(Z)-henicos-6-ene | 93662-67-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (Z)-henicos-6-ene
• CAS: 93662-67-0
• 化学式: C₂₁H₄₂
• 分子量: 294.564
• InChiKey: JCWFSHNSRREWAZ-QBFSEMIESA-N

物化性质

• 沸点：
  151-153 °C(Press: 1 Torr)
• 密度：
  0.798±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-henicos-6-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 cis-6,7-epoxyhenicosane
  参考文献：
  名称：

  摘要：

  Four EAG-active components (A-D) were found in the solvent extract of virgin females of the clear-winged tussock moth, Perina nuda, The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,4S,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C): and its 3S,4R,6S,7R isomer, (D): with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to mate moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. In this field test, noctuid Hypocala rostrata males were also attracted with the synthetic P. nuda pheromone.

  DOI：

  10.1023/a:1014545309128
• 作为产物：
  描述：

  溴代十四烷 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 氢气 作用下， 以 Petroleum ether 为溶剂， 反应 2.5h， 生成 (Z)-henicos-6-ene
  参考文献：
  名称：

  The Synthesis of Long Chain Dialkylalkynes, Dialkyldiynes and Their Hydrogenation to Monoenes and Dienes

  摘要：

  Long methylenic chain dialkylalkynes have been synthesised in high yield by an improved procedure. The methodology has been extended to nonconjugated diynes. Catalytic hydrogenation with a poisoned palladium catalyst affords cis-monoenes and cis,cis-dienes respectively. An improved synthesis of cis-9-tricosene is described.

  DOI：

  10.1080/00397919808006830

文献信息

• A convenient reduction of alkylated tosylmethyl isocyanides
  作者：J.S. Yodov、P.Satyanarayana Ready、Bhalchandra V. Joshi

  DOI：10.1016/s0040-4020(01)86095-6

  日期：1988.1

  A convenient and simple method for the reduction of mono- and diatkylated tosylmethyl isocyanides with lithium in liquid ammonia to corresponding hydrocarbons is described. The utility of this methodology adopted in the synthesis of tricos-9Z-ene. (7g), a. sex pheromone of common house fly, (-)-1S.5R, 7S-exo-brevicomin (17), an antipode of sex pheromone of Western pine beetle and (4S,5S)-5-hydroxy-4-decanolide

  描述了一种方便和简单的方法，用于在液态氨中用锂将单和二烷基化的甲苯磺酰基甲基异氰化物还原为相应的烃。在Tricos-9Z-ene的合成中采用了这种方法。（7克）普通家蝇的性信息素，（-）-1S.5R，7S-exo-brevicomin（17），西松甲虫性信息素的对映体和（4S，5S）-5-羟基-4-癸内酯（L-因子，19），一种用于白细胞霉素生物合成的拟议的自动调节剂。
• A convenient reduction of dialkylated tosylmethyl isocyanide
  作者：J.S. Yadav、P.Satyanarayana Reddy

  DOI：10.1016/0040-4039(84)80057-x

  日期：——

  Dialkylated tosylmethyl isocyanides have been conveniently reduced to the corresponding hydrocarbons with lithium in liquid ammonia. This process has been successfully utilised in the synthesis of (Z)-9-tricosene - a sex pheromone of common house fly.

  二烷基化的甲苯磺酰基甲基异氰化物已方便地在液态氨中用锂还原为相应的烃。该方法已成功用于合成（Z）-9-三苯三酚-普通家蝇的性信息素。
• The Synthesis of Long Chain Dialkylalkynes, Dialkyldiynes and Their Hydrogenation to Monoenes and Dienes
  作者：I. G. Fisher、J. H. P. Tyman

  DOI：10.1080/00397919808006830

  日期：1998.4

  Long methylenic chain dialkylalkynes have been synthesised in high yield by an improved procedure. The methodology has been extended to nonconjugated diynes. Catalytic hydrogenation with a poisoned palladium catalyst affords cis-monoenes and cis,cis-dienes respectively. An improved synthesis of cis-9-tricosene is described.
• ——
  作者：Sadao Wakamura、Norio Arakaki、Hiroyuki Yamazawa、Naoto Nakajima、Masanobu Yamamoto、Tetsu Ando

  DOI：10.1023/a:1014545309128

  日期：——

  Four EAG-active components (A-D) were found in the solvent extract of virgin females of the clear-winged tussock moth, Perina nuda, The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,4S,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C): and its 3S,4R,6S,7R isomer, (D): with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to mate moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. In this field test, noctuid Hypocala rostrata males were also attracted with the synthetic P. nuda pheromone.