(E)-N-Methoxy-N-methyl-5-(triethylsiloxy)-6-methyl-2-heptenamide | 147753-26-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-N-Methoxy-N-methyl-5-(triethylsiloxy)-6-methyl-2-heptenamide
• 英文别名: (E)-N-methoxy-N,6-dimethyl-5-triethylsilyloxyhept-2-enamide
• CAS: 147753-26-2
• 化学式: C₁₆H₃₃NO₃Si
• 分子量: 315.528
• InChiKey: QYYUEPQUIRMQSZ-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-Methoxy-N-methyl-5-(triethylsiloxy)-6-methyl-2-heptenamide 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以98%的产率得到(E)-N-Methoxy-N-methyl-5-hydroxy-6-methyl-2-heptenamide
  参考文献：
  名称：

  Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles

  摘要：

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.

  DOI：

  10.1021/jo00061a018
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 在 2,6-二甲基吡啶 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 27.5h， 生成 (E)-N-Methoxy-N-methyl-5-(triethylsiloxy)-6-methyl-2-heptenamide
  参考文献：
  名称：

  Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles

  摘要：

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.

  DOI：

  10.1021/jo00061a018

文献信息

• Evans David A., Gauchet-Prunet Joelle A., J. Org. Chem., 58 (1993) N 9, S 2446-2453
  作者：Evans David A., Gauchet-Prunet Joelle A.

  DOI：——

  日期：——
• Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles
  作者：David A. Evans、Joelle A. Gauchet-Prunet

  DOI：10.1021/jo00061a018

  日期：1993.4

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.