2-(2-cyanoethenyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine | 652138-58-4

• 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: 2-(2-cyanoethenyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine
• 英文别名: 3-[2,5-Bis(dimethylamino)phenyl]prop-2-enenitrile；3-[2,5-bis(dimethylamino)phenyl]prop-2-enenitrile
• CAS: 652138-58-4
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: RVLURLKDKAAVES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-cyanoethenyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以67%的产率得到2-(2-cyanoethyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine
  参考文献：
  名称：

  Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor

  摘要：

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.

  DOI：

  10.1021/jo035409w
• 作为产物：
  描述：

  丙烯腈 、 2-iodo-N,N,N',N'-tetramethyl-1,4-benzenediamine 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以72%的产率得到2-(2-cyanoethenyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine
  参考文献：
  名称：

  Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor

  摘要：

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.

  DOI：

  10.1021/jo035409w

文献信息

• Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor
  作者：Lyle D. Wescott、Daniell Lewis Mattern

  DOI：10.1021/jo035409w

  日期：2003.12.1

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.