11-(四氢-2-吡喃氧基)-(9E,11Z)-十六碳二烯 | 176784-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 11-(四氢-2-吡喃氧基)-(9E,11Z)-十六碳二烯
• 英文名称: 11-(tetrahydro-2-pyranyloxy)-(9E,11Z)-hexadecadiene
• 英文别名: 2-[(9E,11Z)-hexadeca-9,11-dienoxy]oxane
• CAS: 176784-62-6
• 化学式: C₂₁H₃₈O₂
• 分子量: 322.532
• InChiKey: SSTUPPBKNZKNLX-IGTJQSIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-(四氢-2-吡喃氧基)-(9E,11Z)-十六碳二烯 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (9E,11Z)-hexadecadienal
  参考文献：
  名称：

  Sex attractant pheromone of the pecan nut casebearer (Lepidoptera: Pyralidae)

  摘要：

  A female-produced sex pheromone for the pecan nut casebearer, Acrobasis nuxvorella Neunzig, has been identified from pheromone gland extracts of calling female moths. The compound (9E,11Z)-hexadecadienal [(9E,11Z)-16:Ald] was identified by coupled GC-EAD and retention time matches with a synthetic standard on four capillary GC columns of different polarities. Corroboration of the identification of (9E, 11Z)-16:Ald by other analytical chemistry methods was not possible due to the minute quantities of pheromone extracted (<1 picogram/female). In field studies, gray rubber septa impregnated with 100 mu g of synthetic (9E,11Z)-16:Ald were attractive to male moths, whereas higher and lower doses were less attractive. The homologous (9E,11Z)-15:Ald was also slightly attractive, while the more highly conjugated analogues, (9E,11Z,13Z)- and (9E, 11Z,13E)-16:Ald, were not. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00010-7
• 作为产物：
  描述：

  11-(tetrahydro-2-pyranyloxy)undec-2-yn-1-ol 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 11-(四氢-2-吡喃氧基)-(9E,11Z)-十六碳二烯
  参考文献：
  名称：

  鉴定，合成和表征9.11-十六碳烯醛的几何异构体，其来自甘蔗钻Dia糖的雌性信息素腺。

  摘要：

  对甘蔗蛀虫Diatraea saccharalis的信息素腺的化学分析表明，除了十六烷醛和（Z）-hexadec-11-enal之外，还存在9,11-十六二烯醛（1-4）的四种几何异构体。我们在这里报告了化合物1-4的合成与表征。一种原料9-癸烯-1-醇已用于通过不同的合成途径获得所有这些原料。

  DOI：

  10.1021/np010551i

文献信息

• Sex attractant pheromone of the pecan nut casebearer (Lepidoptera: Pyralidae)
  作者：Jocelyn G. Millar、Allen E. Knudson、J.Steven McElfresh、Regine Gries、Gerhard Gries、James H. Davis

  DOI：10.1016/0968-0896(96)00010-7

  日期：1996.3

  A female-produced sex pheromone for the pecan nut casebearer, Acrobasis nuxvorella Neunzig, has been identified from pheromone gland extracts of calling female moths. The compound (9E,11Z)-hexadecadienal [(9E,11Z)-16:Ald] was identified by coupled GC-EAD and retention time matches with a synthetic standard on four capillary GC columns of different polarities. Corroboration of the identification of (9E, 11Z)-16:Ald by other analytical chemistry methods was not possible due to the minute quantities of pheromone extracted (<1 picogram/female). In field studies, gray rubber septa impregnated with 100 mu g of synthetic (9E,11Z)-16:Ald were attractive to male moths, whereas higher and lower doses were less attractive. The homologous (9E,11Z)-15:Ald was also slightly attractive, while the more highly conjugated analogues, (9E,11Z,13Z)- and (9E, 11Z,13E)-16:Ald, were not. Copyright (C) 1996 Elsevier Science Ltd
• Identification, Syntheses, and Characterization of the Geometric Isomers of 9,11-Hexadecadienal from Female Pheromone Glands of the Sugar Cane Borer <i>Diatraea saccharalis</i>
  作者：Ellen M. Santangelo、Myrian Coracini、Peter Witzgall、Arlene G. Correa、C. Rikard Unelius

  DOI：10.1021/np010551i

  日期：2002.6.1

  Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.

  对甘蔗蛀虫Diatraea saccharalis的信息素腺的化学分析表明，除了十六烷醛和（Z）-hexadec-11-enal之外，还存在9,11-十六二烯醛（1-4）的四种几何异构体。我们在这里报告了化合物1-4的合成与表征。一种原料9-癸烯-1-醇已用于通过不同的合成途径获得所有这些原料。