N-((1S,2S)-1-(allyloxy)-1-phenylpropan-2-yl)-N-methylhex-5-ynamide

• 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-((1S,2S)-1-(allyloxy)-1-phenylpropan-2-yl)-N-methylhex-5-ynamide
• 英文别名: N-methyl-N-[(1S,2S)-1-phenyl-1-prop-2-enoxypropan-2-yl]hex-5-ynamide
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: RTGRXIABQGUQQE-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1S,2S)-1-(allyloxy)-1-phenylpropan-2-yl)-N-methylhex-5-ynamide 在 sodium tetrahydroborate 、 2-氟吡啶 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (2S)-2-prop-2-enylhex-5-yn-1-ol
  参考文献：
  名称：

  Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation

  摘要：

  A one-pot protocol for the asymmetric alpha-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched alpha-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

  DOI：

  10.1021/ja408856p
• 作为产物：
  描述：

  (1S,2S)-2-甲氨基-1-苯基丙-1-醇 在 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((1S,2S)-1-(allyloxy)-1-phenylpropan-2-yl)-N-methylhex-5-ynamide
  参考文献：
  名称：

  Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation

  摘要：

  A one-pot protocol for the asymmetric alpha-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched alpha-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

  DOI：

  10.1021/ja408856p

文献信息

• Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation
  作者：Bo Peng、Danny Geerdink、Nuno Maulide

  DOI：10.1021/ja408856p

  日期：2013.10.9

  A one-pot protocol for the asymmetric alpha-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched alpha-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.