2-(3-cyanopropyl)hex-1-ene | 123004-96-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(3-cyanopropyl)hex-1-ene
• 英文别名: 5-butyl-5-hexenenitrile；5-Methylidenenonanenitrile
• CAS: 123004-96-6
• 化学式: C₁₀H₁₇N
• 分子量: 151.252
• InChiKey: GESIPSLICUECNN-UHFFFAOYSA-N

物化性质

• 沸点：
  234.9±19.0 °C(Predicted)
• 密度：
  0.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴丁基-镁 、 5-cyanopent-1-en-2-yl diphenyl phosphate 在 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 以96%的产率得到2-(3-cyanopropyl)hex-1-ene
  参考文献：
  名称：

  磷酸烯醇对格氏试剂的铁催化烯基化

  摘要：

  通过在 Fe(acac) 3 存在下仅使 E-异构体与格氏试剂反应，可以很容易地从烯醇磷酸酯的 Z/E-混合物进行三取代烯烃的立体选择性制备。该过程结合了动力学微分和立体选择性反应。在烷基氯、酯、酮或腈的存在下，偶联是非常化学选择性的。

  DOI：

  10.1055/s-2008-1067194

文献信息

• Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00062a010

  日期：1993.5

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.
• Zinc and copper carbenoids as efficient and selective a1/d1 multicoupling reagents. 1
  作者：Paul Knochel、Nakcheol Jeong、Michael J. Rozema、Ming Chang P. Yeh

  DOI：10.1021/ja00198a097

  日期：1989.8
• Iron-Catalyzed Alkenylation of Grignard Reagents by Enol Phosphates
  作者：Gérard Cahiez、Olivier Gager、Vanessa Habiak

  DOI：10.1055/s-2008-1067194

  日期：2008.8

  Stereoselective preparation of trisubstituted olefins can be easily performed from an Z/E-mixture of enol phosphates by reacting only the E-isomer with a Grignard reagent in the presence of Fe(acac) 3 . This procedure combines a kinetic differentiation and a stereoselective reaction. The coupling is very chemoselective in the presence of an alkyl chloride, an ester, a ketone or a nitrile.

  通过在 Fe(acac) 3 存在下仅使 E-异构体与格氏试剂反应，可以很容易地从烯醇磷酸酯的 Z/E-混合物进行三取代烯烃的立体选择性制备。该过程结合了动力学微分和立体选择性反应。在烷基氯、酯、酮或腈的存在下，偶联是非常化学选择性的。