(E)-N-Methoxy-N-methyl-4,6-dimethyl-5-hydroxy-2-heptenamide | 147753-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-N-Methoxy-N-methyl-4,6-dimethyl-5-hydroxy-2-heptenamide
• 英文别名: (E,4S,5S)-5-hydroxy-N-methoxy-N,4,6-trimethylhept-2-enamide
• CAS: 147753-16-0
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: KKLBZELBGRZGDT-BZGQNNPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-Methoxy-N-methyl-4,6-dimethyl-5-hydroxy-2-heptenamide 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.75h， 生成 (2R,4R,5S,6S)-4-(2-Oxopropyl)-5-methyl-6-(1-methylethyl)-2-phenyl-1,3-dioxane
  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：

  2,4-Dimethyl-3-<(tert-butyldimethylsilyl)oxy>pentanal 在 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 (E)-N-Methoxy-N-methyl-4,6-dimethyl-5-hydroxy-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.