dicyano(2,2-dimethyl-3-(4-methyl-benzoyl)-5-p-tolyl-1-aza-cyclopenta-3,5-dien-1-ium-1-yl)methanide | 244228-83-9

• 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: dicyano(2,2-dimethyl-3-(4-methyl-benzoyl)-5-p-tolyl-1-aza-cyclopenta-3,5-dien-1-ium-1-yl)methanide
• 英文别名: [2-Cyano-2-[2,2-dimethyl-3-(4-methylbenzoyl)-5-(4-methylphenyl)pyrrol-1-ium-1-yl]ethenylidene]azanide
• CAS: 244228-83-9
• 化学式: C₂₄H₂₁N₃O
• 分子量: 367.45
• InChiKey: DMJRFJGXURFFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-二乙氧基乙烯 、 dicyano(2,2-dimethyl-3-(4-methyl-benzoyl)-5-p-tolyl-1-aza-cyclopenta-3,5-dien-1-ium-1-yl)methanide 以 乙腈 为溶剂， 反应 96.0h， 以56%的产率得到2,2-bis-ethoxy-5,5-dimethyl-6-(4-methylbenzoyl)-7a-p-tolyl-1,2,5,7a-tetrahydropyrrolizine-3,3-dicarbonitrile
  参考文献：
  名称：

  1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Preparative Aspects

  摘要：

  Stable bicyclic, monocyclic and aromatic azomethine ylides 1, 13 and 16 add angle-strained, electron-rich and electron-poor alkynes as well as alkenes and heterocumulenes to form 1:1-adducts in highly stereoselective 1,3-dipolar cycloadditions. Unsymmetrical dipalarophiles react in a regiospecific manner. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00453-1
• 作为产物：
  描述：

  7,7-dimethyl-2,5-bis(p-tolyl)-3,4-diazanorcaradiene 在 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 dicyano(2,2-dimethyl-3-(4-methyl-benzoyl)-5-p-tolyl-1-aza-cyclopenta-3,5-dien-1-ium-1-yl)methanide
  参考文献：
  名称：

  3,4-二氮杂茂铁和4,5-二氢哒嗪为新型稳定的偶氮甲亚胺的前体

  摘要：

  报道了由3，4-二氮杂正丁烯衍生物衍生的新型的稳定的有色甲亚胺基化物3的合成，其在酸催化下被转化为含有五元的1-氮杂-1，3-环戊二烯骨架的有色的稳定的甲亚胺基化物4。。甲亚胺叶立德3在沸腾甲醇中重排以3,5- diazahomotropilidenes 8以良好的收率。

  DOI：

  10.1016/s0040-4020(99)00516-5

文献信息

• Nonstereospecific 1,3-dipolar cycloadditions of azomethine ylides and enamines
  作者：Thomas Böhm、Andreas Weber、Jürgen Sauer

  DOI：10.1016/s0040-4020(99)00517-7

  日期：1999.7

  The combination of electron-poor azomethine ylides 3 (AMY-I) or 4 (AMY-II) with electron-rich enamines 5 results in nonstereospecific 1,3-dipolar cycloadditions, which are LUMOdipole-HOMOdipolarophile controlled reactions. This phenomenon can be explained only by a two-step mechanism via zwitterionic intermediates.

  贫电子甲亚胺叶立德的组合3（AMY-I）或4（AMY-II）与富电子烯胺5周的结果在nonstereospecific 1,3-偶极环加成，其LUMO偶极-HOMO亲偶极控制的反应。这种现象只能通过两性离子中间体的两步机理来解释。
• Nonstereospecific 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides: Proof of the Structures for Four Diastereoisomeric [3+2] Cycloadducts
  作者：J. Breu、K.-J. Range、A. Weber、J. Sauer

  DOI：10.1107/s010827019701439x

  日期：1998.4.15

  Racemic azomethine ylides [(I) or (IV)] have been found to undergo cycloaddition to a trans-enamine [(II)] in a nonstereospecific way to yield mixtures of racemic diastereoisomeric 1:1 adducts: 5-dimethylamino-1,1,6-trimethyl-2,6a-di-p-tolyl-1,1a,5,6,6a,6b-hexahydro-4H-3,3a-diazacyclopropa[e]indene-4,4-dicarbonitrile, C-29-H33N5 [(IIIa) and (IIIb)], or 2-dimethylamino-1,5,5-trimethyl-6-(4-methylbenzoyl)-7a-p-tolyl-2,3,5,7a-tetrahydro-1H-pyrrolizine-3,3-dicarbonitrile (pyrrolizine is pyrrolo[1,2-a]pyrrole), C29H32N4O [(Va) and (Vb)]. Crystal structure analyses prove the structures and configurations for the three diastereoisomeric adducts (ma), (IIIb) and (Vb) unequivocally. In all three cases, the dimethylamino group is endo to the five-membered ring formed in the cycloaddition step. In (cis-1a-cis-4a-transoid-8a,8b-transoid-8b,8c)-1,1-dimethyl-4a-(pyrrolidin-1-yl)-2,8b-di-p-tolyl-1,1a,4a,5,6,7,8,8a,8b,8c-decahydro-4H-3 ,3a-diazacyclopropa[c]fluorene-4,4-dicarbonitrile, C34H39N5, (VII), the cycloadduct formed using an azomethine ylide [(I)] and a cyclic enamine [(VI)], the amino function is again found in an endo position.
• Nonstereospecific 1,3-dipolar cycloadditions — LUMODipole-HOMODipolarophile controlled reactions
  作者：Andreas Weber、Jürgen Sauer

  DOI：10.1016/s0040-4039(97)10762-6

  日期：1998.2

  FMO-theory predicts a two-step mechanism accompanied by nonstereospecificity for 1,3-dipolar cycloadditons if one HOMO-LUMO interaction dominates the other one. R. Huisgen proved this phenomenon for the combination of electron-rich thiocarbonyl ylides with electron-poor dipolarophiles. For the first time we report on nonstereospecific reactions of electron-poor 1,3-dipoles 1 and 5 with the electron-rich trans-enamine 2. (C) 1998 Elsevier Science Ltd. All rights reserved.