N-(4-bromophenylmethylidene)quinolin-5-amine | 162854-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(4-bromophenylmethylidene)quinolin-5-amine
• 英文别名: 1-(4-bromophenyl)-N-quinolin-5-ylmethanimine
• CAS: 162854-67-3
• 化学式: C₁₆H₁₁BrN₂
• 分子量: 311.181
• InChiKey: TYNSIKRETYVQGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.25
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenylmethylidene)quinolin-5-amine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 苯 为溶剂， 以84%的产率得到N-(4-bromobenzyl)quinolin-5-amine
  参考文献：
  名称：

  Reductive transformations of Schiff bases in the synthesis of functionally substituted heteroaromatic amines

  摘要：

  Schiff bases synthesized by condensation of 5- and 6-aminoquinolines, 5-amino-2-methylquinoline, nitroanilines, and pyrimidinylaminoanilines with substituted benzaldehydes and pyridinecarbaldehydes were reduced with sodium tetrahydridoborate in acetic acid to obtain the corresponding N-aryl(hetaryl)benzylamines, N-(pyridylmethyl)anilines, and N-(1,2,3,4-tetrahydroquinolyl)benzylamine derivatives. The reduction of arylhetarylimines with hydrazine hydrate in the presence of Raney nickel involved only the azomethine C=N bond, while the nitrogen-containing heteroaromatic ring remained intact. Under analogous conditions, nitrosubstituted Schiff bases and benzyl- and pyridylmethylamines were converted into previously unknown N-(aminobenzyl)quinolinamines and aryl(pyridyl)methyl-substituted phenylenediamines.

  DOI：

  10.1134/s1070428009070148
• 作为产物：
  描述：

  5-氨基喹啉 、 对溴苯甲醛 以 乙醇 为溶剂， 以85%的产率得到N-(4-bromophenylmethylidene)quinolin-5-amine
  参考文献：
  名称：

  Reductive transformations of Schiff bases in the synthesis of functionally substituted heteroaromatic amines

  摘要：

  Schiff bases synthesized by condensation of 5- and 6-aminoquinolines, 5-amino-2-methylquinoline, nitroanilines, and pyrimidinylaminoanilines with substituted benzaldehydes and pyridinecarbaldehydes were reduced with sodium tetrahydridoborate in acetic acid to obtain the corresponding N-aryl(hetaryl)benzylamines, N-(pyridylmethyl)anilines, and N-(1,2,3,4-tetrahydroquinolyl)benzylamine derivatives. The reduction of arylhetarylimines with hydrazine hydrate in the presence of Raney nickel involved only the azomethine C=N bond, while the nitrogen-containing heteroaromatic ring remained intact. Under analogous conditions, nitrosubstituted Schiff bases and benzyl- and pyridylmethylamines were converted into previously unknown N-(aminobenzyl)quinolinamines and aryl(pyridyl)methyl-substituted phenylenediamines.

  DOI：

  10.1134/s1070428009070148

文献信息

• Reductive transformations of Schiff bases in the synthesis of functionally substituted heteroaromatic amines
  作者：Zh. V. Ignatovich、A. P. Kadutskii、E. V. Koroleva、A. V. Baranovskii、K. N. Gusak

  DOI：10.1134/s1070428009070148

  日期：2009.7

  Schiff bases synthesized by condensation of 5- and 6-aminoquinolines, 5-amino-2-methylquinoline, nitroanilines, and pyrimidinylaminoanilines with substituted benzaldehydes and pyridinecarbaldehydes were reduced with sodium tetrahydridoborate in acetic acid to obtain the corresponding N-aryl(hetaryl)benzylamines, N-(pyridylmethyl)anilines, and N-(1,2,3,4-tetrahydroquinolyl)benzylamine derivatives. The reduction of arylhetarylimines with hydrazine hydrate in the presence of Raney nickel involved only the azomethine C=N bond, while the nitrogen-containing heteroaromatic ring remained intact. Under analogous conditions, nitrosubstituted Schiff bases and benzyl- and pyridylmethylamines were converted into previously unknown N-(aminobenzyl)quinolinamines and aryl(pyridyl)methyl-substituted phenylenediamines.