(5S)-5-(4-methylbenzyl)pyrrolidin-2-one | 606143-40-2

• 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: (5S)-5-(4-methylbenzyl)pyrrolidin-2-one
• 英文别名: (5S)-5-[(4-methylphenyl)methyl]pyrrolidin-2-one
• CAS: 606143-40-2
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: YTDDWIMFILMJFM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S)-5-(4-methylbenzyl)pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(2S)-2-(4-methylbenzyl)pyrrolidine
  参考文献：
  名称：

  Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines

  摘要：

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00589-5
• 作为产物：
  描述：

  (2'S,5S)-2'-(methoxymethyl)-5-(4-methylbenzyl)[1,1']bipyrrolidinyl-2-one 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 以93%的产率得到(5S)-5-(4-methylbenzyl)pyrrolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines

  摘要：

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00589-5

文献信息

• Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines
  作者：Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/s0957-4166(03)00589-5

  日期：2003.9

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.