2-[1-Cyclohexyl-meth-(Z)-ylidene]-3-hydroxy-pent-4-enoic acid ethyl ester | 136616-89-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-[1-Cyclohexyl-meth-(Z)-ylidene]-3-hydroxy-pent-4-enoic acid ethyl ester
• 英文别名: ethyl (2Z)-2-(cyclohexylmethylidene)-3-hydroxypent-4-enoate
• CAS: 136616-89-2
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: BBXMWHZPSJAHMB-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  cyclohexyl-propynoic acid ethyl ester 、 丙烯醛 生成 2-[1-Cyclohexyl-meth-(Z)-ylidene]-3-hydroxy-pent-4-enoic acid ethyl ester 、 (E)-3-Cyclohexyl-4-hydroxy-hexa-2,5-dienoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of trisubstituted .alpha.,.beta.-unsaturated esters and amides via reactions of tantalum-alkyne complexes derived from acetylenic esters and amides with carbonyl compounds

  摘要：

  Treatment of acetylenic esters with low-valent tantalum (TaCl5 and Zn) in DME and benzene produces tantalum-alkyne complexes (not isolated), which react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z isomers of trisubstituted alpha,beta-unsaturated esters in a stereoselective manner. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds at the beta-position of the amides predominantly.

  DOI：

  10.1021/jo00021a005