4-methoxy-benzaldehyde phenanthro[9,10-e][1,2,4]triazin-3-ylhydrazone | 63484-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4-methoxy-benzaldehyde phenanthro[9,10-e][1,2,4]triazin-3-ylhydrazone
• 英文别名: N-[(4-methoxyphenyl)methylideneamino]phenanthro[9,10-e][1,2,4]triazin-3-amine
• CAS: 63484-70-8
• 化学式: C₂₃H₁₇N₅O
• 分子量: 379.421
• InChiKey: SMTCCEZKDULAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxy-benzaldehyde phenanthro[9,10-e][1,2,4]triazin-3-ylhydrazone 在 氯化亚砜 作用下， 反应 8.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis of Acyclo C-Nucleosides OF Phenanthro[9,10-e][1,2,4]Triazino[3,4-c]-[1,2,4] Triazoles, and Their Precursors

  摘要：

  Reaction of 3 -hydrazinophenanthro[9, 10-e][l,2,4]triazine (1) with aliphatic and aromatic aldehydes as well as monosaccharides gave the corresponding hydrazones 2a-g. The D-glucose analogue exists in the cyclic pyranosyl structure 5. Acetylation and partial acetylation of the sugar hydrazones were carried out. Cyclization of a number of hydrazones including the partially acetylated sugar hydrazones by thionyl chloride gave regioselectively the respective angular isomer 1-substituted phenanthro[9,10-e][ l,2,4]triazino[3,4-c][ 1,2,4]triazoles 16i-l, and not the linear isomer. The cyclization of 1 with acetic acid, however, gave regioselectively the linear isomer 19. The structural assignments were based on a model study whereby the angular 16a was found to be different from the linear isomer 19a obtained by the condensation of 4,5-diamino-3-methyl- 1,2,4-triazole with 9, 10-phenanthraquinone. Periodate oxidation of 2d gave 20 whose reaction with 1 gave 21.

  DOI：

  10.1080/07328319808003477
• 作为产物：
  描述：

  2H-phenanthro[9,10-e][1,2,4]triazine-3-thione 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-methoxy-benzaldehyde phenanthro[9,10-e][1,2,4]triazin-3-ylhydrazone
  参考文献：
  名称：

  Synthesis of Acyclo C-Nucleosides OF Phenanthro[9,10-e][1,2,4]Triazino[3,4-c]-[1,2,4] Triazoles, and Their Precursors

  摘要：

  Reaction of 3 -hydrazinophenanthro[9, 10-e][l,2,4]triazine (1) with aliphatic and aromatic aldehydes as well as monosaccharides gave the corresponding hydrazones 2a-g. The D-glucose analogue exists in the cyclic pyranosyl structure 5. Acetylation and partial acetylation of the sugar hydrazones were carried out. Cyclization of a number of hydrazones including the partially acetylated sugar hydrazones by thionyl chloride gave regioselectively the respective angular isomer 1-substituted phenanthro[9,10-e][ l,2,4]triazino[3,4-c][ 1,2,4]triazoles 16i-l, and not the linear isomer. The cyclization of 1 with acetic acid, however, gave regioselectively the linear isomer 19. The structural assignments were based on a model study whereby the angular 16a was found to be different from the linear isomer 19a obtained by the condensation of 4,5-diamino-3-methyl- 1,2,4-triazole with 9, 10-phenanthraquinone. Periodate oxidation of 2d gave 20 whose reaction with 1 gave 21.

  DOI：

  10.1080/07328319808003477

文献信息

• Synthesis of Acyclo C-Nucleosides OF Phenanthro[9,10-e][1,2,4]Triazino[3,4-c]-[1,2,4] Triazoles, and Their Precursors
  作者：Atef Hamed、Elham R. Abo-Amaym、El Sayed H. El Ashry

  DOI：10.1080/07328319808003477

  日期：1998.8

  Reaction of 3 -hydrazinophenanthro[9, 10-e][l,2,4]triazine (1) with aliphatic and aromatic aldehydes as well as monosaccharides gave the corresponding hydrazones 2a-g. The D-glucose analogue exists in the cyclic pyranosyl structure 5. Acetylation and partial acetylation of the sugar hydrazones were carried out. Cyclization of a number of hydrazones including the partially acetylated sugar hydrazones by thionyl chloride gave regioselectively the respective angular isomer 1-substituted phenanthro[9,10-e][ l,2,4]triazino[3,4-c][ 1,2,4]triazoles 16i-l, and not the linear isomer. The cyclization of 1 with acetic acid, however, gave regioselectively the linear isomer 19. The structural assignments were based on a model study whereby the angular 16a was found to be different from the linear isomer 19a obtained by the condensation of 4,5-diamino-3-methyl- 1,2,4-triazole with 9, 10-phenanthraquinone. Periodate oxidation of 2d gave 20 whose reaction with 1 gave 21.