(E)-7-dodecen-5-yn-1-ol | 82751-00-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-7-dodecen-5-yn-1-ol
• 英文别名: (E)-dodec-7-en-5-yn-1-ol
• CAS: 82751-00-6
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: SMLDOZHEIBNZRN-AATRIKPKSA-N

物化性质

• 溶解度：
  二氯甲烷；

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-7-dodecen-5-yn-1-ol 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 正己烷 为溶剂， 生成 十二碳-5,7-二烯-1-醇
  参考文献：
  名称：

  Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.

  摘要：

  过去曾提出5,7-十二碳二烯-1-醇的4种异构体为松树蚕的性信息素。这些异构体是通过对1-己炔和5-己炔-1-醇的四氢吡喃醚进行立体选择性合成得到的。(5Z, 7Z)异构体是通过Chodkiewic Cadiot反应和随后的硼氢化反应合成的，而其他三种异构体则是通过包括使用二茂锆氢化物[Schwarz试剂(C5H5)2Zn(H)Cl]调控区域选择性偶联反应的新颖合成方法获得的。5,8-和5,9-十二碳二烯-1-醇也通过类似方法合成，以便与内源性性信息素的特性进行比较。

  DOI：

  10.1271/bbb1961.46.717
• 作为产物：
  描述：

  2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 对甲苯磺酸 、 二乙胺 作用下， 以 甲醇 为溶剂， 生成 (E)-7-dodecen-5-yn-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.

  摘要：

  过去曾提出5,7-十二碳二烯-1-醇的4种异构体为松树蚕的性信息素。这些异构体是通过对1-己炔和5-己炔-1-醇的四氢吡喃醚进行立体选择性合成得到的。(5Z, 7Z)异构体是通过Chodkiewic Cadiot反应和随后的硼氢化反应合成的，而其他三种异构体则是通过包括使用二茂锆氢化物[Schwarz试剂(C5H5)2Zn(H)Cl]调控区域选择性偶联反应的新颖合成方法获得的。5,8-和5,9-十二碳二烯-1-醇也通过类似方法合成，以便与内源性性信息素的特性进行比较。

  DOI：

  10.1271/bbb1961.46.717

文献信息

• Stereospecific synthesis of (Z)-13-hexadecen-11-YN-1-YL acetate
  作者：Renzo Rossi、Adriano Carpita

  DOI：10.1016/s0040-4020(01)91820-4

  日期：1983.1

  (Z)-13-hexadecen-11-yn-1-yl acetate (2), the sex pheromone of Thaumetopoea pytyocampa, and (5Z,7E)-5,7-dodecadien-1-ol (3), a sex pheromone component of Malacosoma disstria, have been prepared in high chemical and stereoisomeric purity by synthetic schemes involving the stereospeific coupling of ω-functionalized 1-alkynes with (Z)- or (E)-1-iodo-1-alkenes in the presence of a catalytic amount of (PPh3)4Pd

  （Z）-13-hexadecen-11-yn-1- ylacetate（2），丘陵丘脑梭菌的性信息素和（5Z，7E）-5,7-dodecadien-1-ol（3），性信息素通过合成方案制备高化学和立体异构纯度的疟原虫假体的组分，该合成方案涉及在α-烯烃存在下ω-官能化的1-炔与（Z）-或（E）-1-碘-1-烯的立体定向偶联。在相转移条件下催化量的（PPh 3）4 Pd和Cul。
• New type formation of 1,3-enynes (or internal alkynes) via coupling of organoboranes with alkynylcopper compounds mediated by copper(II)
  作者：Yuzuru Masuda、Kaname Sato

  DOI：10.1039/a800242h

  日期：——

  The copper(II)—mediated coupling reaction of alkenyldialkyl- or trialkyl-boranes with alkynylcopper compounds (generated in situ), in the presence of appropriate solvents and a small amount of water, gives (E)-1,3-enynes (or disubstituted alkynes) with various functional groups in reasonable yields.

  铜(II)介导的烯烃二烷基或三烷基硼酸盐与烷炔铜化合物（原位生成）的偶联反应，在适当溶剂和少量水的存在下，能够以合理的产率生成各种功能团的(E)-1,3-烯炔（或二取代烷炔）。
• Syntheses of (<i>Z,E</i>)-5,7-Dodecadienol and (<i>E</i>,<i>Z</i>)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth
  作者：Ashot Khrimian、Jerome A. Klun、Yousef Hijji、Yuri N. Baranchikov、Vladimir M. Pet'ko、Victor C. Mastro、Matthew H. Kramer

  DOI：10.1021/jf020472s

  日期：2002.10.1

  Efficient syntheses of (ZE)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semihydrogenation was greater than or equal to98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 degreesC were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.
• Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.
  作者：Tetsu AND、Manh HUYNH VU、Shigeo YOSHIDA、Nobutaka TAKAHASHI

  DOI：10.1271/bbb1961.46.717

  日期：——

  Four isomers of 5, 7-dodecadien-1-ol were previously proposed as being the sex pheromone of the pine moth. The isomers were stereoselectively synthesized from 1-hexyne and tetrahydropyranyl ether of 5-hexyn-1-ol. The (5Z, 7Z)-isomer was synthesized by a Chodkiewic Cadiot reaction followed by hydroboration, and other three isomers by novel synthetic methods including the addition of zirconocene hydride [Schwarz's reagent (C5H5)2Zn(H)Cl] to control the regioselective coupling reaction. The 5, 8- and 5, 9-dodecadien-1-ols were also synthesized by similar methods for comparison of their characteristics with the endogenous sex pheromone.

  过去曾提出5,7-十二碳二烯-1-醇的4种异构体为松树蚕的性信息素。这些异构体是通过对1-己炔和5-己炔-1-醇的四氢吡喃醚进行立体选择性合成得到的。(5Z, 7Z)异构体是通过Chodkiewic Cadiot反应和随后的硼氢化反应合成的，而其他三种异构体则是通过包括使用二茂锆氢化物[Schwarz试剂(C5H5)2Zn(H)Cl]调控区域选择性偶联反应的新颖合成方法获得的。5,8-和5,9-十二碳二烯-1-醇也通过类似方法合成，以便与内源性性信息素的特性进行比较。