2,6-二氰基-3-三氟甲基-5-甲基苯胺 | 507476-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,6-二氰基-3-三氟甲基-5-甲基苯胺
• 英文名称: 2,6-dicyano-3-trifluoromethyl-5-methylaniline
• 英文别名: 2-Amino-4-methyl-6-(trifluoromethyl)benzene-1,3-dicarbonitrile
• CAS: 507476-77-9
• 化学式: C₁₀H₆F₃N₃
• 分子量: 225.173
• InChiKey: UPIFYKLIYUXXAB-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  351.4±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-二氰基-3-三氟甲基-5-甲基苯胺 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以60%的产率得到2-iodo-4-methyl-6-(trifluoromethyl)isophthalonitrile
  参考文献：
  名称：

  Regioselective cyclization of unsymmetrical dicyanoanilines to novel 2,3-bifunctionalised indole regioisomers and their use in the synthesis of 4,5-dihydro[1,3]oxazino[5,4-b]indole-6-carbonitriles

  摘要：

  Synthesis of novel-2,3-bifunetionalised indole regioisomers (2/3 and 6/7) from unsymmetrical dicyanoanilines 1 by regioselective cyclization in two independent ways. Regioisomers 6 are further utilized in synthesis of novel 4,5-dihydro[1,3]oxazino[5,4-b] indole-6-carbonitriles 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.046
• 作为产物：
  描述：

  三氟乙酰丙酮 、 丙二腈 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到6-甲基-3-氰基-4-三氟甲基-2-羟基吡啶
  参考文献：
  名称：

  A simple and facile method for the synthesis of novel 5/7 trifluoromethyl-substituted 4(3H)-quinazolone regioisomers

  摘要：

  The unsymmetrical 1,3-diketones 1 on reaction with malononitrile is resulted an interesting trifunctional intermediates 2 and 3. The intermediate 2 is hydrolyzed to give 2,6-dicarboxamido aniline 4 which on cyclisation gave two regioisomers of 1,2-dihydro-4(3H)quinazolinones 5 and 6. The effect of substituents on compound 4 is characteristic for formation of regioisomers in different proportions. Each regioisomer on dehydrogenation under mild condition using active MnO2 gave corresponding 4(3H)-quinazolones 7 and 8, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00194-x

文献信息

• Regioselective addition of Grignard reagents to 2,6-dicyanoanilines and cyclization to new quinazoline derivatives under thermal/microwave irradiation conditions
  作者：D. Maitraie、T. Yakaiah、K. Srinivas、G. Venkat Reddy、S. Ravikanth、B. Narsaiah、P. Shanthan Rao、K. Ravikumar、B. Sridhar

  DOI：10.1016/j.jfluchem.2006.01.003

  日期：2006.3

  with Grignard reagents gave imine regioisomers 4 and 5. Each imine regioisomer was separated and independently cyclized to give new quinazoline derivatives 6, 7 and 8, 9, respectively, under different microwave irradiation conditions.

  已经开发了两种合成新的喹唑啉衍生物的策略。2，6-二氰基苯胺与格氏试剂反应，然后环化，得到两个喹唑啉区域异构体2和3。交替地，与格氏试剂反应的2，6-二氰基苯胺产生亚胺区域异构体4和5。各区域异构体亚胺分离并独立地环化，得到新的喹唑啉衍生物6，7和8，9分别不同的微波照射的条件下。
• A simple and facile method for the synthesis of novel 5/7 trifluoromethyl-substituted 4(3H)-quinazolone regioisomers
  作者：D. Maitraie、G. Venkat Reddy、V.V.V.N.S. Rama Rao、S. Ravi Kanth、P. Shanthan Rao、B. Narsaiah

  DOI：10.1016/s0022-1139(02)00194-x

  日期：2002.12

  The unsymmetrical 1,3-diketones 1 on reaction with malononitrile is resulted an interesting trifunctional intermediates 2 and 3. The intermediate 2 is hydrolyzed to give 2,6-dicarboxamido aniline 4 which on cyclisation gave two regioisomers of 1,2-dihydro-4(3H)quinazolinones 5 and 6. The effect of substituents on compound 4 is characteristic for formation of regioisomers in different proportions. Each regioisomer on dehydrogenation under mild condition using active MnO2 gave corresponding 4(3H)-quinazolones 7 and 8, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.
• Regioselective cyclization of unsymmetrical dicyanoanilines to novel 2,3-bifunctionalised indole regioisomers and their use in the synthesis of 4,5-dihydro[1,3]oxazino[5,4-b]indole-6-carbonitriles
  作者：D. Maitraie、G. Venkat Reddy、V.V.V.N.S. Rama Rao、S. Ravikanth、B. Narsaiah、P. Shanthan Rao、K. Ravikumar、B. Sridhar

  DOI：10.1016/j.tet.2005.02.046

  日期：2005.4

  Synthesis of novel-2,3-bifunetionalised indole regioisomers (2/3 and 6/7) from unsymmetrical dicyanoanilines 1 by regioselective cyclization in two independent ways. Regioisomers 6 are further utilized in synthesis of novel 4,5-dihydro[1,3]oxazino[5,4-b] indole-6-carbonitriles 9. (c) 2005 Elsevier Ltd. All rights reserved.