cis-3,cis-6,cis-9,10-epoxyheneicosadiene

• 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: cis-3,cis-6,cis-9,10-epoxyheneicosadiene
• 英文别名: (3Z,6Z)-cis-9,10-epoxyhenicosa-3,6-diene；(Z,Z)-(+/-)-cis-2-(2,5-Octadiynyl)-3-undecyloxirane；9S,10R-Epoxy-3Z,6Z-heneicosadiene；(2R,3S)-2-[(2Z,5Z)-octa-2,5-dienyl]-3-undecyloxirane
• 化学式: C₂₁H₃₈O
• 分子量: 306.532
• InChiKey: HQCGSJRACGWHOF-LXOZGROOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  cis-3,cis-6,cis-9,10-epoxyheneicosadiene 在 2-甲基-4-氯苯氧乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54%的产率得到(3R,4S,9R,10S)-(6Z)-cis-3,4-cis-9,10-diepoxy-6-henicosene
  参考文献：
  名称：

  摘要：

  All stereoisomers of three diepoxyalkenes derived from (3Z,6Z,9Z)-trienes with a C-21, C-19, or C-18 straight chain, lymantriid sex pheromones and their candidates, were synthesized by MCPBA oxidation of optically active epoxyalkadienes. Their chromatographic behaviors were examined with GC and LC equipped with achiral and chiral columns. Detailed inspection of the mass spectra of these epoxides indicated the following diagnostic ions for determining the chemical structures: m/z 128, 167, M-87 and M-85 for (Z)-cis-3,4-cis-6,7-diepoxy-9-enes; m/z 111, M-125 and M-69 for (Z)-cis-6,7-cis-9,10-diepoxy3-enes; and m/z M-125 and M-139 for (Z)-cis-3,4-cis-9,10-diepoxy-6-enes. Mass chromatographic analysis that monitored these fragment ions revealed the existence of a new pheromonal compound with a C-21 chain in an extract from virgin females of a lymantriid species, Perina nuda F. The three diepoxyalkenes were converted into the corresponding DMDS adducts, which showed characteristic ions from fragmentation between the two thiomethyl groups, reflecting the position of an original double bond.

  DOI：

  10.1023/a:1012255201380
• 作为产物：
  描述：

  1-溴十一烷 在 sodium tetrahydroborate 、 正丁基锂 、 乙基溴化镁 、 氢气 、 nickel diacetate 、 lithium 、 乙二胺 、 对甲苯磺酰氯 、 间氯过氧苯甲酸 、 copper(l) chloride 、 lithium chloride 作用下， 以 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 cis-3,cis-6,cis-9,10-epoxyheneicosadiene
  参考文献：
  名称：

  Nikolaeva, L. A.; Kovalev, B. G., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, p. 676 - 679

  摘要：

  DOI：

文献信息

• Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3z,6z)--9,10-epoxy-3,6-heneicosadiene
  作者：Kenji Mori、Takashi Ebata

  DOI：10.1016/s0040-4020(01)87314-2

  日期：1986.1

  (+)-Disparlure 1 and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3, 6-heneicosadiene 2 were synthesized in optically pure forms employing the Sharpless asymmetric epoxidation as the key-step. The natural pheromone 2 isolated from Estigmene acrea was shown to possess (9S,10R)-stereochemistry.

  以（Sharpless）不对称环氧化为关键步骤，以光学纯净的形式合成了（+）-Disparlure 1和（3Z，6Z）-cis-9,10-epoxy-3，6-heneicosadiene 2的对映体。分离自Estigmene acrea的天然信息素2具有（9S，10R）-立体化学。
• Synthesis of optically active pheromones with an epoxy ring, (+)-disparlure and the saltmarsh caterpillar moth pheromone [()-3,6--1-9,10-epoxyheneicosadiene]
  作者：Kenji Mori、Takashi Ebata

  DOI：10.1016/s0040-4039(01)82934-8

  日期：1981.1
• Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones
  作者：Thomas W. Bell、James A. Ciaccio

  DOI：10.1021/jo00071a026

  日期：1993.9

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.
• NIKOLAEVA, L. A.;KOVALEV, B. G., ZH. ORGAN. XIMII, 1985, 21, N 4, 746-750
  作者：NIKOLAEVA, L. A.、KOVALEV, B. G.

  DOI：——

  日期：——
• BELL, THOMAS W.;CIACCIO, JAMES A., TETRAHEDRON LETT., 29,(1988) N 8, 865-868
  作者：BELL, THOMAS W.、CIACCIO, JAMES A.

  DOI：——

  日期：——