rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane | 97668-96-7

• 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: rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane
• 英文别名: (3Z,6Z)-cis-9,10-epoxynonadeca-3,6-diene；(Z,Z)-cis-9,10-epoxy-3,7-nonadecadiene；9S,10R-Epoxy-3Z,6Z-nonadecadiene；(2S,3R)-2-nonyl-3-[(2Z,5Z)-octa-2,5-dienyl]oxirane
• CAS: 97668-96-7；97718-63-3；97719-75-0；114247-67-5；129939-19-1
• 化学式: C₁₉H₃₄O
• 分子量: 278.478
• InChiKey: CEWBAXULNPORDY-PZKRYTKLSA-N

物化性质

• 沸点：
  360.6±11.0 °C(Predicted)
• 密度：
  0.866±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3R,4S,6R,7S)-(9Z)-cis-3,4-cis-6,7-diepoxy-9-nonadecene 、 (6R,7S,9S,10R)-(3Z)-cis-6,7-cis-9,10-diepoxy-3-nonadecene 、 (3S,4R,6R,7S)-(9Z)-cis-3,4-cis-6,7-diepoxy-9-nonadecene
  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：

  Γ-十八碳三烯酸 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 生成 rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane
  参考文献：
  名称：

  Identification and enantioselective synthesis of (Z,Z)-6,9-cis-3S,4R-epoxynonadecadiene, the major sex pheromone component of Boarmia selenaria

  摘要：

  DOI：

  10.1016/s0040-4039(00)97770-0

文献信息

• Improved Synthesis and Deployment of (2<i>S</i>,3<i>R</i>)-2-(2<i>Z</i>,5<i>Z</i>-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, <i>Lymantria mathura</i>
  作者：Ashot Khrimian、James E. Oliver、Roger C. Hahn、Nikki H. Dees、Jeff White、Victor C. Mastro

  DOI：10.1021/jf035506q

  日期：2004.5.1

  We report two new syntheses of (2S,3R)-2-(2Z5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in greater than or equal to37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.
• Identification and enantioselective synthesis of (Z,Z)-6,9-cis-3S,4R-epoxynonadecadiene, the major sex pheromone component of Boarmia selenaria
  作者：D. Becker、R. Cyjon、A. Cossé、I. Moore、T. Kimmel、M. Wysoki

  DOI：10.1016/s0040-4039(00)97770-0

  日期：1990.1
• ——
  作者：Hiroyuki Yamazawa、Naoto Nakajima、Sadao Wakamura、Norio Arakaki、Masanobu Yamamoto、Tetsu Ando

  DOI：10.1023/a:1012255201380

  日期：——

  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.