4-hydroxy-p-menthan-9-oic acid ethyl ester | 31538-46-2

• 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: 4-hydroxy-p-menthan-9-oic acid ethyl ester
• 英文别名: 4-Hydroxy-p-menthan-9-saeure-aethylester；Ethyl 2-(1-hydroxy-4-methylcyclohexyl)propanoate
• CAS: 31538-46-2
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: ZXEHYATUTDUJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-p-menthan-9-oic acid ethyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 53.33h， 生成 2-(4-甲基-1-环己烯-1-基)-1-丙醇
  参考文献：
  名称：

  Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization

  摘要：

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.

  DOI：

  10.1021/jo011178m
• 作为产物：
  描述：

  4-甲基环己酮 、 2-溴丙酸乙酯 在 碘 、 锌 作用下， 以 苯 为溶剂， 反应 2.5h， 以95%的产率得到4-hydroxy-p-menthan-9-oic acid ethyl ester
  参考文献：
  名称：

  Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization

  摘要：

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.

  DOI：

  10.1021/jo011178m

文献信息

• The Isomerization of 8(9)-p-Menthene^1,2
  作者：Robert L. Frank、Robert E. Berry

  DOI：10.1021/ja01163a050

  日期：1950.7
• Wallach; Rentschler, Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 271
  作者：Wallach、Rentschler

  DOI：——

  日期：——
• Wallach; Evans, Justus Liebigs Annalen der Chemie, 1908, vol. 360, p. 52
  作者：Wallach、Evans

  DOI：——

  日期：——
• Harukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 449,452
  作者：Harukawa

  DOI：——

  日期：——
• Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization
  作者：Helena M. C. Ferraz、Luiz S. Longo、Julio Zukerman-Schpector

  DOI：10.1021/jo011178m

  日期：2002.5.1

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.