1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine | 1427303-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine
• 英文别名: 2,3-dimethyl-2-(2-nitrophenyl)-1H-perimidine
• CAS: 1427303-51-2
• 化学式: C₁₉H₁₇N₃O₂
• 分子量: 319.363
• InChiKey: YXOBSFRQTVLCQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到N-methyl-8-(3-methyl-2H-indazol-2-yl)naphthalen-1-amine
  参考文献：
  名称：

  Visible light-sensitive properties of 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine

  摘要：

  Four o- and p-nitro substituted 2-methyl-2-phenyl-2,3-dihydro-1H-perimidine derivatives were synthesized via a condensation cyclization of naphthalene-1,8-diamine with nitro substituted acetophenones to study their photochemical properties. Only the o-nitrophenyl substituted perimidine 1 was found to be sensitive to light. When exposed to visible light under either aerobic conditions or argon atmosphere, it undergoes pyrimidine ring-opening/deoxygenation and pyrimidine oxidation to give the 2H-indazole 10 and perimidinone 11, respectively. A new visible light-sensitive o-nitrobenzylamino scaffold is introduced. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.079
• 作为产物：
  描述：

  邻硝基苯乙酮 在 三乙胺 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 85.0h， 生成 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine
  参考文献：
  名称：

  Visible light-sensitive properties of 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine

  摘要：

  Four o- and p-nitro substituted 2-methyl-2-phenyl-2,3-dihydro-1H-perimidine derivatives were synthesized via a condensation cyclization of naphthalene-1,8-diamine with nitro substituted acetophenones to study their photochemical properties. Only the o-nitrophenyl substituted perimidine 1 was found to be sensitive to light. When exposed to visible light under either aerobic conditions or argon atmosphere, it undergoes pyrimidine ring-opening/deoxygenation and pyrimidine oxidation to give the 2H-indazole 10 and perimidinone 11, respectively. A new visible light-sensitive o-nitrobenzylamino scaffold is introduced. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.079

文献信息

• Visible light-sensitive properties of 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine
  作者：Wei-Zhe Chen、Hao-Yi Wei、Ding-Yah Yang

  DOI：10.1016/j.tet.2013.01.079

  日期：2013.4

  Four o- and p-nitro substituted 2-methyl-2-phenyl-2,3-dihydro-1H-perimidine derivatives were synthesized via a condensation cyclization of naphthalene-1,8-diamine with nitro substituted acetophenones to study their photochemical properties. Only the o-nitrophenyl substituted perimidine 1 was found to be sensitive to light. When exposed to visible light under either aerobic conditions or argon atmosphere, it undergoes pyrimidine ring-opening/deoxygenation and pyrimidine oxidation to give the 2H-indazole 10 and perimidinone 11, respectively. A new visible light-sensitive o-nitrobenzylamino scaffold is introduced. (C) 2013 Elsevier Ltd. All rights reserved.