1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane | 73410-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane
• 英文别名: (3,3-dimethyl-2-methylidenecyclohexyl)methanol
• CAS: 73410-07-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: ZFWWSONUQRIVKW-UHFFFAOYSA-N

物化性质

• 沸点：
  215.7±9.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 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：

  1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 "iso"-β-cyclocitral 、 3,3-Dimethyl-2-methylene-cyclohexanecarbaldehyde
  参考文献：
  名称：

  Fonctionnalisation du δ-pyronène, un nouveau synthon terpénique

  摘要：

  δ-吡喃烯，是一种从肉豆蔻烯中最近工业上可获得的萜烯。它是制备用于合成香料和视黄醇的许多中间体的优秀原材料。此外，还制备了包括环戊基的新的萜烯化合物。关键词：萜烯，吡喃烯，环戊基衍生物，香料。[期刊翻译]

  DOI：

  10.1139/v96-207
• 作为产物：
  描述：

  2-(5-iodo-2-methylpentan-2-yl)-1,3-dioxolane 在 锂硼氢 、 pig liver esterase 、 水 、 四氯化锡 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 46.08h， 生成 1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane
  参考文献：
  名称：

  Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

  摘要：

  The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.019

文献信息

• Cyclic terpenoid onium salts, their preparation and uses
  申请人：SCM Corporation

  公开号：US04179468A1

  公开（公告）日：1979-12-18

  Acyclic terpenoid onium salts are cyclized in an acidic aqueous solution at a temperature of at least about 80.degree. C.

  非环烷基类萜类离子盐在酸性水溶液中至少80℃的温度下环化。
• US4179468A
  申请人：——

  公开号：US4179468A

  公开（公告）日：1979-12-18
• Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester
  作者：Yuji Namiki、Tomohiro Fujii、Masahisa Nakada

  DOI：10.1016/j.tetasy.2014.01.019

  日期：2014.5

  The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein. (C) 2014 Elsevier Ltd. All rights reserved.
• Fonctionnalisation du δ-pyronène, un nouveau synthon terpénique
  作者：Marie Jeanne Quirin、Bernard Delmond、Martine Taran

  DOI：10.1139/v96-207

  日期：1996.10.1

  δ-Pyronene, a terpenic synthon recently made industrially available from myrcene, has been characterized. It is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes and retinoids. Furthermore, new terpenic compounds including the cyclogeranyl skeleton have been prepared. Key words: terpenes, pyronenes, cyclogeranyl derivatives, perfumes. [Journal translation]

  δ-吡喃烯，是一种从肉豆蔻烯中最近工业上可获得的萜烯。它是制备用于合成香料和视黄醇的许多中间体的优秀原材料。此外，还制备了包括环戊基的新的萜烯化合物。关键词：萜烯，吡喃烯，环戊基衍生物，香料。[期刊翻译]