(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene | 330988-80-2

• 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: (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene
• 英文别名: posticlure；(11S,12S)-(-)-posticlure；(2S,3S)-2-[(1Z,4Z)-deca-1,4-dienyl]-3-nonyloxirane
• CAS: 330988-80-2
• 化学式: C₂₁H₃₈O
• 分子量: 306.532
• InChiKey: AZNAATMZDDJQSS-SCMRAZOXSA-N

物化性质

• 沸点：
  399.5±11.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

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：

  (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene 在 diimide 作用下， 反应 1.0h， 生成 (11S,12S)-trans-10,11-epoxyhenicosane
  参考文献：
  名称：

  Posticlure: a novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker)

  摘要：

  A single EAG-active component was found in a pheromone extract from virgin females of the tussock moth, Orgyia postica. This compound nam ed posticlure possesses a trans-epoxy ring and was identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene by means of GC-MS, H-1 NMR and chiral HPLC analyses, and further chemical derivation followed by the GC-MS analysis. In a field test with. the pheromone synthesized stereoselectively, the male moths were specifically attracted to the (11S,12S)-isomer but not to the antipode. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02038-4
• 作为产物：
  描述：

  顺-3-壬烯-1-醇 在 四氧化锇 、 甲基磺酰胺 咪唑 、 (DHQ)2-PHAL 、 乙酰溴 、 碘 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 lithium hexamethyldisilazane 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 52.5h， 生成 (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene
  参考文献：
  名称：

  （+）-和（-）-邮编的不对称二羟基化和一锅环氧化途径：一种新的反式环氧化合物，作为Orgyia postica（Walker）的性信息素成分

  摘要：

  已经实现了（+）-和（-）-后诱变的高度对映选择性合成。合成的关键步骤是Sharpless不对称二羟基化反应和一锅环氧化反应。

  DOI：

  10.1016/s0040-4020(02)00685-3

文献信息

• An Efficient Synthesis of (–)-Posticlure: The Sex Pheromone ofOrgyia postica
  作者：Rodney A. Fernandes

  DOI：10.1002/ejoc.200700449

  日期：2007.10

  An efficient multigram synthesis of (–)-posticlure, the first trans-epoxide sex pheromone found in Orgyia postica, from diethyl L-tartrate is described. The synthesis was completed in seven steps and 27 % overall yield. The synthetic strategy features double-Wittig olefination and a stereoselective one-pot conversion of diol to epoxide as the key steps. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  描述了从 L-酒石酸二乙酯中高效合成 (-)-posticlure，这是在 Orgyia postica 中发现的第一种反式环氧化物性信息素。合成分七个步骤完成，总产率为 27%。该合成策略以双维蒂希烯化和二醇立体选择性一锅法转化为环氧化物为关键步骤。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A General Method for the Synthesis of Nonracemic <i>trans</i>-Epoxides:  Concise Syntheses of <i>trans</i>-Epoxide-Containing Insect Sex Pheromones
  作者：Baldip Kang、Robert Britton

  DOI：10.1021/ol702273n

  日期：2007.11.1

  developed that provides rapid access to alkyl-, alkenyl-, alkynyl-, and phenyl-substituted trans-epoxides from aldehydes. This methodology has also been applied in concise and high-yielding syntheses of both trans-epoxide containing insect sex pheromones.

  已经开发了用于合成手性非外消旋反式环氧化物的通用方法，该方法提供了从醛类快速进入烷基，烯基，炔基和苯基取代的反式环氧化物的途径。该方法也已用于含有反式环氧化物的昆虫性信息素的简明和高产合成中。
• Sex Pheromone and Related Compounds in the Ishigaki and Okinawa Strains of the Tussock Moth<i>Orgyia postica</i>(Walker) (Lepidoptera: Lymantriidae)
  作者：Sadao WAKAMURA、Norio ARAKAKI、Masanobu YAMAMOTO、Syuntaro HIRADATE、Hiroe YASUI、Kunio KINJO、Tetsuya YASUDA、Hiroyuki YAMAZAWA、Tetsu ANDO

  DOI：10.1271/bbb.69.957

  日期：2005.1

  Two distinct electroantennographycally active (EAG-active) components, A and B, and a weakly active component C were found in a solvent extract from virgin females of the Ishigaki strain of the tussock moth, Orgyia postica (Walker). Components A, B, and C were found in the extract of the females at 4.0, 0.5, and 4.0 ng/female respectively. Components A, B, and C were identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene [(11S,12S)-1: posticlure], (6Z)-henicos-6-en-11-one (2), and (6Z,9Z)-henicosa-6,9-diene (3), respectively. Component B was absent in the extract from the Okinawa strain, in which components A and C were present at 2.0 and 1.5 ng/female respectively. (11S,12S)-1 and the racemic mixture showed attractiveness for both the Okinawa and Ishigaki strains, whereas (11R,12R)-1 did not. The addition of 2 significantly reduced the trap catches with (11S,12S)-1 on the Okinawa strain which lacked 2, while there was no significant inhibitory effect on the Ishigaki strain. The addition of 3 to (11S,12S)-1 did not significantly affect trap catches at Ishigaki or Okinawa. This confirmed that the attractant pheromone of O. postica of the Ishigaki strain is also (11S,12S)-1.

  在石垣株草履蛾（Orgyia postica (Walker)）雌性处女的溶剂提取物中发现了两种不同的电图活性（EAG-active）成分 A 和 B，以及一种弱活性成分 C。雌虫提取物中 A、B 和 C 的含量分别为 4.0、0.5 和 4.0 纳克/雌虫。经鉴定，成分 A、B 和 C 分别为 (6Z,9Z,11S,12S)-11,12-环氧henicosa-6,9-diene[(11S,12S)-1: posticlure]、(6Z)-henicos-6-en-11-one (2) 和 (6Z,9Z)-henicosa-6,9-diene (3)。冲绳菌株的提取物中没有成分 B，其中成分 A 和 C 的含量分别为 2.0 纳克/雌株和 1.5 纳克/雌株。(11S,12S)-1和外消旋混合物对冲绳和石垣菌株都有吸引力，而(11R,12R)-1则没有。冲绳菌株缺乏 2，而石垣菌株则没有明显的抑制作用，添加 2 后，(11S,12S)-1 对冲绳菌株的诱捕率明显下降。在（11S,12S）-1 中添加 3 对石垣和冲绳的诱捕效果没有明显影响。这证实了石垣品系 O. postica 的引诱信息素也是 (11S,12S)-1。
• Synthesis of Posticlure [(6Z,9Z,11S,12S)-11,12-Epoxyhenicosa-6,9-diene], the Female Sex Pheromone of Orgyia postica
  作者：Shin-etsu Muto、Kenji Mori

  DOI：10.1002/1099-0690(200112)2001:24<4635::aid-ejoc4635>3.0.co;2-j

  日期：2001.12

  Starting from commercially available (E)-2-dodecenoic acid, posticlure [(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene (1)], the female sex pheromone of the tussock moth (Orgyia postica), was synthesized in 25% overall yield (6 steps) by employing Sharpless asymmetric dihydroxylation as the key step. Its (11R,12R)-isomer as well as its racemate were also synthesized.
• Asymmetric dihydroxylation and one-pot epoxidation routes to (+)- and (−)-posticlure: a novel trans-epoxide as a sex pheromone component of Orgyia postica (Walker)
  作者：Rodney A Fernandes、Pradeep Kumar

  DOI：10.1016/s0040-4020(02)00685-3

  日期：2002.8

  A highly enantioselective synthesis of (+)- and (−)-posticlure has been achieved. The synthesis features the Sharpless asymmetric dihydroxylation and one-pot epoxidation as the key steps.

  已经实现了（+）-和（-）-后诱变的高度对映选择性合成。合成的关键步骤是Sharpless不对称二羟基化反应和一锅环氧化反应。