(4S)-5-benzyl-5-hydroxy-1-[(4-methoxyphenyl)methyl]-4-phenylmethoxypyrrolidin-2-one | 1197026-80-4

• 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: (4S)-5-benzyl-5-hydroxy-1-[(4-methoxyphenyl)methyl]-4-phenylmethoxypyrrolidin-2-one
• CAS: 1197026-80-4
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: SWHDETOGAKYIMP-QSAPEBAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-5-benzyl-5-hydroxy-1-[(4-methoxyphenyl)methyl]-4-phenylmethoxypyrrolidin-2-one 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(S,E)-5-benzylidene-4-(benzyloxy)-1-(4-methoxybenzyl)-2-pyrrolidinone
  参考文献：
  名称：

  A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine

  摘要：

  A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we have described previously. The method was applied to the asymmetric synthesis of streptopyrrolidine 5, a natural product, which exhibited significant anti-angiogenesis activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.018
• 作为产物：
  描述：

  (S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 生成 (4S)-5-benzyl-5-hydroxy-1-[(4-methoxyphenyl)methyl]-4-phenylmethoxypyrrolidin-2-one
  参考文献：
  名称：

  A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine

  摘要：

  A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we have described previously. The method was applied to the asymmetric synthesis of streptopyrrolidine 5, a natural product, which exhibited significant anti-angiogenesis activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.018

文献信息

• A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine
  作者：Shao-Hua Xiang、Hong-Qiu Yuan、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2009.08.018

  日期：2009.9

  A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we have described previously. The method was applied to the asymmetric synthesis of streptopyrrolidine 5, a natural product, which exhibited significant anti-angiogenesis activity. (C) 2009 Elsevier Ltd. All rights reserved.