(Z)-tridec-5-en-7-yne | 65960-07-8

• 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)-tridec-5-en-7-yne
• 英文别名: tridec-5c-en-7-yne
• CAS: 65960-07-8
• 化学式: C₁₃H₂₂
• 分子量: 178.318
• InChiKey: JFVFSUVQRYZSOM-LUAWRHEFSA-N

物化性质

• 沸点：
  249.0±9.0 °C(Predicted)
• 密度：
  0.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  (Z)-1-iodohex-1-ene 在 copper(l) iodide 、 二(氰基苯)二氯化钯 哌啶 、 copper(l) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 (Z)-tridec-5-en-7-yne
  参考文献：
  名称：

  Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature

  摘要：

  Copper iodide and weakly ligated palladium complexes PdCl2(RCN)(2) (R = Ph, Me) catalyzed efficiently the coupling reaction of vinyl chlorides with 1-alkynes in the presence of piperidine to give the corresponding conjugated enynes in good to excellent yields. The reaction takes place rapidly and cleanly at room temperature. Application to the synthesis of terbinafine which exhibits strong antimycotic activity has been realized. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00909-8

文献信息

• Highly general stereo-, regio-, and chemo-selective synthesis of terminal and internal conjugated enynes by the Pd-catalysed reaction of alkynylzinc reagents with alkenyl halides
  作者：Anthony O. King、Nobuhisa Okukado、Ei-ichi Negishi

  DOI：10.1039/c39770000683

  日期：——

  The reaction of an alkynylzinc chloride, readily obtainable from the corresponding alkynyl-lithium and anhydrous zinc chloride, with an alkenyl iodide or bromide in the presence of a catalytic amount of a Pd–phosphine complex provides the corresponding terminal or internal enyne in high yield, the stereospecificity of the reaction being 97%.

  在催化量的Pd-膦配合物存在下，易于从相应的炔基锂和无水氯化锌获得的炔基氯化锌与烯基碘化物或溴化物的反应可提供高产率的相应末端或内部烯炔，反应的立体特异性为97％。
• Insect sex pheromones: Palladium-catalyzed synthesis of aliphatic 1,3-enynes by reaction of 1-alkynes with alkenyl halides under phase transfer conditions
  作者：Renzo Rossi、Adriano Carpita、Maria G. Quirici、Maria L. Gaudenzi

  DOI：10.1016/0040-4020(82)80204-4

  日期：1982.1

  prepared in good yields by coupling reaction of 1-alkynes or ω-functionalized 1-alkynes halides in the presence of a catalytic amount of (PPh3)4Pd and Cul. The reactions, which were carried out under phase transfer conditions employing benzyltriethylammonium chloride as phase transfer agent, benzene as organic solvent and diluted aq NaOH as base, occurred with 100% stereospecificity when 1-halo-1-alkenes

  在催化量的（PPh 3）4 Pd和Cul存在下，通过1-炔烃或ω-官能化1-炔烃卤化物的偶合反应，已经以高收率制备了通式1的官能化1，3-酶。当使用定义构型的1-卤-1-烯烃时，以苄基三乙基氯化铵为相转移剂，苯为有机溶剂，稀NaOH水溶液为碱的相转移条件下发生的反应具有100％的立体特异性。这种偶联反应已被用于以高总产率制备一些纯昆虫性信息素组分或其前体。
• Alami, Mouâd; Ramiandrasoa, Parfait; Cahiez, Gérard, Synlett, 1998, # 3, p. 325 - 327
  作者：Alami, Mouâd、Ramiandrasoa, Parfait、Cahiez, Gérard

  DOI：——

  日期：——
• Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
  作者：Mouâd Alami、Benoit Crousse、Fabiola Ferri

  DOI：10.1016/s0022-328x(00)00909-8

  日期：2001.4

  Copper iodide and weakly ligated palladium complexes PdCl2(RCN)(2) (R = Ph, Me) catalyzed efficiently the coupling reaction of vinyl chlorides with 1-alkynes in the presence of piperidine to give the corresponding conjugated enynes in good to excellent yields. The reaction takes place rapidly and cleanly at room temperature. Application to the synthesis of terbinafine which exhibits strong antimycotic activity has been realized. (C) 2001 Elsevier Science B.V. All rights reserved.