1-[(dimethylcarbamoyl)methyl]thiourea | 154140-01-9

• 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: 1-[(dimethylcarbamoyl)methyl]thiourea
• 英文别名: 2-(carbamothioylamino)-N,N-dimethylacetamide
• CAS: 154140-01-9
• 化学式: C₅H₁₁N₃OS
• 分子量: 161.228
• InChiKey: UZDXTTSUUABKKO-UHFFFAOYSA-N

物化性质

• 沸点：
  294.9±42.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-二甲氧基苯酚酯 、 1-[(dimethylcarbamoyl)methyl]thiourea 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 以45%的产率得到2-(5,5-di(4-methoxyphenyl)-thiohydantoin-3-yl)-N,N-dimethylacetamide
  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 、 二甲胺 反应 12.0h， 生成 1-[(dimethylcarbamoyl)methyl]thiourea
  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

• Utilization of α-halocarbonyl compounds in the synthesis of thiazole, thiadiazole, and thiophene derivatives
  作者：Ehab Abdel-latif、Samir Bondock

  DOI：10.1002/hc.20206

  日期：2006.4

  toward a variety of several α-halo- carbonyl compounds was investigated. Thus, reaction of 1 with α-bromoketones, hydrazonoyl bromides, and 2-chloro-N-arylacetamides afforded the corresponding dihydrothiazole, 1,3,4-thiadiazole, and thiophene derivatives, respectively. The synthesis of thiazolidin-4-one 11, thiazolidin-5-one 12, and some azo derivatives of thiazolidin-5-one were described. 5-Arylazothiazoles

  研究了 2-苯基硫代氨基甲酰乙酸乙酯 1 对多种 α-卤代羰基化合物的行为。因此，1 与 α-溴酮、腙酰溴和 2-氯-N-芳基乙酰胺反应分别得到相应的二氢噻唑、1,3,4-噻二唑和噻吩衍生物。描述了 thiazolidin-4-one 11、thiazolidin-5-one 12 和 thiazolidin-5-one 的一些偶氮衍生物的合成。5-芳基偶氮噻唑 17 和 19 是通过腙酰溴 3 与不同硫脲衍生物的缩合反应合成的。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:299–305, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20206
• Versatile Synthesis of N,S-Heterocycles Containing the Antipyrine Moiety
  作者：E. Abdel-Latif

  DOI：10.1080/104265090969054

  日期：2006.1.1

  A series of novel sulfide derivatives of expected biological activity were synthesized via the reaction of 4-(chloroacetyl)antipyrine (1) with several sulfur nucleophiles. The quantitatively available 2-aminothiazole derivatives 10 and 11 were coupled with pyrazolopyridinyl and aromatic diazonium salts to furnish a new series of the corresponding pyrazolopyridinylazo and arylazo-thiazole dyes 12 and

  通过 4-（氯乙酰基）安替比林 (1) 与几种硫亲核试剂的反应，合成了一系列具有预期生物活性的新型硫化物衍生物。定量可用的 2-氨基噻唑衍生物 10 和 11 与吡唑并吡啶基和芳族重氮盐偶联，以提供一系列新的相应吡唑并吡啶基和芳基-噻唑染料 12 和 13。 4-（氰基乙酰基）安替比林 (14) 与苯基的反应异硫氰酸酯提供了不可分离的加合物 15，它被用作合成多官能取代的烯酮 N,S-缩醛、二氢噻唑和噻唑烷酮环系统的前体。
• 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.