methyl 5-hydroxy-7-methyl-3-methylideneoct-6-enoate | 1149614-96-9

• 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-7-methyl-3-methylideneoct-6-enoate
• CAS: 1149614-96-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: YMLWFXSLNXDNPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 methyl 3-(bromomethyl)but-3-enoate 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以70%的产率得到methyl 5-hydroxy-7-methyl-3-methylideneoct-6-enoate
  参考文献：
  名称：

  Synthesis of methyl 3-bromomethylbut-3-enoate and its reactions with aldehydes and tributylchlorostannane in the presence of zinc

  摘要：

  Methyl 3-bromomethylbut-3-enoate smoothly reacted with prenal, beta-ionylideneacetaldehyde, benzyloxyacetaldehyde, and tributylchlorostannane in the presence of zinc and aqueous ammonium chloride in tetrahydrofuran to give the corresponding delta-hydroxy-beta-methylidenecarboxylic acid esters. In the absence of ammonium chloride, satisfactory yields of the products were obtained only in the reactions with prenal and benzyloxyacetaldehyde; these reactions involved lactonization of intermediate delta-hydroxy-beta-methylidenecarboxylic acid esters, and the double carbon-carbon bond migrated to the conjugated position with the lactone carbonyl group. The condensation of beta-ionylideneacetaldehyde with methyl 3-bromomethylbut-3-enoate was successfully used to obtain isotretinoin. Initial methyl 3-bromomethylbut-3-enoate was synthesized in a good yield from readily accessible ethyl 3,3-diethoxypropionate via cyclopropanation with ethylmagnesium bromide in the presence of titanium tetra(isopropoxide), oxidation of the acetal moiety to ester, and cleavage of the cyclopropane ring in intermediate methyl (1-methylsulfonyloxycyclopropyl)acetate.

  DOI：

  10.1134/s1070428008090029