N-((1S,2S)-2-hydroxy-1-methyl-2-phenylethyl)(2Z)-3-methyl-N-methylbut-2-enamide | 332842-76-9

• 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: N-((1S,2S)-2-hydroxy-1-methyl-2-phenylethyl)(2Z)-3-methyl-N-methylbut-2-enamide
• 英文别名: N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,3-dimethylbut-2-enamide
• CAS: 332842-76-9
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: VCXPASUOIMTRKV-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1S,2S)-2-hydroxy-1-methyl-2-phenylethyl)(2Z)-3-methyl-N-methylbut-2-enamide 在 正丁基锂 、 lithium amidotrihydroborate 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.17h， 生成 (S)-2-ethyl-3-methyl-3-buten-1-ol
  参考文献：
  名称：

  Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)

  摘要：

  [GRAPHICS]Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned, Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) reduction of a beta -hydroxyketone, and finally a lactone annulation reaction.

  DOI：

  10.1021/ol015531m
• 作为产物：
  描述：

  3-甲基巴豆酰氯 、 (1S,2S)-2-甲氨基-1-苯基丙-1-醇 、 三乙胺 以 四氢呋喃 为溶剂， 反应 0.33h， 以79%的产率得到N-((1S,2S)-2-hydroxy-1-methyl-2-phenylethyl)(2Z)-3-methyl-N-methylbut-2-enamide
  参考文献：
  名称：

  Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)

  摘要：

  [GRAPHICS]Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned, Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) reduction of a beta -hydroxyketone, and finally a lactone annulation reaction.

  DOI：

  10.1021/ol015531m

文献信息

• Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)
  作者：Gary E. Keck、Chad E. Knutson、Sarah A. Wiles

  DOI：10.1021/ol015531m

  日期：2001.3.1

  [GRAPHICS]Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned, Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) reduction of a beta -hydroxyketone, and finally a lactone annulation reaction.