1,3-diphenyl-1,4,5,6-tetrahydropyridazine | 24398-61-6

• 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: 1,3-diphenyl-1,4,5,6-tetrahydropyridazine
• 英文别名: 2,6-diphenyl-4,5-dihydro-3H-pyridazine
• CAS: 24398-61-6
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: IZRKAEFRTXCPIH-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  367.8±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-1,4,5,6-tetrahydropyridazine 以25%的产率得到
  参考文献：
  名称：

  SANNICOLO, F., TETRAHEDRON LETT., 1984, 25, N 29, 3101-3102

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenyl-1,4,5,6-tetrahydropyridazin-3(2H)-one 在 四(三苯基膦)钯 sodium carbonate 、 三氯氧磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.08h， 生成 1,3-diphenyl-1,4,5,6-tetrahydropyridazine
  参考文献：
  名称：

  Microwave-assisted cross-coupling of 3-chloro-2-pyrazolines and 3-chloro-1-phenyl-1,4,5,6-tetrahydropyridazine with aryl boronic acids

  摘要：

  3-Chloro-l-phenyl-2-pyrazoliiie and 3-chloo-1-phenyl-1,4,5,6-tetrahydropyridazine were coupled with aryl boronic acids in good yields under microwave heating conditions (140 degrees C, 5 min). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.075

文献信息

• Studies on the Fischer indole synthesis: Behaviour of cyclic hydrazones of tetrahydropyridazine and pyrazoline series in polyphosphoric acid.
  作者：Franco Sannicolò

  DOI：10.1016/0040-4039(84)80018-0

  日期：——

  Heating 1,3-diphenyl-1,4,5,6-tetrahydropyridazine in PPA affords mainly 4-benzoyl-1,2,3,4-tetrahydroquinoline and 2-anilinopropiophenone. In analogous conditions 1,5-diphenyl-3-methyl-2-pyrazoline gives 2-styrylindole, benzidine and benzylideneacetone.

  在PPA中加热1,3-二苯基-1,4,5,6-四氢哒嗪主要得到4-苯甲酰基-1,2,3,4-四氢喹啉和2-苯胺基苯乙酮。在类似条件下，1，5-二苯基-3-甲基-2-吡唑啉生成2-苯乙烯基吲哚，联苯胺和亚苄基丙酮。
• One-pot synthesis of 2,6-diaryl-4,5-dihydropyridazin-3(2H)-ones: Copper catalyzed annulation of aldehydes, arylhydrazines and 3-acryloyloxazolidin-2-one
  作者：Jianbo Zhao、Shengshu Lei、Min Wu、Can Pang、Hao Li

  DOI：10.1016/j.tetlet.2023.154473

  日期：2023.5

  The three-component synthesis of pyridazinones from aldehydes, arylhydrazines and 3-acryloyloxazolidin-2-one catalyzed by Cu(OTf)2 has been developed. This strategy exhibits high tolerance towards many functional groups including various aliphatic, aromatic and hetero-aromatic aldehydes to give 2,6-diaryl-4,5-dihydropyridazin-3(2H)-one products in moderate to high yields.

  开发了Cu(OTf) 2催化醛类、芳基肼类和3-丙烯酰恶唑烷-2-酮类三组分合成哒嗪酮类化合物。该策略对包括各种脂肪族、芳香族和杂芳族醛在内的许多官能团表现出高耐受性，以中高产率生成 2,6-diaryl-4,5-dihydropyridazin-3(2 H )-one 产物。
• Robinson, Brian; Khan, Munir I.; Shaw, Mark J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2265 - 2268
  作者：Robinson, Brian、Khan, Munir I.、Shaw, Mark J.

  DOI：——

  日期：——
• The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Yury V. Tomilov

  DOI：10.1016/j.tetlet.2014.09.017

  日期：2014.10

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.
• Schliemann; Buege; Reppel, Pharmazie, 1980, vol. 35, # 3, p. 140 - 143
  作者：Schliemann、Buege、Reppel

  DOI：——

  日期：——