2-(1,4,4-trimethyl-cyclohex-2-enyl) acetic acid | 147397-88-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1,4,4-trimethyl-cyclohex-2-enyl) acetic acid
• 英文别名: (1,5,5-trimethyl-2-cyclohexen-1-yl)acetic acid；1,5,5-trimethyl-(2-cyclohexen-1-yl)acetic acid；1,5,5-trimethyl-2-cyclohexen-1-acetic acid；2-(1,5,5-Trimethylcyclohex-2-en-1-yl)acetic acid；2-(1,5,5-trimethylcyclohex-2-en-1-yl)acetic acid
• CAS: 147397-88-4
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: NTLGLUJPDBTZPM-UHFFFAOYSA-N

物化性质

• 沸点：
  272.7±9.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2-(1,4,4-trimethyl-cyclohex-2-enyl) acetic acid 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以69%的产率得到2-chloro-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one
  参考文献：
  名称：

  Biotransformations of bicyclic trimethylcyclohexane chloro-, bromo- and iodolactones using fungal strains

  摘要：

  Several fungal strains (Fusarium, Botrytis, Beauveria) were screened for their ability to transform three bicyclic halo-gamma-lactones with a trimethylcyclohexane ring. Most of the micro-organisms carried out hydrolytic dehalogenation and transformed these lactones into two hydroxy-gamma-lactones: cis (-)-2-hydroxy-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one and trans (+)-2-hydroxy- 4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one. The structures of all substrates and products were established on the basis of their spectral data and X-ray analysis. The method presented offers an alternative route to obtaining hydroxy-lactones with high enantiomeric excess.

  DOI：

  10.3109/10242422.2010.538688
• 作为产物：
  描述：

  3,5,5-三甲基-2-环己烯-1-醇 在 丙酸 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(1,4,4-trimethyl-cyclohex-2-enyl) acetic acid
  参考文献：
  名称：

  合成中的克莱森重排：约翰逊原酸酯方案在双环内酯途径中的加速

  摘要：

  在DMF中使用酸性催化和短暂的微波热解已经实现了对原乙酸三乙酯的Claisen原酸酯重排和许多2-cycloalken-1-ol的催化。与常规的热解方法不同，通常在不到十分钟的时间内即可获得很高产率的重排产物，而克莱森产品本身无需进一步纯化。如此获得的产物的合成效用在官能化的双环内酯的一般合成中得到证明。

  DOI：

  10.1016/s0040-4020(01)80306-9

文献信息

• A New Tin-Free Source of Amidyl Radicals
  作者：Fabien Gagosz、Cecile Moutrille、Samir Z. Zard

  DOI：10.1021/ol026221m

  日期：2002.8.1

  [reaction: see text] The readily available N-(O-ethyl thiocarbonylsulfanyl)amides are powerful amidyl radical precursors that undergo 5-exo cyclization to give pyrrolidinone derivatives via a radical-chain reaction initiated by a small amount of lauroyl peroxide.

  [反应：见正文]易于获得的N-（O-乙基硫代羰基硫烷基）酰胺是强大的a基自由基前体，它们经过5-exo环化，通过少量过氧化月桂酰引发的自由基链反应生成吡咯烷酮衍生物。
• Inversion of the Direction of Stereoinduction in the Coupling of Chiral γ,δ-Unsaturated Fischer Carbene Complexes with <i>o</i>-Ethynylbenzaldehyde
  作者：Binay K. Ghorai、Suneetha Menon、Dennis Lee Johnson、James W. Herndon

  DOI：10.1021/ol025808y

  日期：2002.6.1

  [GRAPHICS]A variety of gamma,delta-unsaturated carbene complexes that feature a stereogenic center at the beta-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.
• Lactones 30. Reaction of halolactones with trialkylphosphites
  作者：Bartłomiej Pisarski、Czesław Wawrzeńczyk

  DOI：10.1016/j.tetlet.2006.07.052

  日期：2006.9

  The reaction of halolactones with trialkylphosphites in the presence of water afforded dehalogenated lactones. (c) 2006 Elsevier Ltd. All rights reserved.
• Acceleration of the orthoester Claisen rearrangement by clay catalyzed microwave thermolysis: expeditious route to bicyclic lactones
  作者：Robert S. Huber、Graham B. Jones

  DOI：10.1021/jo00047a041

  日期：1992.10
• Grabarczyk; Szumny; Gladkowski, Polish Journal of Chemistry, 2005, vol. 79, # 11, p. 1763 - 1771
  作者：Grabarczyk、Szumny、Gladkowski、Bialonska、Ciunik、Wawrzenczyk

  DOI：——

  日期：——