2-(carbamothioylamino)-N-methylacetamide | 93234-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(carbamothioylamino)-N-methylacetamide
• CAS: 93234-53-8
• 化学式: C₄H₉N₃OS
• 分子量: 147.201
• InChiKey: XGLOTPVXAOGUNO-UHFFFAOYSA-N

物化性质

• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 2-(carbamothioylamino)-N-methylacetamide 以 乙醇 为溶剂， 反应 2.0h， 以59%的产率得到2-imino-5-[(Z)-methoxycarbonylmethylene]-3-(N-methyl-2-acetamidyl)-thiazolidin-4-one
  参考文献：
  名称：

  Heterocycles by cascade reactions of versatile thioureido-acetamides

  摘要：

  Thioureido-acetamides (1) are quantitatively accessible by gas-solid reaction of amines with thiohydantoins. They are useful starting materials for various heterocyclic syntheses in one-pot cascade reactions with excellent atom economy: 2-iminothiazoles (5) are quantitatively formed from 1 and phenacyl bromide in the solid state. Thioparabanic acids (9) are easily accessible from oxalyl dichloride and 1. Benzils react with 1 to afford functionalized 5,5-diaryl-thiohydantoins (14) and dimethylacetylene dicarboxylate gives 2-imino-5-methylene-thiazolidine-4-ones (17) and (18) upon reaction with 1. The one-pot syntheses of imidazo[1,2-c]pyrimidines (25) and (28) from 1 with benzaldehydes and ethyl cyanoacetate or malodinitrile are benign new accesses to these important heterocycles. All product structures are determined from spectroscopic and chemical data and preferred tautomers are judged by DFT calculations at the B3LYP/6-31G* level. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00794-9
• 作为产物：
  描述：

  2-硫代乙内酰脲 、 甲胺 反应 12.0h， 生成 2-(carbamothioylamino)-N-methylacetamide
  参考文献：
  名称：

  Kaupp, Gerd; Schmeyers, Jens, Angewandte Chemie, 1993, vol. 105, # 11, p. 1656 - 1658

  摘要：

  DOI：

文献信息

• Kaupp, Gerd; Schmeyers, Jens, Angewandte Chemie, 1993, vol. 105, # 11, p. 1656 - 1658
  作者：Kaupp, Gerd、Schmeyers, Jens

  DOI：——

  日期：——
• Heterocycles by cascade reactions of versatile thioureido-acetamides
  作者：Jens Schmeyers、Gerd Kaupp

  DOI：10.1016/s0040-4020(02)00794-9

  日期：2002.9

  Thioureido-acetamides (1) are quantitatively accessible by gas-solid reaction of amines with thiohydantoins. They are useful starting materials for various heterocyclic syntheses in one-pot cascade reactions with excellent atom economy: 2-iminothiazoles (5) are quantitatively formed from 1 and phenacyl bromide in the solid state. Thioparabanic acids (9) are easily accessible from oxalyl dichloride and 1. Benzils react with 1 to afford functionalized 5,5-diaryl-thiohydantoins (14) and dimethylacetylene dicarboxylate gives 2-imino-5-methylene-thiazolidine-4-ones (17) and (18) upon reaction with 1. The one-pot syntheses of imidazo[1,2-c]pyrimidines (25) and (28) from 1 with benzaldehydes and ethyl cyanoacetate or malodinitrile are benign new accesses to these important heterocycles. All product structures are determined from spectroscopic and chemical data and preferred tautomers are judged by DFT calculations at the B3LYP/6-31G* level. (C) 2002 Elsevier Science Ltd. All rights reserved.