6-<(4-Chlorophenyl)amino>-2,4-dimethyl-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione | 152897-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-<(4-Chlorophenyl)amino>-2,4-dimethyl-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione
• 英文别名: 9-(4-chloroanilino)-4,6-dimethyl-4,6,8,10,11-pentazatetracyclo[8.8.0.02,7.013,18]octadeca-2(7),8,11,13,15,17-hexaene-3,5-dione
• CAS: 152897-86-4
• 化学式: C₂₁H₁₇ClN₆O₂
• 分子量: 420.858
• InChiKey: PHZRTADPKZGTKD-UHFFFAOYSA-N

物化性质

• 沸点：
  562.8±60.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.99
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-<(4-Chlorophenyl)amino>-2,4-dimethyl-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione 在 potassium permanganate 作用下， 以 水 为溶剂， 反应 5.0h， 以33%的产率得到6-<(4-Chlorophenyl)imino>-2,4-dimethylpyrimido<4',5':4,5>pyrimido<6,1-a>phthalazine-1,3(2H,4H)-dione
  参考文献：
  名称：

  Reactions of uracils. 21. Zwitterionic heteropolycyclic uracils by a novel three-component reaction: iminophosphorane, isocyanate, heteroarene

  摘要：

  The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.

  DOI：

  10.1021/jo00077a013
• 作为产物：
  描述：

  2,3-二氮杂萘 、 1,3-dimethyl-2,4-dioxo-6[(triphenylphosphoranylidene)-amino]-1,2,3,4-tetrahydropyrimidine 、 对氯苯异氰酸酯 以 乙腈 为溶剂， 以95%的产率得到6-<(4-Chlorophenyl)amino>-2,4-dimethyl-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione
  参考文献：
  名称：

  Reactions of uracils. 21. Zwitterionic heteropolycyclic uracils by a novel three-component reaction: iminophosphorane, isocyanate, heteroarene

  摘要：

  The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.

  DOI：

  10.1021/jo00077a013

文献信息

• Wamhoff Heinrich, Schmidt Andreas, J. Org. Chem., 58 (1993) N 25, S 6976-6984
  作者：Wamhoff Heinrich, Schmidt Andreas

  DOI：——

  日期：——