methyl 5-hydroxy-6-methyl-2-heptenoate | 92186-76-0

• 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 5-hydroxy-6-methyl-2-heptenoate
• 英文别名: Methyl (E)-5-Hydroxy-6-methyl-2-heptenoate；(E)-ethyl 5-hydroxy-2-methyl-7-phenylhept-2-enoate；methyl (E)-5-hydroxy-6-methylhept-2-enoate
• CAS: 92186-76-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: SYNUWOANCNCLLY-GQCTYLIASA-N

物化性质

• 沸点：
  252.5±23.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  methyl 5-hydroxy-6-methyl-2-heptenoate 、 苯甲醛 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以71%的产率得到(2S^*,4R^*,6S^*)-4-(Carbomethoxymethyl)-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：

  Methyl 2-<(dimethylphenyl)silyl>-3-butenoate 、 异丁醛 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到methyl 5-hydroxy-6-methyl-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

• Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction
  作者：Liliana Becerra-Figueroa、Elodie Brun、Michael Mathieson、Louis J. Farrugia、Claire Wilson、Joëlle Prunet、Diego Gamba-Sánchez

  DOI：10.1039/c6ob02333a

  日期：——

  A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yields.

  描述了三氟甲基化的1，3-二恶烷的高度非对映选择性的合成。该反应以加成/氧杂-迈克尔序列进行，并且在温和的反应条件下有效地进行，具有良好的底物范围和可接受的良好收率。
• Condensation of crotonic and tiglic acid dianions with aldehydes and ketones
  作者：Paul R. Johnson、James D. White

  DOI：10.1021/jo00197a019

  日期：1984.11
• JOHNSON, P. R.;WHITE, J. D., J. ORG. CHEM., 1984, 49, N 23, 4424-4429
  作者：JOHNSON, P. R.、WHITE, J. D.

  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.