2-(3-aminopropyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine | 852695-06-8

• 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-(3-aminopropyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine
• 英文别名: 3-tetramethylphenylenediaminylpropylamime；2-(3-aminopropyl)-1-N,1-N,4-N,4-N-tetramethylbenzene-1,4-diamine
• CAS: 852695-06-8
• 化学式: C₁₃H₂₃N₃
• 分子量: 221.346
• InChiKey: XKYGXDQIOUZTIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(10-nonadecyl)-3,4,9,10-perylenetetracarboxylic acid 3,4-anhydride-9,10-imide 、 2-(3-aminopropyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine 以 甲苯 为溶剂， 反应 4.0h， 以80%的产率得到N-(9-nonadecyl)-N'-(3-[2-(N'',N'',N''',N'''-tetramethyl-1,4-benzenediaminyl)propyl])perylene-4,5,9,10-bis(dicarboximide)
  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：

  2-(2-cyanoethenyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.33h， 生成 2-(3-aminopropyl)-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

• Synthesis of Donor-σ-Perylenebisimide-Acceptor Molecules Having PEG Swallowtails and Sulfur Anchors
  作者：Rajesh Kota、Ramakrishna Samudrala、Daniell Lewis Mattern

  DOI：10.1021/jo301701a

  日期：2012.11.2

  poly(ethylene glycol) (PEG) swallowtails with 6 ether oxygens or with 4 ether oxygens to promote hydrophilicity in orienting LB monolayers, and alkyl swallowtails ending with sulfur anchors (thioacetate, thiol, or methyl disulfide) to stabilize attachment of the D-σ-A molecules to gold electrodes. The preparation and characterization of D-σ-A molecules containing combinations of these swallowtails with pyrene

  排列在电极之间单层中的施主-σ-受体（D-σ-A）分子可用作分子整流器。使用per 3,4,9,10-四羧酸双酰亚胺（PBI）作为受体可使施主基团与一个酰亚胺氮和可溶的燕尾连接，通常较长（例如，C 19）烷烃连接在中链，另一端。这样的烷基尾促进了Langmuir-Blodgett（LB）单层的形成。我们已经使用了几种改良的燕尾来制造新的D-σ-A分子：具有6个醚氧或具有4个醚氧的聚（乙二醇）（PEG）燕尾以增强定向LB单层的亲水性，以及以硫锚定结尾的烷基燕尾（硫代乙酸盐，硫醇或二硫化甲基）来稳定D-σ-A分子与金电极的附着。描述了包含这些燕尾与pyr，二茂铁和四甲基苯二胺供体基团的组合的D-σ-A分子的制备和表征。
• 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.