(4S,5S)-5-benzyl-4-(benzyloxy)-1-(4-methoxybenzyl)-2-pyrrolidinone | 1197026-72-4

• 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,5S)-5-benzyl-4-(benzyloxy)-1-(4-methoxybenzyl)-2-pyrrolidinone
• 英文别名: (4S,5S)-5-benzyl-1-[(4-methoxyphenyl)methyl]-4-phenylmethoxypyrrolidin-2-one
• CAS: 1197026-72-4
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: JWKIDTNCUIZXGC-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-benzyl-4-(benzyloxy)-1-(4-methoxybenzyl)-2-pyrrolidinone 在 三氟甲磺酸酐 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到(2S,3S)-2-benzyl-3-(benzyloxy)-1-(4-methoxybenzyl)pyrrolidine
  参考文献：
  名称：

  Amide Activation by Tf2O: Reduction of Amides to Amines by NaBH4 under Mild Conditions

  摘要：

  报道了一种快速且实用的酰胺还原为胺的方法。该方法包括使用Tf2O对酰胺进行活化，然后在室温下用四氢呋喃中的硼氢化钠进行还原。各种酰胺/内酰胺都能以良好到优异的产率生成相应的胺，即使是对立体的酰胺和二级酰胺也如此。该方法还具有其他优点，如对TBDPS基团的耐受性、反应时间短、操作简便以及纯化过程简单。

  DOI：

  10.1055/s-0030-1258111
• 作为产物：
  描述：

  (S,E)-5-benzylidene-4-(benzyloxy)-1-(4-methoxybenzyl)-2-pyrrolidinone 在 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以96%的产率得到(4S,5S)-5-benzyl-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

文献信息

• Versatile One-Pot Reductive Alkylation of Lactams/Amides via Amide Activation: Application to the Concise Syntheses of Bioactive Alkaloids (±)-Bgugaine, (±)-Coniine, (+)-Preussin, and (−)-Cassine
  作者：Kai-Jiong Xiao、Yu Wang、Ke-Yin Ye、Pei-Qiang Huang

  DOI：10.1002/chem.201002054

  日期：2010.11.15

  Direct entry: One‐pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α‐alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)‐bgugaine, (±)‐coniine, (+)‐preussin, and (−)‐cassine.

  直接输入：内酰胺的一锅法还原性烷基化/与格氏试剂的酰胺已经通过内酰胺/酰胺活化与TF实现2 O.这种方法将打开一个直接进入α -烷基化的胺。该方法的多功能性由生物活性生物碱（±）-古吉茄碱，（±）-芥子碱，（+）-普鲁素和（-）-酪氨酸的简明合成说明。
• Amide Activation by Tf2O: Reduction of Amides to Amines by NaBH4 under Mild Conditions
  作者：Pei-Qiang Huang、Shao-Hua Xiang、Jian Xu、Hong-Qiu Yuan

  DOI：10.1055/s-0030-1258111

  日期：2010.7

  An expeditious and practical method for the reduction of amides to amines is reported. The method is consisted of activation of amides with Tf2O followed by reduction with sodium borohydride in THF at room temperature. Various amides/lactams gave the corresponding amines in good to excellent yields, even with hindered amides and secondary amides. This method also presents other advantages such as TBDPS-group tolerance, short reaction time, simple workup and purification procedure.

  报道了一种快速且实用的酰胺还原为胺的方法。该方法包括使用Tf2O对酰胺进行活化，然后在室温下用四氢呋喃中的硼氢化钠进行还原。各种酰胺/内酰胺都能以良好到优异的产率生成相应的胺，即使是对立体的酰胺和二级酰胺也如此。该方法还具有其他优点，如对TBDPS基团的耐受性、反应时间短、操作简便以及纯化过程简单。
• 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.