cis-3-(ethoxycarbonyl)-5-methyl-4-hexanolide | 124732-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-3-(ethoxycarbonyl)-5-methyl-4-hexanolide
• CAS: 124732-64-5；124732-65-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: POZQREOPPJHSOP-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 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：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  Ethyl 2,2-dimethoxycyclopropane-1-carboxylate 、 异丁醛 在 氯化锆(IV) 、 对甲苯磺酸 作用下， 生成 trans-3-(ethoxycarbonyl)-5-methyl-4-hexanolide 、 cis-3-(ethoxycarbonyl)-5-methyl-4-hexanolide
  参考文献：
  名称：

  Diastereoselective ring-opening aldol-type reaction of 2,2-dialkoxycyclopropanecarboxylic esters with carbonyl compounds. 1. Synthesis of cis 3,4-substituted .gamma.-lactones

  摘要：

  The Lewis acid-promoted reactions of 2,2-dialkoxycyclopropanecarboxylic esters 4a-c with aldehydes and unsymmetrical ketones to give gamma-lactones were investigated. TiBr, is an excellent catalyst and gives cis 3,4-substituted gamma-lactones in good yields with high diastereoselectivity. SnBr4 promotes the reaction of 4a-c with aldehydes with high cis-selectivity, but does not promote the reaction of 4a with unsymmetrical ketones. ZrCl4 is moderately trans-selective in the reaction of 4a with aldehydes, while being moderately cis-selective in the reaction of 4a with unsymmetrical ketones. Cis-gamma-lactones can be converted into their trans-isomers by treatment with NaOEt in EtOH.

  DOI：

  10.1021/jo00052a028