(E)-2,2,4-Trimethyl-5-phenyl-4-pentenenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2,2,4-Trimethyl-5-phenyl-4-pentenenitrile
• 英文别名: (E)-2,2,4-trimethyl-5-phenylpent-4-enenitrile
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: ZRQAPCAVCJMPFR-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2,2,4-Trimethyl-5-phenyl-4-pentenenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以93%的产率得到(E)-2,2,4-trimethyl-5-phenylpent-4-enylamine
  参考文献：
  名称：

  Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups

  摘要：

  A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(2)](3) (1(Y)). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl) furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.

  DOI：

  10.1055/s-0032-1317843
• 作为产物：
  描述：

  ethyl (E)-2-methyl-3-phenyl-2-propenoate 在 lithium aluminium tetrahydride 、 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 14.5h， 生成 (E)-2,2,4-Trimethyl-5-phenyl-4-pentenenitrile
  参考文献：
  名称：

  Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups

  摘要：

  A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(2)](3) (1(Y)). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl) furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.

  DOI：

  10.1055/s-0032-1317843

文献信息

• Iron-Mediated C-C Bond Formation. Preparation of (Trimethylenemethane)iron Complexes via Reaction of Weak Carbon Nucleophiles with in Situ Generated Cross-Conjugated Pentadienyl Cations. Nucleophilic Attack on (Trimethylenemethane)iron Complexes with Carbanions
  作者：William A. Donaldson、M. Azad Hossain、Charles D. Cushnie

  DOI：10.1021/jo00111a019

  日期：1995.3

  The reaction of (2-(acetoxymethylene)-1,3-butadiene)Fe(CO)(3) (8) or ((acetoxymethylene)trimethylenemethane)Fe(CO)(3) (9) with weak carbon nucleophiles in the presence of BF3 . Et(2)O gives the corresponding substituted (trimethylenemethane)Fe(CO)(3) complexes as the major product. Applicable nucleophiles include trialkylaluminums, allyltrimethylsilane, and 2-((trimethylsilyl)oxy)-1-propene. This reaction proceeds in a stereospecific fashion; reaction of 12 gives a single (trimethylenemethane)iron product. The reaction of (1,2-bis(acetoxymethylene)-1,3-butadiene)Fe-(CO)(3) (20) with allyltrimethylsilane gives a (TMM)Fe(CO)(3) product in which two new C-C bonds have been formed in one reaction. Reaction of TMMFe(CO)(3) (1a) and substituted derivatives with carbanions, followed by workup with trifluoroacetic acid, gives the corresponding methallylated product. Applicable nucleophiles include anions derived from diphenylmethane, ethyl isobutyrate, isobutylnitrile, and 2-phenyl-1,3-dithiane. Use of allyl bromide in place of trifluoroacetic acid gives 6-substituted 5-methylene-1-hexenes as products, the result of a three-component coupling.
• Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups
  作者：Tom Livinghouse、Tao Jiang、Khoi Huynh

  DOI：10.1055/s-0032-1317843

  日期：——

  A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(2)](3) (1(Y)). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl) furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.