(2S,3R)-3-(溴甲基)-2-甲基-2-(4-甲基戊-3-烯-1-基)环氧乙烷 | 91423-24-4

• 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: (2R,3S)-2-Bromomethyl-3-(4-methyl-3-pentenyl)-oxirane
• 英文别名: (2R,3S)-2-bromomethyl-3-(4-methylpent-3-enyl)oxirane；(2S,3R)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane；(2S,3R)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-enyl)oxirane
• CAS: 91423-24-4
• 化学式: C₁₀H₁₇BrO
• 分子量: 233.148
• InChiKey: YBLCNHAYWVYVPC-UWVGGRQHSA-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 咪唑 、 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 三氟甲磺酸三甲基硅酯 、 mercury(II) diacetate 、 仲丁基锂 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 正壬烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺-d7 、 水 、 乙酸乙酯 为溶剂， 反应 8.12h， 生成 (3S,3aS,7R,7aS)-6,7a-dimethoxy-3-methyl-3-(4-methyl-4-((triethylsilyl)oxy)pentyl)-7-(3-methylbut-2-en-1-yl)-3,3a,7,7a-tetrahydro-2,7-methanobenzofuran-4(2H)-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of Hyperforin

  摘要：

  A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]-nonane core and set two key quaternary stereocenters.

  DOI：

  10.1021/ja312150d
• 作为产物：
  描述：

  香叶醇 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

• Effects of host plant,Gossypium hirsutum L., on sexual attraction of cabbage looper moths,Trichoplusia ni (Hübner) (Lepidoptera: Noctuidae)
  作者：P. J. Landolt、R. R. Heath、J. G. Millar、K. M. Davis-Hernandez、B. D. Dueben、K. E. Ward

  DOI：10.1007/bf02098402

  日期：1994.11

  Unmated female or male cabbage looper moths, Trichoplusia ni (Hubner), were attracted more often in a flight tunnel to a cage with moths of the opposite sex and a bouquet of cotton foliage. Increased sexual attractiveness of females with plants may be a result of stimulation of pheromone release in response to plant odor, since more males were attracted when odor of cotton foliage was passed over females than when odor of females was passed over cotton foliage before venting into the flight tunnel. Increased sexual attractiveness of males with plants is due in part to host odor enhancement of female attraction to male pheromone, since more females were attracted to synthetic male pheromone (a blend of enantiomers of linalool and isomers of cresol) and a cotton leaf extract than were attracted to male pheromone alone. A short synthesis procedure was developed for (S)-(+)-linalool, the major component of the male sex pheromone, isolated from hair pencils, used in these tests.
• 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.
• Novel Enantioselective Synthesis of 1,3-Butadien-2-ylmethanols via Tandem Alkylbromide-epoxide Vinylations Using Dimethylsulfonium Methylide
  作者：Lilian Alcaraz、Katherine Cox、Andrew P. Cridland、Elizabeth Kinchin、James Morris、Stewart P. Thompson

  DOI：10.1021/ol0502329

  日期：2005.3.1

  The treatment of chiral trans-disubstituted and trisubstituted 2,3-epoxy-1-bromides with an excess of dimethylsulfonium methylide 1 affords the corresponding 1,3-butadien-2-ylmethanols in good to excellent yields via a double one-carbon homologation.
• Enantioselective Total Synthesis of Hyperforin
  作者：Brian A. Sparling、David C. Moebius、Matthew D. Shair

  DOI：10.1021/ja312150d

  日期：2013.1.16

  A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]-nonane core and set two key quaternary stereocenters.
• 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。