(Z)-7-chloro-2-(N-methylanilino)-4-phenyl-2-heptenenitrile | 120568-30-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-7-chloro-2-(N-methylanilino)-4-phenyl-2-heptenenitrile
• 英文别名: (Z)-7-chloro-2-(N-methylanilino)-4-phenylhept-2-enenitrile
• CAS: 120568-30-1
• 化学式: C₂₀H₂₁ClN₂
• 分子量: 324.853
• InChiKey: GPFZTUZXAFFGAL-HKWRFOASSA-N

物化性质

• 沸点：
  500.8±50.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-chloro-2-(N-methylanilino)-4-phenyl-2-heptenenitrile 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  α-苯胺基烯腈的分子内自由基环化

  摘要：

  用三丁基锡烷处理后，在适当位置具有卤素取代基的2-苯胺基2-烯腈进行自由基环化，以立体选择的方式得到环烷基α-氨基腈。

  DOI：

  10.1039/c39880001385
• 作为产物：
  描述：

  (E)-2-(methyl(phenyl)amino)-4-phenylbut-3-enenitrile 、 1-溴-3-氯丙烷 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 (Z)-7-chloro-2-(N-methylanilino)-4-phenyl-2-heptenenitrile
  参考文献：
  名称：

  Regio-, stereo-, and enantioselectivity in the electrophilic reactions of 2-amino-4-phenyl-3-butenenitriles

  摘要：

  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.

  DOI：

  10.1021/jo00059a027

文献信息

• FANG, JIM-MIN;CHANG, HAN-TING;LIN, CHUN-CHENG, J. CHEM. SOC. CHEM. COMMUN.,(1988) N0, C. 1385-1386
  作者：FANG, JIM-MIN、CHANG, HAN-TING、LIN, CHUN-CHENG

  DOI：——

  日期：——
• 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：——