N1-phenyl-hydrazinecarbodithioic acid 2-(6,8-dibromo-2-oxo-2Hchromen-3-yl)-2-oxo-ethyl ester | 1373166-02-9

• 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: N1-phenyl-hydrazinecarbodithioic acid 2-(6,8-dibromo-2-oxo-2Hchromen-3-yl)-2-oxo-ethyl ester
• 英文别名: [2-(6,8-dibromo-2-oxochromen-3-yl)-2-oxoethyl] N-anilinocarbamodithioate
• CAS: 1373166-02-9
• 化学式: C₁₈H₁₂Br₂N₂O₃S₂
• 分子量: 528.245
• InChiKey: WYBDJSLXBGSECT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N1-phenyl-hydrazinecarbodithioic acid 2-(6,8-dibromo-2-oxo-2Hchromen-3-yl)-2-oxo-ethyl ester 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以76%的产率得到6,8-dibromo-3-(3-phenylamino-2-thioxo-2,3-dihydro-thiazol-4-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
• 作为产物：
  描述：

  二硫化碳 、 6,8-二溴-3-(2-溴乙酰基)香豆素 、 苯肼 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到N1-phenyl-hydrazinecarbodithioic acid 2-(6,8-dibromo-2-oxo-2Hchromen-3-yl)-2-oxo-ethyl ester
  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.