6-bromo-3-(2-thioxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-chromen-2-one | 1373166-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-bromo-3-(2-thioxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-chromen-2-one
• 英文别名: 6-Bromo-3-(2-sulfanylidene-3,6-dihydro-1,3,4-thiadiazin-5-yl)chromen-2-one；6-bromo-3-(2-sulfanylidene-3,6-dihydro-1,3,4-thiadiazin-5-yl)chromen-2-one
• CAS: 1373166-07-4
• 化学式: C₁₂H₇BrN₂O₂S₂
• 分子量: 355.236
• InChiKey: WBGAGZDLZYYMTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-bromo-3-(2-bromoacetyl)-2H-chromen-2-one 在 盐酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 6-bromo-3-(2-thioxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-chromen-2-one
  参考文献：
  名称：

  Synthesis of Coumarin-Substituted 1,3,4-Thiadizine-2-thiones and 1,3-Thiazoline-2-thiones

  摘要：

  Interaction of phenyl hydrazine / hydrazine with carbon disulfide in the presence of KOH affords the corresponding potassium salts of dithioformates. These in situ generated salts were reacted with different 3-(2-bromoacetyl)coumarins to yield N-1-phenyl-hydrazinecarbodithioic acid 2-oxo-2-(2-oxo-2H-chromen-3-yl)-ethyl ester (4a-c) and hydrazinecarbodithioic acid 2-oxo-2-(2-oxo-2H-chromen-3-yl)-ethyl ester (7a-c) respectively. Cyclocondensation of these compounds in the presence of an acid gave 3-(3-phenylamino-2-thioxo-2,3-dihydro-thiazol-4-yl)-chromen-2-ones (5a-c) and 3-(2-thioxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-chromen-2-ones (8a-c) respectively.

  DOI：

  10.1080/00397911.2010.551698

文献信息

• Synthesis of Coumarin-Substituted 1,3,4-Thiadizine-2-thiones and 1,3-Thiazoline-2-thiones
  作者：Venkata Sreenivasa Rao Chunduru、Rajeswar Rao Vedula

  DOI：10.1080/00397911.2010.551698

  日期：2012.7.1

  Interaction of phenyl hydrazine / hydrazine with carbon disulfide in the presence of KOH affords the corresponding potassium salts of dithioformates. These in situ generated salts were reacted with different 3-(2-bromoacetyl)coumarins to yield N-1-phenyl-hydrazinecarbodithioic acid 2-oxo-2-(2-oxo-2H-chromen-3-yl)-ethyl ester (4a-c) and hydrazinecarbodithioic acid 2-oxo-2-(2-oxo-2H-chromen-3-yl)-ethyl ester (7a-c) respectively. Cyclocondensation of these compounds in the presence of an acid gave 3-(3-phenylamino-2-thioxo-2,3-dihydro-thiazol-4-yl)-chromen-2-ones (5a-c) and 3-(2-thioxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-chromen-2-ones (8a-c) respectively.