Methyl (E)-5-Hydroxy-2-heptenoate | 147753-17-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl (E)-5-Hydroxy-2-heptenoate
• 英文别名: methyl (E)-5-hydroxyhept-2-enoate
• CAS: 147753-17-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: XXDGCXMOOOIYAU-GQCTYLIASA-N

物化性质

• 沸点：
  241.1±23.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 Methyl (E)-5-Hydroxy-2-heptenoate 在 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以79%的产率得到(2R^*,4R^*,6R^*)-4-(Carbomethoxymethyl)-6-ethyl-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：

  Methyl 2-<(dimethylphenyl)silyl>-3-butenoate 、 丙醛 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到Methyl (E)-5-Hydroxy-2-heptenoate
  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

• Fujita,T. et al., Israel Journal of Chemistry, 1974, vol. 12, # 5, p. 971 - 976
  作者：Fujita,T. et al.

  DOI：——

  日期：——
• FUJITA TSUTOMU; WATANABE SHOJI; SUGA KYOICHI; NAGASE TOMOYASU, ISR. J. CHEM. <ISJC-AT>, 1974, 12, NO 5, 971-976
  作者：FUJITA TSUTOMU、 WATANABE SHOJI、 SUGA KYOICHI、 NAGASE TOMOYASU

  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.