cyano-(3-methyl-cyclohex-2-enyliden)-acetic acid | 124648-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cyano-(3-methyl-cyclohex-2-enyliden)-acetic acid
• 英文别名: Cyan-(3-methyl-cyclohex-2-enyliden)-essigsaeure；2-cyano-2-(3-methylcyclohex-2-en-1-ylidene)acetic acid
• CAS: 124648-08-4
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: PAWSRKQIJGNQFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cyano-(3-methyl-cyclohex-2-enyliden)-acetic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3-甲基-2-环己烯-1-酮 、 丙二酸
  参考文献：
  名称：

  Farmer; Ross, Journal of the Chemical Society, 1926, p. 3234,3237

  摘要：

  DOI：
• 作为产物：
  描述：

  cyano-(3-methyl-cyclohex-2-enyliden)-acetic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 cyano-(3-methyl-cyclohex-2-enyliden)-acetic acid
  参考文献：
  名称：

  Assignment of stereochemistry to cyclohexenylidenecyanoacetates by1H NMR spectroscopy

  摘要：

  AbstractThe stereochemistry of various pairs of isomeric 2‐cyclohexen‐1‐ylidenecyanoacetates was assigned using 1H NMR spectroscopy. The isomers with the γ‐methylene or the γ‐vinyl protons cis to the carbalkoxy group were found to have the signals of these protons at approximately 0.3 ppm and 1 ppm, respectively, downfield relative to their geometrical isomers or the corresponding 2‐cyclohexen‐1‐ylidenemalononitriles. The observation regarding the γ‐vinyl proton proved useful for the assignment of configuration to cyclohex‐enylidenecyanoacetates derived form cholest‐4‐en‐3‐one. The large and constant downfield shift (c. 1 ppm) of the γ‐vinyl proton when cis to the ester group results from the rigid cyclohexenylidenecyanoacetate system, in which the vinylic proton can approach more closely to the magnetically anisotropic ester carbonyl group.

  DOI：

  10.1002/mrc.1270150405