9-Bromo-3,4-dihydro-2H-[1,3]thiazino[3,2-b]indazole | 1620514-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 9-Bromo-3,4-dihydro-2H-[1,3]thiazino[3,2-b]indazole
• 英文别名: 9-bromo-3,4-dihydro-2H-[1,3]thiazino[3,2-b]indazole
• CAS: 1620514-59-1
• 化学式: C₁₀H₉BrN₂S
• 分子量: 269.165
• InChiKey: YJLNDQJSEYHBAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴-2-硝基苯甲醛 在 三乙基硅烷 、 sodium cyanoborohydride 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 9-Bromo-3,4-dihydro-2H-[1,3]thiazino[3,2-b]indazole
  参考文献：
  名称：

  Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles

  摘要：

  Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1 degrees-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl) (tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.

  DOI：

  10.1021/jo501014e

文献信息

• Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2<i>H</i>-indazoles
  作者：Kelli M. Farber、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/jo501014e

  日期：2014.8.1

  Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1 degrees-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl) (tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.