(Z)-2-(4-methylbenzylidene)hex-5-enenitrile | 1026729-40-7

• 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: (Z)-2-(4-methylbenzylidene)hex-5-enenitrile
• 英文别名: (2Z)-2-[(4-methylphenyl)methylidene]hex-5-enenitrile
• CAS: 1026729-40-7
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: BHUHVFCBKKXLKC-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  Acetic acid 2-cyano-1-p-tolyl-allyl ester 、 3-溴丙烯 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-2-(4-methylbenzylidene)hex-5-enenitrile 、 (Z)-2-(4-methylbenzylidene)hex-5-enenitrile
  参考文献：
  名称：

  Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

  摘要：

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.

  DOI：

  10.1021/jo800049p

文献信息

• Boron Trifluoride-Diethyl Etherate Complex Mediated Allylation of Baylis-Hillman Adducts: A Facile Synthesis of 1,5-Dienes
  作者：Jhillu Yadav、Basi Reddy、Satadru Mandal、Ashutosh Singh、Ashok Basak

  DOI：10.1055/s-2008-1067049

  日期：——

  Morita-Baylis-Hillman adducts undergo smooth allylic nucleophilic substitution (S N 2′) with allyltrimethylsilane in the presence of BF 3 ·OEt 2 under mild reaction conditions to afford 1,5-diene derivatives in good yields with high selectivity.

  Morita-Baylis-Hillman 加合物在BF 3 ·OEt 2 存在下，在温和的反应条件下用烯丙基三甲基硅烷进行平滑的烯丙基亲核取代(SN 2')，以高收率和高选择性得到1,5-二烯衍生物。
• Efficient Palladium-Catalyzed Coupling of Baylis-Hillman Acetates with an Allylstannane
  作者：Cheol Yoon、Jinhyung Park、Young Kwon、Kyungmo Yang、Hakjune Rhee

  DOI：10.1055/s-0029-1218612

  日期：2010.2

  Acetates of Baylis-Hillman adducts derived from ethyl acrylate, methyl vinyl ketone, and acrylonitrile were coupled with allyltributylstannane using Pd(PPh3)4 or Pd(dba)2 as the catalyst at room temperature to afford the corresponding trisubstituted alka-1,5-dienes in good to high yields.

  从乙基丙烯酸酯、甲基烯基酮和丙烯腈衍生的 Baylis-Hillman 加合物的醋酸盐与烯丙基四丁基锡在室温下使用 Pd(PPh3)4 或 Pd(dba)2 作为催化剂偶联，得到相应的三取代烯-1,5-二烯，产率良好至很高。
• Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones
  作者：Samir K. Mandal、Moumita Paira、Subhas C. Roy

  DOI：10.1021/jo800049p

  日期：2008.5.1

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.