(2R,3S)-3-benzyl-1-(1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid benzyl ester | 681283-54-5

• 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)-3-benzyl-1-(1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid benzyl ester
• 英文别名: benzyl (2R,3S)-3-benzyl-1-[(1R)-1-phenylethyl]pyrrolidine-2-carboxylate
• CAS: 681283-54-5
• 化学式: C₂₇H₂₉NO₂
• 分子量: 399.533
• InChiKey: UDUHZPQFPPFPJR-LPPUWEFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-benzyl-1-(1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到(2R,3S)-3-benzyl-pyrrolidine-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  Amino-zinc-ene-enolate cyclisation: a short access to (2S,3R)- and (2S,3S)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids)

  摘要：

  The synthesis of 3-benzylprolines can be easily achieved in a diastereoselective and enantioselective way via amino-zincene-enolate cyclisation. Transmetalation of the cyclic zinc intermediate with Pd-2(dba)(3)/P(o-Tolyl)(3) allowed functionalisation with an aromatic ring. One-pot hydrogenolysis and Boc-protection led to the cis-isomer readily usable for peptide synthesis. The transisomer was obtained by epimerisation of the alpha-centre in a sealed tue Lit 200 degreesC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.039
• 作为产物：
  描述：

  碘苯 、 (R)-benzyl 2-(but-3-enyl(1-phenylethyl)amino)acetate 在 tris(dibenzylideneacetone)dipalladium (0) zinc dibromide 、 lithium diisopropyl amide 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以50%的产率得到(2R,3S)-3-benzyl-1-(1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Amino-zinc-ene-enolate cyclisation: a short access to (2S,3R)- and (2S,3S)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids)

  摘要：

  The synthesis of 3-benzylprolines can be easily achieved in a diastereoselective and enantioselective way via amino-zincene-enolate cyclisation. Transmetalation of the cyclic zinc intermediate with Pd-2(dba)(3)/P(o-Tolyl)(3) allowed functionalisation with an aromatic ring. One-pot hydrogenolysis and Boc-protection led to the cis-isomer readily usable for peptide synthesis. The transisomer was obtained by epimerisation of the alpha-centre in a sealed tue Lit 200 degreesC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.039

文献信息

• Amino-zinc-ene-enolate cyclisation: a short access to (2S,3R)- and (2S,3S)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids)
  作者：Jean Quancard、Hervé Magellan、Solange Lavielle、Gérard Chassaing、Philippe Karoyan

  DOI：10.1016/j.tetlet.2004.01.039

  日期：2004.3

  The synthesis of 3-benzylprolines can be easily achieved in a diastereoselective and enantioselective way via amino-zincene-enolate cyclisation. Transmetalation of the cyclic zinc intermediate with Pd-2(dba)(3)/P(o-Tolyl)(3) allowed functionalisation with an aromatic ring. One-pot hydrogenolysis and Boc-protection led to the cis-isomer readily usable for peptide synthesis. The transisomer was obtained by epimerisation of the alpha-centre in a sealed tue Lit 200 degreesC. (C) 2004 Elsevier Ltd. All rights reserved.