10-chloro-isopulegol | 139721-76-9

• 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: 10-chloro-isopulegol
• 英文别名: 10-Chloroisopulegol；2-(3-chloroprop-1-en-2-yl)-5-methylcyclohexan-1-ol
• CAS: 139721-76-9
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: XOTRDDZNJYMXNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  251.5±28.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-chloro-isopulegol 在 sodium hydroxide 、 十六烷基三丁基溴化磷 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.08h， 生成 E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone
  参考文献：
  名称：

  In Vivo Studies on the Metabolism of the Monoterpene Pulegone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach:  Explanation for the Toxicity Differences between (S)-(−)- and (R)-(+)-Pulegone

  摘要：

  The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.

  DOI：

  10.1021/jf034702u
• 作为产物：
  描述：

  异蒲勒醇 在 磺酰氯 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到10-chloro-isopulegol
  参考文献：
  名称：

  异硫氰酸烯丙酯氯化法

  摘要：

  磺酰氯是用于对带有异丙烯基或异丙烯基部分的烯烃进行烯丙基氯化的方便试剂。取代以高收率和烯丙基重排发生，在大多数情况下产生仲氯化物。

  DOI：

  10.1016/s0040-4039(00)76192-2