N-Cinnamoyl-N'-(1-dimethylamino-2-phenylbut-2-eneylidene)sulfamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-Cinnamoyl-N'-(1-dimethylamino-2-phenylbut-2-eneylidene)sulfamide
• 英文别名: (E)-N-[(Z)-[(E)-1-(dimethylamino)-2-phenylbut-2-enylidene]amino]sulfonyl-3-phenylprop-2-enamide
• 化学式: C₂₁H₂₃N₃O₃S
• 分子量: 397.498
• InChiKey: BDAIHUXXMWHTJD-YXGMJKJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  trans-cinnamoylsulfamoyl chloride 在 silica gel 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 N-Cinnamoyl-N'-(1-dimethylamino-2-phenylbut-2-eneylidene)sulfamide
  参考文献：
  名称：

  Novel reactions of N-sulfonylamines with 3-dimethylamino-2H-azirines. Competitive formation of 1,2,5-thiadiazoles, 1,2,3-oxathiazoles and acrylamidines. X-Ray molecular structure of N-(4-dimethylamino-5-methyl-2-oxo-5-phenyl-5H-1,2λ⁶,3-oxathiazol-2-ylidene)benzamide

  摘要：

  Reaction of 3-dimethylamino-2,2-diphenyl-2H-azirine 3a with N-sulfonylalkylamines 2a,b provides 1,2,5-thiadiazoles 5a,b, whereas use of N-carbonylsulfonylamines 2c,e as reaction partners primarily results in 1,2,3-oxathiazoles 6a,b which isomerise to the corresponding thiadiazoles 5c,d on treatment with silica gel at room temperature. In contrast, use of 2-alkyl-3-dimethylamino-2-phenyl-2H-azir 3b,c in the reaction with the N-sulfonylamide 2c and the N-sulfonylcarbamates 2e,f leads to mixtures of thiadiazoles 5 and oxathiazoles 6 along with isomeric acrylamidines 7.

  DOI：

  10.1039/p19960001629

文献信息

• Novel reactions of N-sulfonylamines with 3-dimethylamino-2H-azirines. Competitive formation of 1,2,5-thiadiazoles, 1,2,3-oxathiazoles and acrylamidines. X-Ray molecular structure of N-(4-dimethylamino-5-methyl-2-oxo-5-phenyl-5H-1,2λ⁶,3-oxathiazol-2-ylidene)benzamide
  作者：Ingo Tornus、Ernst Schaumann、Gunadi Adiwidjaja

  DOI：10.1039/p19960001629

  日期：——

  Reaction of 3-dimethylamino-2,2-diphenyl-2H-azirine 3a with N-sulfonylalkylamines 2a,b provides 1,2,5-thiadiazoles 5a,b, whereas use of N-carbonylsulfonylamines 2c,e as reaction partners primarily results in 1,2,3-oxathiazoles 6a,b which isomerise to the corresponding thiadiazoles 5c,d on treatment with silica gel at room temperature. In contrast, use of 2-alkyl-3-dimethylamino-2-phenyl-2H-azir 3b,c in the reaction with the N-sulfonylamide 2c and the N-sulfonylcarbamates 2e,f leads to mixtures of thiadiazoles 5 and oxathiazoles 6 along with isomeric acrylamidines 7.