N1-(2-chlorophenyl)-N1-methylbenzene-1,2-diamine | 1207629-88-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N1-(2-chlorophenyl)-N1-methylbenzene-1,2-diamine
• 英文别名: N¹-(2-chlorophenyl)-N¹-methylbenzene-1,2-diamine；2-N-(2-chlorophenyl)-2-N-methylbenzene-1,2-diamine
• CAS: 1207629-88-6
• 化学式: C₁₃H₁₃ClN₂
• 分子量: 232.713
• InChiKey: HUKCVIIOYCXPFT-UHFFFAOYSA-N

物化性质

• 沸点：
  366.6±27.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2921590090

反应信息

• 作为反应物：
  描述：

  N1-(2-chlorophenyl)-N1-methylbenzene-1,2-diamine 在 钾硼氢 、 potassium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(l) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 N-methyl-2-(10-methylphenazin-5(10H)-yl)aniline
  参考文献：
  名称：

  Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

  摘要：

  Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.

  DOI：

  10.1021/jo302795w
• 作为产物：
  描述：

  (2'-氯苯基)-(2-硝基苯基)-胺 在 钾硼氢 、 copper(l) chloride 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 N1-(2-chlorophenyl)-N1-methylbenzene-1,2-diamine
  参考文献：
  名称：

  Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

  摘要：

  Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.

  DOI：

  10.1021/jo302795w

文献信息

• Supramolecular Scaffolds and Methods of Making the Same
  申请人：Becker Daniel P.

  公开号：US20100041880A1

  公开（公告）日：2010-02-18

  Tribenzo-1,4,7-triazacyclononane and derivatives thereof having a formula (I) are disclosed. Methods of making tribenzo-1,4,7-triazacyclononane and related compounds also are disclosed.

  Tribenzo-1,4,7-triazacyclononane及其衍生物的化学式（I）已被披露。同时也披露了制备Tribenzo-1,4,7-triazacyclononane和相关化合物的方法。
• Supramolecular scaffolds and methods of making the same
  申请人：Loyola University of Chicago

  公开号：US08173803B2

  公开（公告）日：2012-05-08

  Tribenzo-1,4,7-triazacyclononane and derivatives thereof having a formula (I) are disclosed. Methods of making tribenzo-1,4,7-triazacyclononane and related compounds also are disclosed.

  本文披露了具有公式(I)的Tribenzo-1,4,7-三氮杂环壬烷及其衍生物。还披露了制备Tribenzo-1,4,7-三氮杂环壬烷和相关化合物的方法。
• Synthesis of an <i>ortho</i>-Triazacyclophane: <i>N</i>,<i>N</i>′,<i>N</i>′′-Trimethyltribenzo-1,4,7-triazacyclononatriene
  作者：Andria M. Panagopoulos、Matthias Zeller、Daniel P. Becker

  DOI：10.1021/jo1017074

  日期：2010.11.19

  N,N',N ''-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield An X-ray crystal structure shows the new cyclophane to have a C-2-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV)
• US8173803B2
  申请人：——

  公开号：US8173803B2

  公开（公告）日：2012-05-08
• Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate
  作者：Andria M. Panagopoulos、Doug Steinman、Alexandra Goncharenko、Kyle Geary、Carlene Schleisman、Elizabeth Spaargaren、Matthias Zeller、Daniel P. Becker

  DOI：10.1021/jo302795w

  日期：2013.4.19

  Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.