N'-(2-cyanophenyl)-N,N-dimethylacetamidine | 102669-53-4

• 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: N'-(2-cyanophenyl)-N,N-dimethylacetamidine
• 英文别名: N'-(2-cyanophenyl)-N,N-dimethylethanimidamide
• CAS: 102669-53-4
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD00994886
• 分子量: 187.244
• InChiKey: UGVKZWBSLDLRJO-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  323.1±44.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-(2-cyanophenyl)-N,N-dimethylacetamidine 、 N-甲基-P-氨基苯甲醚 在 aluminum (III) chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 以71%的产率得到(4-甲氧基苯基)(甲基)(2-甲基喹唑啉-4-基)胺
  参考文献：
  名称：

  Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent

  摘要：

  A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to AZiXa (TM) (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.066
• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 N'-(2-氰基苯基)-N,N-二甲基甲脒 反应 0.03h， 以88%的产率得到N'-(2-cyanophenyl)-N,N-dimethylacetamidine
  参考文献：
  名称：

  Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent

  摘要：

  A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to AZiXa (TM) (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.066

文献信息

• [EN] IMINOTHIADIAZINE DIOXIDE COMPOUNDS AS BACE INHIBITORS, COMPOSITIONS, AND THEIR USE<br/>[FR] COMPOSÉS DE DIOXYDE D'IMINOTHIADIAZINE COMME INHIBITEURS DE BACE, COMPOSITIONS ET LEUR UTILISATION
  申请人：SCHERING CORP

  公开号：WO2011044181A1

  公开（公告）日：2011-04-14

  In its many embodiments, the present invention provides certain iminothiadiazine dioxide compounds, including compounds Formula (I): (I) and include stereoisomers thereof, and pharmaceutically acceptable salts of said compounds stereoisomers, wherein each of R1, R2, R3, R4, R5, R9, ring A, ring B, m, n, p, -L1-,L2-, and L3- is selected independently and as defined herein. The novel iminothiadiazine dioxide compounds of the invention have surprisingly been found to exhibit properties which are expected to render them advantageous as BACE inhibitors and/or for the treatment and prevention of various pathologies related to β-amyloid (Aβ) production. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use in treating pathologies associated with amyloid beta (Aβ) protein, including Alzheimers disease, are also disclosed.

  在其多种实施方式中，本发明提供了某些亚氨基噻二嗪二氧化物化合物，包括化合物式(I)的化合物和其立体异构体，以及所述化合物立体异构体的药学上可接受的盐，其中每个R1、R2、R3、R4、R5、R9、环A、环B、m、n、p、-L1-、L2-和L3-都是独立选择并在此定义。该发明的新型亚氨基噻二嗪二氧化物化合物出人意料地表现出具有优势的BACE抑制剂特性和/或用于治疗和预防与β-淀粉样蛋白（Aβ）产生相关的各种病理的特性。还公开了包括一种或多种这样的化合物（单独和与一种或多种其他活性剂的组合）的制药组合物，并揭示了在治疗与淀粉样β（Aβ）蛋白相关的病理，包括阿尔茨海默病中使用它们的方法。
• Tetrahedron, 2010, 66, 4495-4502
  作者：

  DOI：——

  日期：——
• Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent
  作者：Alicia Foucourt、Carole Dubouilh-Benard、Elizabeth Chosson、Cécile Corbière、Catherine Buquet、Mauro Iannelli、Bertrand Leblond、Francis Marsais、Thierry Besson

  DOI：10.1016/j.tet.2010.04.066

  日期：2010.6

  A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to AZiXa (TM) (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. (C) 2010 Elsevier Ltd. All rights reserved.