(S)-3-(3',4'-dimethylbenzoyl)-N-(α-phenylethyl)propanamide | 1020690-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(3',4'-dimethylbenzoyl)-N-(α-phenylethyl)propanamide
• 英文别名: 4-(3,4-dimethylphenyl)-4-oxo-N-[(1S)-1-phenylethyl]butanamide
• CAS: 1020690-41-8
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: UVWGWNWTERZWMC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(3',4'-dimethylbenzoyl)-N-(α-phenylethyl)propanamide 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 (S)-5-(3,4-dimethylphenyl)dihydrofuran-2(3H)-one 、 (R)-γ-(3,4-dimethylphenyl)-γ-butyrolactone
  参考文献：
  名称：

  Cascade enantioselective synthesis of γ-aryl-γ-butyrolactones with a delayed stereoselective step

  摘要：

  Enantioselective synthesis of gamma-aryl-gamma-butyrolactones is achieved using (S)-1-phenylethylamine as a chiral auxiliary. The synthesis involves cascade formation-destruction-formation of the chiral centre with a delayed stereoselective step. The actual stereoselective step has been found to be intramolecular nucleophilic attack on a diastereotopic carbocation formed, thereby resulting in the formation of non-racemic gamma-aryl-gamma-butyrolactones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.077
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 5-(3,4-dimethylphenyl)furan-2-(3H)one 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到(S)-3-(3',4'-dimethylbenzoyl)-N-(α-phenylethyl)propanamide
  参考文献：
  名称：

  Cascade enantioselective synthesis of γ-aryl-γ-butyrolactones with a delayed stereoselective step

  摘要：

  Enantioselective synthesis of gamma-aryl-gamma-butyrolactones is achieved using (S)-1-phenylethylamine as a chiral auxiliary. The synthesis involves cascade formation-destruction-formation of the chiral centre with a delayed stereoselective step. The actual stereoselective step has been found to be intramolecular nucleophilic attack on a diastereotopic carbocation formed, thereby resulting in the formation of non-racemic gamma-aryl-gamma-butyrolactones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.077

文献信息

• Cascade enantioselective synthesis of γ-aryl-γ-butyrolactones with a delayed stereoselective step
  作者：Anil V. Karnik、Suchitra S. Kamath

  DOI：10.1016/j.tet.2008.01.077

  日期：2008.3

  Enantioselective synthesis of gamma-aryl-gamma-butyrolactones is achieved using (S)-1-phenylethylamine as a chiral auxiliary. The synthesis involves cascade formation-destruction-formation of the chiral centre with a delayed stereoselective step. The actual stereoselective step has been found to be intramolecular nucleophilic attack on a diastereotopic carbocation formed, thereby resulting in the formation of non-racemic gamma-aryl-gamma-butyrolactones. (C) 2008 Elsevier Ltd. All rights reserved.