(2E)-bromo-3,7-dimethyl-6-epoxy-octa-2-ene | 106820-22-8

• 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: (2E)-bromo-3,7-dimethyl-6-epoxy-octa-2-ene
• 英文别名: (R,E)-3-(5-bromo-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane；(R)-6,7-epoxygeranyl bromide；6,7-epoxygeranyl bromide；(3R)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2,2-dimethyloxirane
• CAS: 106820-22-8
• 化学式: C₁₀H₁₇BrO
• 分子量: 233.148
• InChiKey: QSIYEVLJDXOHMD-BNICOGTQSA-N

物化性质

• 沸点：
  253.1±13.0 °C(predicted)
• 密度：
  1.208±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  (2E)-bromo-3,7-dimethyl-6-epoxy-octa-2-ene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 aluminum tri-bromide 、 二乙胺 、 pyridinium chlorochromate 、 二溴甲烷 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 62.5h， 生成 trimethyl{[(4aR,8aS)-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethynyl}silane
  参考文献：
  名称：

  从通过仿生阳离子环化获得的普通对映体纯支架构建多样化的萜烯十氢化萘亚基组†

  摘要：

  含有炔烃的香叶醇衍生的环氧化物的前所未有的仿生阳离子环化反应可用于立体选择性合成新型对映体纯的骨架，该骨架很容易转化为一组结构多样的十氢化萘衍生物，并可能在合成目标天然产物和/或灵感来自天然产物的新分子。

  DOI：

  10.1039/c8cc07281g
• 作为产物：
  描述：

  (R,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到(2E)-bromo-3,7-dimethyl-6-epoxy-octa-2-ene
  参考文献：
  名称：

  光学上的番茄红素-环氧和番茄红素-甘醇：合成与手足病本征疗法

  摘要：

  光学活性番茄红素环氧树脂和番茄红素乙二醇：合成和手性性质

  DOI：

  10.1002/hlca.19860690114

文献信息

• Optisch aktive Lycopin-epoxide und Lycopin-glycole: Synthesen und chiroptische Eigenschaften
  作者：Heidi Meier、Peter Uebelhart、Conrad Hans Eugster

  DOI：10.1002/hlca.19860690114

  日期：1986.2.5

  Optically Active Lycopene Epoxides and Lycopene Glycols: Synthesis and Chiroptical Properties

  光学活性番茄红素环氧树脂和番茄红素乙二醇：合成和手性性质
• Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A
  作者：Joseph J. Topczewski、John G. Kodet、David F. Wiemer

  DOI：10.1021/jo1022102

  日期：2011.2.4

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.
• Relevance of the C-5 position to schweinfurthin induced cytotoxicity
  作者：Joseph J. Topczewski、Michael P. Callahan、John G. Kodet、Jery D. Inbarasu、Nolan R. Mente、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2011.10.034

  日期：2011.12

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.
• Construction of a diverse set of terpenoid decalin subunits from a common enantiomerically pure scaffold obtained by a biomimetic cationic cyclization
  作者：Raquel Fontaneda、Francisco J. Fañanás、Félix Rodríguez

  DOI：10.1039/c8cc07281g

  日期：——

  An unprecedented biomimetic cationic cyclization reaction of an alkyne-containing geraniol-derived epoxide is used for the stereoselective synthesis of a novel enantiomerically pure scaffold that is easily transformed into a set of structurally diverse decalin derivatives with potential application in the synthesis of targeted natural products and/or natural-product-inspired new molecules.

  含有炔烃的香叶醇衍生的环氧化物的前所未有的仿生阳离子环化反应可用于立体选择性合成新型对映体纯的骨架，该骨架很容易转化为一组结构多样的十氢化萘衍生物，并可能在合成目标天然产物和/或灵感来自天然产物的新分子。
• Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation
  作者：Jeffrey D. Neighbors、Nolan R. Mente、Kelly D. Boss、Donald W. Zehnder、David F. Wiemer

  DOI：10.1016/j.tetlet.2007.11.086

  日期：2008.1

  Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B. (C) 2007 Elsevier Ltd. All rights reserved.