Methanesulfonic acid 10-cyano-4-ethyl-3-methyl-10,11-dihydro-5-thia-2,11-diaza-dibenzo[a,d]cyclohepten-1-yl ester | 852158-04-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methanesulfonic acid 10-cyano-4-ethyl-3-methyl-10,11-dihydro-5-thia-2,11-diaza-dibenzo[a,d]cyclohepten-1-yl ester
• CAS: 852158-04-4
• 化学式: C₁₇H₁₇N₃O₃S₂
• 分子量: 375.472
• InChiKey: CPEOQKARNJPLAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 10-cyano-4-ethyl-3-methyl-10,11-dihydro-5-thia-2,11-diaza-dibenzo[a,d]cyclohepten-1-yl ester 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以72%的产率得到4-ethyl-3-methyl-1-oxo-10,11-dihydro-2H-pyrido[4,3-b]benzo[f][1,4]thiazepin-10-yl carbonitrile
  参考文献：
  名称：

  Tosylation/mesylation of 4-hydroxy-3-nitro-2-pyridinones as an activation step in the construction of dihydropyrido[3,4-b] benzo[f][1,4]thiazepin-1-one based anti-HIV agents

  摘要：

  Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16. Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78% yield. This compound was efficiently converted to the target tricyclic products 4a and b. Compound 4a, in particular, is a potent inhibitor in vitro (IC50 = 2 nM) of wild type HIV-1 replication. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.128
• 作为产物：
  描述：

  2-(tert-butyl-dimethylsilanoxymethyl)benzenethiol 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 sodium thiosulfate 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 22.83h， 生成 Methanesulfonic acid 10-cyano-4-ethyl-3-methyl-10,11-dihydro-5-thia-2,11-diaza-dibenzo[a,d]cyclohepten-1-yl ester
  参考文献：
  名称：

  Tosylation/mesylation of 4-hydroxy-3-nitro-2-pyridinones as an activation step in the construction of dihydropyrido[3,4-b] benzo[f][1,4]thiazepin-1-one based anti-HIV agents

  摘要：

  Reaction of 4-hydroxy-3-nitropyridinone 8 with TsCl and MsCl, respectively, resulted in rapid and quantitative formation of ditosylate 13 and dimesylate 16. Through chemoselective reaction of 16 with thiophenol 17 the key 4-thioaryl substituted intermediate 18 was obtained in 78% yield. This compound was efficiently converted to the target tricyclic products 4a and b. Compound 4a, in particular, is a potent inhibitor in vitro (IC50 = 2 nM) of wild type HIV-1 replication. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.128