p-menth-3-en-9-oic acid | 96562-29-7

• 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: p-menth-3-en-9-oic acid
• 英文别名: α-(4-Methyl-cyclohexen-(1)-yl-(1))-propionsaeure；p-Menth-3-en-9-saeure；1-Methyl-cyclohexen-(3)-(α-propionsaeure)-(4)；2-(4-Methylcyclohexen-1-yl)propanoic acid
• CAS: 96562-29-7
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: PACOSSZJUVEQPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-menth-3-en-9-oic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以97%的产率得到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 在 吡啶 、 氯化亚砜 、 碘 、 锌 作用下， 以 乙醚 、 苯 为溶剂， 反应 50.83h， 生成 p-menth-3-en-9-oic acid
  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

• Reaction Of β,γ-Unsaturated Carboxylic Acids With Thallium Triacetate (Tta): Lactonization<i>VS</i>Oxidative Decarboxylation
  作者：Helena M. C. Ferraz、Mčnica V. A. Grazini、Luiz F. Silva、Luiz S. Longo

  DOI：10.1080/00397919908086184

  日期：1999.6

  Abstract The reaction of six β,γ-unsaturated carboxylic acids with thallium triacetate (TTA) was studied. The nature of the products is highly sensitive to the substitution pattern of the substrates. Aliphatic acids gave mainly lactones, while those bearing an aromatic ring furnished only decarboxylation products.

  摘要 研究了六种β,γ-不饱和羧酸与三乙酸铊(TTA)的反应。产物的性质对底物的取代模式高度敏感。脂肪酸主要产生内酯，而带有芳环的脂肪酸只产生脱羧产物。
• α-Hydroxyalkyliden-lacton-umlagerung-IX
  作者：F. Korte、J. Falbe、A. Zschocke

  DOI：10.1016/0040-4020(59)80002-8

  日期：1959.1

  Generally applicable synthesises which lead to d, l-iridomyrmecin and related bicyclic γ and δ-lactones are reported.

  据报道，普遍适用的合成方法可导致d，1- iridomyrmecin以及相关的双环γ和δ-内酯。
• Harding; Haworth; Perkin, Journal of the Chemical Society, 1908, vol. 93, p. 1968
  作者：Harding、Haworth、Perkin

  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.