Ethyl 1-Methyl-2-(hydroxymethyl)-5-oxocyclopentane-1-carboxylate | 134906-25-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 1-Methyl-2-(hydroxymethyl)-5-oxocyclopentane-1-carboxylate
• CAS: 134906-25-5
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: RFDILHNCPHVMBU-XCBNKYQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  ethyl 2-methyl-3-oxo-hept-6-enoate 在 copper diacetate 、 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 生成 Ethyl 1-methyl-6-oxocyclohex-3-ene-1-carboxylate 、 Ethyl 1-Methyl-6-oxo-2-cyclohexenecarboxylate 、 Ethyl 1-Methyl-2-methylene-5-oxocyclopentanecarboxylate 、 Ethyl 1-Methyl-2-(hydroxymethyl)-5-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Solvent effects on manganese(III)-based oxidative free-radical cyclizations: ethanol and acetic acid

  摘要：

  Ethanol complements the typical solvent, acetic acid, for Mn(III)-based oxidative free-radical cyclizations. Cyclization of enol ether 1c to give gibberellic acid intermediate 6c is successful in ethanol, but not in acetic acid. Ethanol acts as a reducing agent for primary radicals, converting 13 and 33 to alkanes 17 and 32. Acetylenes can be used as substrates since the vinyl radicals 24 and 25 are reduced by ethanol to alkenes 26-28. The 1-hydroxyethyl radical obtained from ethanol is oxidized to acetaldehyde by Mn(III). The effect of solvent on the oxidative cyclization of unsaturated beta-keto esters 35 and 48 was examined. A higher percentage of 5-exo product is obtained in ethanol. The primary cyclopentanemethyl radicals 40 and 53 are oxidized mainly to alkenes 43 and 57 in ethanol and mainly to the alcohols 42 and 55 and lactones 41 and 58 in acetic acid.

  DOI：

  10.1021/jo00019a014