4-cyano-3,4-diphenylpentanoic acid dimethylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-cyano-3,4-diphenylpentanoic acid dimethylamide
• 英文别名: (3S,4S)-4-cyano-N,N-dimethyl-3,4-diphenylpentanamide
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: FZMGKOXNNNVNGR-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-cyano-3,4-diphenylpentanoic acid dimethylamide 在 硫酸 作用下， 反应 96.0h， 以78%的产率得到2,3-diphenyl-2-methylpentandioic acid 1-amide-5-dimethylamide
  参考文献：
  名称：

  Diastereoselectivity of tandem Michael addition–alkylation reactions: a convenient method for one-pot synthesis of α-branched 2,3-diphenylglutaric acid derivatives

  摘要：

  alpha-Branched 2,3-diphenylglutaric acid derivatives with two adjacent chiral centres are easily obtained by one-pot Michael addition - alkylation sequences. The diastereoselectivity observed, which varies from outstanding to moderate and even low, was found to depend on the type of the metal intermediate (nitrile vs amide) and its gamma-substitution pattern. A rigidly chelated transition state model that correctly predicts the sense of the asymmetric induction is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00298-3
• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 碘甲烷 、 α-苯基肉桂腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 以75%的产率得到4-cyano-3,4-diphenylpentanoic acid dimethylamide
  参考文献：
  名称：

  Diastereoselectivity of tandem Michael addition–alkylation reactions: a convenient method for one-pot synthesis of α-branched 2,3-diphenylglutaric acid derivatives

  摘要：

  alpha-Branched 2,3-diphenylglutaric acid derivatives with two adjacent chiral centres are easily obtained by one-pot Michael addition - alkylation sequences. The diastereoselectivity observed, which varies from outstanding to moderate and even low, was found to depend on the type of the metal intermediate (nitrile vs amide) and its gamma-substitution pattern. A rigidly chelated transition state model that correctly predicts the sense of the asymmetric induction is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00298-3

文献信息

• Diastereoselectivity of tandem Michael addition–alkylation reactions: a convenient method for one-pot synthesis of α-branched 2,3-diphenylglutaric acid derivatives
  作者：L Viteva、Tz Gospodova、Y Stefanovsky、S Angelova、L Gorrichon

  DOI：10.1016/s0040-4020(02)00298-3

  日期：2002.4

  alpha-Branched 2,3-diphenylglutaric acid derivatives with two adjacent chiral centres are easily obtained by one-pot Michael addition - alkylation sequences. The diastereoselectivity observed, which varies from outstanding to moderate and even low, was found to depend on the type of the metal intermediate (nitrile vs amide) and its gamma-substitution pattern. A rigidly chelated transition state model that correctly predicts the sense of the asymmetric induction is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.