2,2,4-Trimethyl-cyclohexen-(3)-ol | 93225-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,4-Trimethyl-cyclohexen-(3)-ol
• 英文别名: 4,6,6-Trimethylcyclohex-3-en-1-ol
• CAS: 93225-08-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: AQVLYDKLFPFGOV-UHFFFAOYSA-N

物化性质

• 沸点：
  193.0±19.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  2,2,4-Trimethyl-cyclohexen-(3)-ol 生成 2,2,4-trimethylcyclohexan-1-one
  参考文献：
  名称：

  The Cyclization of Epoxyolefins: The Reaction of Geraniolene Monoepoxide with Boron Fluoride Etherate

  摘要：

  DOI：

  10.1021/ja00879a022
• 作为产物：
  描述：

  6-羟基-3,5,5-三甲基环己-2-烯-1-酮 在 sodium tetrahydroborate 、 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 2,2,4-Trimethyl-cyclohexen-(3)-ol
  参考文献：
  名称：

  A Concise Preparation of Yuehchukene and Its Analogues

  摘要：

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.

  DOI：

  10.3987/com-00-9008

文献信息

• The Use of Nafion®-H To Promote Epoxide Cyclizations
  作者：Stephen K. Taylor、Michael G. Dickinson、Scott A. May、Dacia A. Pickering、Paul C. Sadek

  DOI：10.1055/s-1998-4495

  日期：1998.8
• A study of epoxyolefin cyclizations catalyzed by bismuth trifluoromethanesulfonate and other metal triflates
  作者：Joshua R. Lacey、Peter W. Anzalone、Christopher M. Duncan、Matthew J. Hackert、Ram S. Mohan

  DOI：10.1016/j.tetlet.2005.10.013

  日期：2005.12

  Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products. (c) 2005 Elsevier Ltd. All rights reserved.
• Demonstration of a Common Concerted Mechanistic Pathway for the Acid-Catalyzed Cyclization of 5,6-Unsaturated Oxiranes in Chemical and Enzymatic Systems
  作者：E. J. Corey、Donnette Daley Staas

  DOI：10.1021/ja980096l

  日期：1998.4.1
• A Concise Preparation of Yuehchukene and Its Analogues
  作者：Minoru Ishikura、Katsuaki Imaizumi、Nobuya Katagiri

  DOI：10.3987/com-00-9008

  日期：——

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.
• <b>The Cyclization of Epoxyolefins: The Reaction of Geraniolene Monoepoxide with Boron Fluoride Etherate</b>
  作者：David J. Goldsmith

  DOI：10.1021/ja00879a022

  日期：1962.10