(E)-2-(N-methylanilino)-4-phenyl-2-butenenitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-2-(N-methylanilino)-4-phenyl-2-butenenitrile
• 英文别名: (E)-2-(N-methylanilino)-4-phenylbut-2-enenitrile
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: AUBUPONDZVETIP-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(N-methylanilino)-4-phenyl-2-butenenitrile 在 palladium diacetate 、 碘苯 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到苯甲腈
  参考文献：
  名称：

  Conversion of α-Anilino Alkenenitriles to Amides by Chemoselective Palladium-Catalyzed Arylations

  摘要：

  α-苯胺基烯烃腈与碘苯在钯催化下反应生成酰胺和苯甲腈。提出了一种通用机制来解释氰基的化学选择性芳基化。

  DOI：

  10.1055/s-1997-5783
• 作为产物：
  描述：

  (E)-2-(methyl(phenyl)amino)-4-phenylbut-3-enenitrile 以0%的产率得到
  参考文献：
  名称：

  Chang Chih-Jung, Fang Jim-Min, Liao Li-Fan, J. Org. Chem., 58 (1993) N 7, S 1754-1761

  摘要：

  DOI：

文献信息

• Regio-, stereo-, and enantioselectivity in the electrophilic reactions of 2-amino-4-phenyl-3-butenenitriles
  作者：Chih Jung Chang、Jim Min Fang、Li Fan Liao

  DOI：10.1021/jo00059a027

  日期：1993.3

  The allylic anion generated from 2-(N-methylanilino)-4-phenyl-3-butenenitrile (1) reacted with iodomethane and 3-bromo-1-chloropropane in THF/HMPA to give the gamma-substitution products exclusively, predominantly in the 2Z-configuration. Substitution of the N-methylanilino group with the methyl ether of L-(-)-ephedrine resulted in the generation of chiral aminonitrile 2. Lithiated 2 reacted sluggishly in THF with allyl bromide and benzyl chloride in the absence of HMPA to give the gamma-substitution products predominantly in the 2Z-configuration, with little diastereoselectivity. The aminonitrile 3 prepared from cinnamaldehyde, L-(-)-ephedrine, and KCN was lithiated with 2 equiv of LDA resulting in high facial selectivity (76-100% diastereomeric excess) in alkylations in the presence of HMPA and LiI. Lithiated 3 reacted with propionaldehyde, benzaldehyde, and p-bromobenzaldehyde at-78-degrees-C to give the gamma-addition products, predominantly in the 4R-configuration (64-78% de). The stereochemistry of the isomers of each product was determined by chemical correlation and spectral methods including analyses of the CD spectra and X-ray diffraction. A bicyclic transition state C wherein lithium is chelated by both amino and alkoxy groups is proposed to interpret the observed stereoselectivity.
• Chang Chih-Jung, Fang Jim-Min, Liao Li-Fan, J. Org. Chem., 58 (1993) N 7, S 1754-1761
  作者：Chang Chih-Jung, Fang Jim-Min, Liao Li-Fan

  DOI：——

  日期：——
• Conversion of α-Anilino Alkenenitriles to Amides by Chemoselective Palladium-Catalyzed Arylations
  作者：Chau-Chen Yang、Huo-Mu Tai、Pei-Jiun Sun

  DOI：10.1055/s-1997-5783

  日期：1997.7

  The reactions of α-anilino alkenenitriles with iodobenzene catalyzed by palladium gave amides and benzonitrile. A general mechanism is proposed to explain the chemoselective arylation at the cyano group.

  α-苯胺基烯烃腈与碘苯在钯催化下反应生成酰胺和苯甲腈。提出了一种通用机制来解释氰基的化学选择性芳基化。