(S)-2,2-dimethyl-N-[2'-(1''-phenylbut-3''-enyl)phenyl]-propionamide | 797760-23-7

• 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: (S)-2,2-dimethyl-N-[2'-(1''-phenylbut-3''-enyl)phenyl]-propionamide
• 英文别名: 2'-(1-phenyl-but-3-enyl)-2,2-dimethylpropioanilide；2,2-Dimethyl-N-{2-[(1S)-1-phenylbut-3-en-1-yl]phenyl}propanamide；2,2-dimethyl-N-[2-[(1S)-1-phenylbut-3-enyl]phenyl]propanamide
• CAS: 797760-23-7
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: WHQMRDDSNHBGPJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苄基-2,2-二甲基丙酰苯胺 、 3-溴丙烯 在 仲丁基锂 、 鹰爪豆碱 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (R)-2,2-dimethyl-N-[2'-(1''-phenylbut-3''-enyl)phenyl]-propionamide 、 (S)-2,2-dimethyl-N-[2'-(1''-phenylbut-3''-enyl)phenyl]-propionamide
  参考文献：
  名称：

  Asymmetric alkylation of N-pivaloyl-o-benzylaniline

  摘要：

  Alkylation of 2-methoxyethoxyphenyl phenylmethane using see-BuLi and (-)-sparteine has been carried out in excellent yields and up to 76% ee. The use of O'Brien's (+)-sparteine surrogate gave the opposite sense of asymmetric induction a 80% ee while the use of chiral lithium amide bases gave modest yields and ees. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.020

文献信息

• Dynamic Thermodynamic Resolution:  Solvent Effects, Mechanism, and an Asymmetric 3,4,5-Substituted Benzazepine Synthesis
  作者：Yong Sun Park、Eul Kgun Yum、Amit Basu、Peter Beak

  DOI：10.1021/ol0604015

  日期：2006.6.1

  The resolution in the lithiation-substitution sequence from 1 to 4-11 in MTBE is shown to be under thermodynamic control in contrast to the previous report of kinetic control in diethyl ether. Diastereomeric equilibration of a soluble complex is shown to be controlling and an asymmetric synthesis of a 3,4,5-substituted benzazepine is reported.
• Asymmetric alkylation of N-pivaloyl-o-benzylaniline
  作者：James A. Wilkinson、Steven B. Rossington、Sylvie Ducki、John Leonard、Nigel Hussain

  DOI：10.1016/j.tetasy.2004.08.020

  日期：2004.10

  Alkylation of 2-methoxyethoxyphenyl phenylmethane using see-BuLi and (-)-sparteine has been carried out in excellent yields and up to 76% ee. The use of O'Brien's (+)-sparteine surrogate gave the opposite sense of asymmetric induction a 80% ee while the use of chiral lithium amide bases gave modest yields and ees. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric alkylation of diarylmethane derivatives
  作者：James A. Wilkinson、Steven B. Rossington、Sylvie Ducki、John Leonard、Nigel Hussain

  DOI：10.1016/j.tet.2005.11.044

  日期：2006.2

  Deprotonation-alkylation of prochiral diarylinethane substrates using sec-BuLi and (-)-sparteine has been carried Out in excellent yields and Lip to 94% ee. A variety of enantioselective alkylations, silylations and stannylations have been performed on four different diarylmethanes. Surrogates for (+)-sparteine have also been applied in this Study including a novel surrogate. (c) 2005 Elsevier Ltd. All rights reserved.