2,3:6,7-Diepoxygeraniol | 137917-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2,3:6,7-Diepoxygeraniol
• 英文别名: [(2S,3S)-3-[2-(3,3-dimethyloxiran-2-yl)ethyl]-3-methyloxiran-2-yl]methanol
• CAS: 137917-59-0
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: APQNQVZOITYEGF-CFGJQEBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香叶醇 在 phosphotungstic acid 、 硫酸 、 过氧化脲素 作用下， 以 水 、 异丙醇 为溶剂， 反应 4.0h， 以25%的产率得到(2S,3S)-2,3-环氧香叶醇
  参考文献：
  名称：

  Kaur, Damandeep; Manktala; Chahal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 5, p. 598 - 602

  摘要：

  DOI：

文献信息

• Selective epoxidation of monoterpenes with methyltrioxorhenium and H2O2
  作者：Aída L.P. de Villa、Dirk E. De Vos、Consuelo C. de Montes、Pierre A. Jacobs

  DOI：10.1016/s0040-4039(98)01853-x

  日期：1998.11

  terpenes such as α-pinene with H2O2 with minimal rearrangement of the epoxide. Pyridine is also critical to suppress isomerisation of the olefin substrate (in case of nerol, geraniol). The reaction can be directed towards selective single or double epoxidation, or in one step towards the rearranged product (e.g. from linalool to the ring-closure product linalool oxide).

  在吡啶作为助催化剂的存在下，CH 3 ReO 3以最小的环氧基重排催化H 2 O 2对萜烯（如α-pine烯）的环氧化。吡啶对于抑制烯烃底物的异构化也是至关重要的（如果是神经醇，香叶醇）。该反应可以针对选择性的单或双环氧化，或在一步中针对重排的产物（例如从芳樟醇到闭环产物芳樟醇氧化物）。
• Regioselective epoxidation of allylic alcohols with monoperoxyphthalic acid in water
  作者：Francesco Fringuelli、Raimondo Germani、Ferdinando Pizzo、Fabio Santinelli、Gianfranco Savelli

  DOI：10.1021/jo00030a029

  日期：1992.2

  The epoxidation of olefinic alcohols in water only has been investigated. Simple allylic alcohols are epoxidized readily and with high yields by m-chloroperoxybenzoic acid. Polyolefinic alcohols are epoxidized regioselectively and with excellent yields by monoperoxyphthalic acid controlling the pH of the medium. The reactions have been carried out in the presence and absence of surfactants, and their role has been investigated.
• Selective epoxidation of monoterpenes with H2O2 and polymer-supported methylrheniumtrioxide systems
  作者：Raffaele Saladino、Veronica Neri、Anna Rita Pelliccia、Enrico Mincione

  DOI：10.1016/s0040-4020(03)01145-1

  日期：2003.9

  A convenient and efficient synthesis of monoterpene epoxides by application of heterogeneous poly(4-vinylpyridine)/methyl rhenium trioxide (PVP/MTO) and poly styrene/methyl rhenium trioxide (PS/MTO) systems is described. Even highly sensitive terpenic epoxides were obtained in excellent yield. Environment friendly, easily available, and low cost H2O2, was used as oxidant. Catalysts were stable systems for at least five recycling experiments. (C) 2003 Elsevier Ltd. All rights reserved.