N,N-Dibutyl-3-cyanomethyl-benzamide | 208921-81-7

• 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: N,N-Dibutyl-3-cyanomethyl-benzamide
• 英文别名: N,N-dibutyl-3-(cyanomethyl)benzamide
• CAS: 208921-81-7
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: UFFYOWIFDZXXCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-Dibutyl-3-cyanomethyl-benzamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到N,N-Dibutyl-3-cyanomethyl-thiobenzamide
  参考文献：
  名称：

  From donor and acceptor substitutedmeta- andpara-xylenes topara-Quinodimethanes and Poly(meta-phenylenevinylene)s

  摘要：

  Ortho-, meta-and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the alpha- and alpha' positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene] ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(metaphenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.

  DOI：

  10.1002/prac.19983400412
• 作为产物：
  描述：

  3-氰甲基苯甲酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 N,N-Dibutyl-3-cyanomethyl-benzamide
  参考文献：
  名称：

  From donor and acceptor substitutedmeta- andpara-xylenes topara-Quinodimethanes and Poly(meta-phenylenevinylene)s

  摘要：

  Ortho-, meta-and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the alpha- and alpha' positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene] ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(metaphenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.

  DOI：

  10.1002/prac.19983400412

文献信息

• From donor and acceptor substitutedmeta- andpara-xylenes topara-Quinodimethanes and Poly(meta-phenylenevinylene)s
  作者：Carsten Former、Gerrit Kl�rner、Manfred Wagner、Klaus M�llen

  DOI：10.1002/prac.19983400412

  日期：——

  Ortho-, meta-and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the alpha- and alpha' positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene] ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(metaphenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.