(2S,3R)-3-(溴甲基)-2-甲基-2-(4-甲基戊-3-烯-1-基)环氧乙烷 | 73719-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (2S,3R)-3-(溴甲基)-2-甲基-2-(4-甲基戊-3-烯-1-基)环氧乙烷
• 英文名称: epoxyneryl bromide
• 英文别名: (2S-cis)-3-(Bromomethyl)-2-methyl-2-(4-methyl-3-pentenyl)oxirane；(2S,3S)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-enyl)oxirane
• CAS: 73719-17-2；91423-24-4；104372-30-7；126874-42-8
• 化学式: C₁₀H₁₇BrO
• 分子量: 233.148
• InChiKey: YBLCNHAYWVYVPC-ZJUUUORDSA-N

物化性质

• 沸点：
  249.9±15.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(溴甲基)-2-甲基-2-(4-甲基戊-3-烯-1-基)环氧乙烷 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 0.08h， 生成 tetraethyl (Z)-(2-(1-(3,7-dimethylocta-2,6-dien-1-yl)-1H-1,2,3-triazol-4-yl)ethane-1,1-diyl)bis(phosphonate)
  参考文献：
  名称：

  Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  When inhibitors of enzymes that utilize isoprenoid pyrophosphates are based on the natural substrates, a significant challenge can be to achieve selective inhibition of a specific enzyme. One element in the design process is the stereochemistry of the isoprenoid olefins. We recently reported preparation of a series of isoprenoid triazoles as potential inhibitors of geranylgeranyl transferase II but these compounds were obtained as a mixture of olefin isomers. We now have accomplished the stereoselective synthesis of these triazoles through the use of epoxy azides for the cycloaddition reaction followed by regeneration of the desired olefin. Both geranyl and neryl derivatives have been prepared as single olefin isomers through parallel reaction sequences. The products were assayed against multiple enzymes as well as in cell culture studies and surprisingly a Z-olefin isomer was found to be a potent and selective inhibitor of geranylgeranyl diphosphate synthase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.014
• 作为产物：
  描述：

  橙花醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 31.66h， 生成 (2S,3R)-3-(溴甲基)-2-甲基-2-(4-甲基戊-3-烯-1-基)环氧乙烷
  参考文献：
  名称：

  不饱和环氧化物的自由基环化

  摘要：

  由7-溴5,6-环氧庚烯衍生物（例如环氧香叶基溴化物（7））衍生的esr光谱表明，主要的自由基中间体为四氢呋喃基甲基（11），由环氧化物开环并随后将不饱和烷氧基外环化而成部首。7-氧杂双环[2.2.1]庚基甲基（12）也通过双环化形成。从（7）与氢化三正丁基锡的反应中分离出衍生自这两种中间体的产物。

  DOI：

  10.1016/s0040-4020(01)89499-0

文献信息

• [EN] HYPERFORIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF<br/>[FR] ANALOGUES DE L'HYPERFORINE, LEURS MÉTHODES DE SYNTHÈSE ET LEURS UTILISATIONS
  申请人：HARVARD COLLEGE

  公开号：WO2012167021A3

  公开（公告）日：2013-04-25
• Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase
  作者：Xiang Zhou、Sarah D. Ferree、Veronica S. Wills、Ella J. Born、Huaxiang Tong、David F. Wiemer、Sarah A. Holstein

  DOI：10.1016/j.bmc.2014.03.014

  日期：2014.5

  When inhibitors of enzymes that utilize isoprenoid pyrophosphates are based on the natural substrates, a significant challenge can be to achieve selective inhibition of a specific enzyme. One element in the design process is the stereochemistry of the isoprenoid olefins. We recently reported preparation of a series of isoprenoid triazoles as potential inhibitors of geranylgeranyl transferase II but these compounds were obtained as a mixture of olefin isomers. We now have accomplished the stereoselective synthesis of these triazoles through the use of epoxy azides for the cycloaddition reaction followed by regeneration of the desired olefin. Both geranyl and neryl derivatives have been prepared as single olefin isomers through parallel reaction sequences. The products were assayed against multiple enzymes as well as in cell culture studies and surprisingly a Z-olefin isomer was found to be a potent and selective inhibitor of geranylgeranyl diphosphate synthase. (C) 2014 Elsevier Ltd. All rights reserved.
• Free radical cyclisation of unsaturated epoxides
  作者：Rosslyn C. Gash、Finlay MacCorquodale、John C. Walton

  DOI：10.1016/s0040-4020(01)89499-0

  日期：1989.1

  The e.s.r. spectra derived from 7-bromo-5,6-epoxyheptene derivatives such as epoxygeranyl bromide (7) showed that the main free radical intermediates were tetrahydrofuranylmethyl radicals (11), formed by ring opening of the epoxide and subsequent exocyclisation of the unsaturated alkoxyl radicals. The 7-oxabicyclo[2.2.1]heptanyl methyl radicals (12) were also formed via a double cyclisation. Products

  由7-溴5,6-环氧庚烯衍生物（例如环氧香叶基溴化物（7））衍生的esr光谱表明，主要的自由基中间体为四氢呋喃基甲基（11），由环氧化物开环并随后将不饱和烷氧基外环化而成部首。7-氧杂双环[2.2.1]庚基甲基（12）也通过双环化形成。从（7）与氢化三正丁基锡的反应中分离出衍生自这两种中间体的产物。