(Z)-2-(4-methylbenzyl)-3-phenylacrylonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-2-(4-methylbenzyl)-3-phenylacrylonitrile
• 英文别名: 2-(4'-methylbenzyl)-3-phenylacrylonitrile；(Z)-2-[(4-methylphenyl)methyl]-3-phenylprop-2-enenitrile
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: BMWCEGCRAWCIFK-BOPFTXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-acetoxy-2-methylene-3-phenylpropionitrile 、 potassium (4-methylphenyl)trifluoroborate 在 palladium diacetate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到(Z)-2-(4-methylbenzyl)-3-phenylacrylonitrile
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Acetates of Baylis−Hillman Adducts and Potassium Organotrifluoroborates

  摘要：

  [GRAPHICS]The cross-coupling of potassium organotrifluoroborates and acetates of Baylis-Hillman adducts proceeds readily in moderate to excellent yield in the presence of Pd(OAc)(2). The reaction tolerates hindered trifluoroborate salts, and the process is stereoselective.

  DOI：

  10.1021/ol0351798

文献信息

• Chemo-, regio- and stereoselective addition of triorganoindium reagents to acetates of Baylis–Hillman adducts: a new strategy for the synthesis of (E)- and (Z)-trisubstituted alkenes
  作者：Brindaban C. Ranu、Kalicharan Chattopadhyay、Ranjan Jana

  DOI：10.1016/j.tetlet.2007.03.154

  日期：2007.5

  The addition of several trialkyl or triarylindium reagents to the acetates of Baylis–Hillman adducts proceeds readily under the catalysis of copper and palladium derivatives. The reactions of trialkylindiums are catalyzed efficiently by CuI whereas additions of triarylindiums produce better results with Pd(PPh3)4. The reactions with 3-acetoxy-2-methylenealkanoates provide (E)-alkenes, whereas similar

  在铜和钯衍生物的催化下，向Baylis-Hillman加合物的乙酸酯中添加几种三烷基或三芳基鎓试剂很容易。CuI可以有效地催化三烷基铟的反应，而Pd（PPh 3）4可以增加三芳基铟的生成效果。与3-乙酰氧基-2-亚甲基链烷酸酯的反应提供了（E）-烯烃，而与3-乙酰氧基-2-亚甲基链烷烯腈的类似反应导致了（Z）-烯烃。所有反应都具有高度的区域选择性和立体选择性，并且产率高。
• Fe³⁺-K-10 Montmorillonite Clay Catalyzed Friedel–Crafts Reaction of Unactivated Baylis–Hillman Adducts: An Efficient Stereoselective Synthesis of Trisubstituted Alkenes Containing a Benzyl Substituent
  作者：Biswanath Das、Anjoy Majhi、Joydeep Banerjee、Nikhil Chowdhury、Katta Venkateswarlu

  DOI：10.1246/cl.2005.1492

  日期：2005.11

  The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel-Craft reaction of aromatic compounds with unactivated Baylis-Hillman adducts in the presence of Fe 3 + -K-10 montmorillonite clay as a heterogeneous catalyst. The catalyst can be recovered and reused.

  在 Fe 3 + -K-10 蒙脱石粘土作为非均相催化剂存在下，通过使用芳族化合物与未活化的 Baylis-Hillman 加合物的 Friedel-Craft 反应，实现了含有苄基取代基的三取代烯烃的立体选择性合成。催化剂可以回收再利用。
• Applications of the Baylis–Hillman reaction 2: a simple stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes
  作者：Deevi Basavaiah、Pakala K. S. Sarma、Anagani K. D. Bhavani

  DOI：10.1039/c39940001091

  日期：——

  Reaction of Grignard reagents with methyl 3-acetoxy-2-methylenealkanoates produces (2E)-2-substituted alk-2-enoates, whereas a similar reaction with 3-acetoxy-2-methylenealkanenitriles provides (2Z)-2-substituted alk-2-enenitriles in high (Z)-stereoselectivity.

  格氏试剂与 3-乙酰氧基-2-亚甲基烷酸甲酯反应生成(2E)-2-取代的烷-2-烯酸酯，而与 3-乙酰氧基-2-亚甲基烷腈的类似反应则以高(Z)-全选择性生成(2Z)-2-取代的烷-2-烯腈。
• Friedel-Crafts reaction of the Baylis-Hillman adducts of N -tosylimine derivatives
  作者：Hong Jung Lee、Mi Ra Seong、Jae Nyoung Kim

  DOI：10.1016/s0040-4039(98)01280-5

  日期：1998.8

  Friedel-Crafts reaction of aromatic compounds with the Baylis-Hillman adducts of N-tosylimine derivatives in the presence of sulfuric acid provided a stereoselective methodology for the preparation of 2-benzylsubstituted olefins in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An α-Diaminoboryl Carbanion Assisted Stereoselective Single-Pot Preparation of α,β<i>-</i>Disubstituted Acrylonitriles
  作者：Takashi Tomioka、Rambabu Sankranti、Trey G. Vaughan、Toshihide Maejima、Takayoshi Yanase

  DOI：10.1021/jo201280x

  日期：2011.10.7

  An alpha-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of alpha,beta-disubstituted acrylonitriles in a stereoselective manner. The protocol involves the formation of an alpha-substituted alpha-diaminoboryl acetonitrile and subsequent olefination with an aldehyde. The use of an aryl or conjugated aldehyde preferentially leads to a (Z)-acrylonitrile, while an aliphatic aldehyde gave an (E)-isomer as a major product. Two complementary approaches, a linear method and a divergent method, are developed.