3,4-dichloro-6-<(trimethylsilyl)oxy>pyridazine | 87009-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,4-dichloro-6-<(trimethylsilyl)oxy>pyridazine
• 英文别名: 3,4-dichloro-6-[(trimethylsilyl)oxy]pyridazine；(5,6-Dichloropyridazin-3-yl)oxy-trimethylsilane
• CAS: 87009-00-5
• 化学式: C₇H₁₀Cl₂N₂OSi
• 分子量: 237.161
• InChiKey: OCPHYKQYPHYIDO-UHFFFAOYSA-N

物化性质

• 沸点：
  264.6±40.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 3,4-dichloro-6-<(trimethylsilyl)oxy>pyridazine 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.75h， 以92%的产率得到3,4-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyridazin-6-one
  参考文献：
  名称：

  Katz, David J.; Wise, Dean S.; Townsend, Leroy B., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 369 - 379

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二氯哒嗪-3(2H)-酮 、 N,N-二(三甲基硅基)乙酰胺 以 乙腈 为溶剂， 反应 1.0h， 生成 3,4-dichloro-6-<(trimethylsilyl)oxy>pyridazine
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents

  摘要：

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

  DOI：

  10.1080/15257779408013255

文献信息

• Katz, David J.; Wise, Dean S.; Townsend, Leroy B., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 369 - 379
  作者：Katz, David J.、Wise, Dean S.、Townsend, Leroy B.

  DOI：——

  日期：——
• Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents
  作者：Biserka Kasnar、Dean S. Wise、Louis S. Kucera、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257779408013255

  日期：1994.3

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.