)10695-5

  日期：1998.2

  Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)(2)PHAL or (DHQD)(2)PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)(2)PYR or (DHQD)(2)PYR ligands leads to preferences for diols 7 or 8 respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.