(E,Z)-α-<3-(Dimethylamino)-2-propenylidene>-3-(trifluoromethyl)benzeneacetonitrile | 163562-98-9

• 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,Z)-α-<3-(Dimethylamino)-2-propenylidene>-3-(trifluoromethyl)benzeneacetonitrile
• 英文别名: (2Z,4E)-5-(dimethylamino)-2-[3-(trifluoromethyl)phenyl]penta-2,4-dienenitrile
• CAS: 163562-98-9
• 化学式: C₁₄H₁₃F₃N₂
• 分子量: 266.266
• InChiKey: RQZGTXYKCXRAOX-QJQVOESFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,Z)-α-<3-(Dimethylamino)-2-propenylidene>-3-(trifluoromethyl)benzeneacetonitrile 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 以65%的产率得到3-<3-(Trifluoromethyl)phenyl>-2-chloropyridine
  参考文献：
  名称：

  New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines

  摘要：

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.

  DOI：

  10.1021/jo00117a029
• 作为产物：
  描述：

  Bredereck 试剂 、 (Z)-2-[3-(trifluoromethyl)phenyl]but-2-enenitrile 以 四氢呋喃 为溶剂， 反应 20.0h， 以66%的产率得到(E,Z)-α-<3-(Dimethylamino)-2-propenylidene>-3-(trifluoromethyl)benzeneacetonitrile
  参考文献：
  名称：

  New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines

  摘要：

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.

  DOI：

  10.1021/jo00117a029

文献信息

• New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines
  作者：Robert Church、Ronald Trust、J. Donald Albright、Dennis Powell

  DOI：10.1021/jo00117a029

  日期：1995.6

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.