(2S,3R)-2,3-dimethyl-3-(4-methylphenyl)-N-[(1R)-1-phenylethyl]pent-4-enamide | 1387578-93-9

• 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: (2S,3R)-2,3-dimethyl-3-(4-methylphenyl)-N-[(1R)-1-phenylethyl]pent-4-enamide
• CAS: 1387578-93-9
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: KCACRZJTKPNQSX-JBYIUTFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-dimethyl-3-(4-methylphenyl)-N-[(1R)-1-phenylethyl]pent-4-enamide 在 titanium(IV) isopropylate 、 Wilkinson's catalyst 、 乙烯 、 二苯基硅烷 、 sodium hydride 作用下， 以 氯仿 、 二乙二醇二甲醚 为溶剂， 反应 47.0h， 生成 (+)-α-cuparenone
  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：

  N-[(E)-3-(4-methylphenyl)but-2-enyl]-N-[(1R)-1-phenylethyl]propanamide 在 lithium chloride 、 lithium hexamethyldisilazane 、 氯化铵 作用下， 以 正己烷 、 甲苯 、 水 为溶剂， 反应 6.5h， 生成 (2S,3R)-2,3-dimethyl-3-(4-methylphenyl)-N-[(1R)-1-phenylethyl]pent-4-enamide 、 (2R,3S)-2,3-dimethyl-3-(4-methylphenyl)-N-[(1R)-1-phenylethyl]pent-4-enamide
  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.