N-[(E)-3-(4-methylphenyl)but-2-enyl]-N-[(1R)-1-phenylethyl]propanamide | 1387578-92-8

• 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: N-[(E)-3-(4-methylphenyl)but-2-enyl]-N-[(1R)-1-phenylethyl]propanamide
• CAS: 1387578-92-8
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: XMDNABBREYYVEG-LRXXLLMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[(E)-3-(4-methylphenyl)but-2-enyl]-N-[(1R)-1-phenylethyl]propanamide 在 titanium(IV) isopropylate 、 Wilkinson's catalyst 、 乙烯 、 二苯基硅烷 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 正己烷 、 氯仿 、 甲苯 为溶剂， 反应 53.5h， 生成 (3R)-2,3-dimethyl-3-p-tolylcyclopentanone
  参考文献：
  名称：

  Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone

  摘要：

  Excess lithium hexamethyldisilazide (LHMDS) with LiCl prompted the asymmetric aza-Claisen rearrangement of carboxamide and retarded the decomposition of its amide enolate. The addition of these two reagents was a key step that led to the total synthesis of (+)-alpha-cuparenone with a stereogenic quaternary center. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.016
• 作为产物：
  描述：

  、 丙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到N-[(E)-3-(4-methylphenyl)but-2-enyl]-N-[(1R)-1-phenylethyl]propanamide
  参考文献：
  名称：

  Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone

  摘要：

  Excess lithium hexamethyldisilazide (LHMDS) with LiCl prompted the asymmetric aza-Claisen rearrangement of carboxamide and retarded the decomposition of its amide enolate. The addition of these two reagents was a key step that led to the total synthesis of (+)-alpha-cuparenone with a stereogenic quaternary center. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.016

文献信息

• Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone
  作者：Takeshi Nishii、Fumiaki Miyamae、Makoto Yoshizuka、Hiroto Kaku、Mitsuyo Horikawa、Makoto Inai、Tetsuto Tsunoda

  DOI：10.1016/j.tetasy.2012.05.016

  日期：2012.5

  Excess lithium hexamethyldisilazide (LHMDS) with LiCl prompted the asymmetric aza-Claisen rearrangement of carboxamide and retarded the decomposition of its amide enolate. The addition of these two reagents was a key step that led to the total synthesis of (+)-alpha-cuparenone with a stereogenic quaternary center. (C) 2012 Elsevier Ltd. All rights reserved.