N-(1-tosylethyl)urea | 851228-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-tosylethyl)urea
• 英文别名: N-[1-(4-Methylbenzene-1-sulfonyl)ethyl]urea；1-(4-methylphenyl)sulfonylethylurea
• CAS: 851228-15-4
• 化学式: C₁₀H₁₄N₂O₃S
• 分子量: 242.299
• InChiKey: CJMHRZBYASGKAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.4±45.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-tosylethyl)urea 、 三氟乙酰乙酸乙酯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 6.17h， 以1.212 g的产率得到ethyl 4-hydroxy-4-(trifluoromethyl)-6-methyl-2-oxohexahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A new synthesis of 4- or/and 6-CF3-containing hexahydro- and 1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A novel simple approach to 4- or/and 6-trifluoromethyl-substituted 5-acylhexahydro- and 5-acyl-,2,3,4-tetrahydropyrimidin-2-ones has been developed. The method is based on an amidoallcylation reaction using CF3-containing building blocks, namely, Na-enolates of 1,3-dicarbonyl compounds and N(1-tosylalkyl)- or N-(1-acetoxyallcyl)ureas. The obtained products, 4-hydroxyhexahydropyrimidin-2-ones or their acyclic isomers were dehydrated under the action of TsOH to give corresponding tetrahydropyrimidin-2-ones. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.11.008
• 作为产物：
  描述：

  对甲苯亚磺酸 、 乙醛 、 尿素 以 水 为溶剂， 反应 2.25h， 生成 N-(1-tosylethyl)urea
  参考文献：
  名称：

  A new synthesis of 4- or/and 6-CF3-containing hexahydro- and 1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A novel simple approach to 4- or/and 6-trifluoromethyl-substituted 5-acylhexahydro- and 5-acyl-,2,3,4-tetrahydropyrimidin-2-ones has been developed. The method is based on an amidoallcylation reaction using CF3-containing building blocks, namely, Na-enolates of 1,3-dicarbonyl compounds and N(1-tosylalkyl)- or N-(1-acetoxyallcyl)ureas. The obtained products, 4-hydroxyhexahydropyrimidin-2-ones or their acyclic isomers were dehydrated under the action of TsOH to give corresponding tetrahydropyrimidin-2-ones. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.11.008

文献信息

• A General Approach to 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) via α-(thio)ureidoalkylation of 1,3-diketones or β-oxoesters
  作者：Anatoly D. Shutalev、Anastasia A. Fesenko、Elena D. Strel’tsova

  DOI：10.1007/s10593-023-03146-6

  日期：2022.12

  A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N-[alkyl(tosyl)methyl]thioureas, N-(azidomethyl)thiourea, and N-[alkyl(tosyl)methyl]ureas followed by TsOH-catalyzed dehydration of the intermediate 4-hydroxyhexahydropyrimidine-2-thiones(ones) without or with isolation of the latter.

  我们开发出了一种新的通用方法，可用于制备迄今为止难以获得的大量 4-未取代和 4-烷基取代的 5-酰基-1,2,3,4-四氢嘧啶-2-亚硫酰（一）。该方法基于各种 1,3-二酮或β-氧代酯的烯醇化物与容易获得的 N-[烷基（甲苯基）甲基]硫脲、N-（叠氮甲基）硫脲和 N-[烷基（甲苯基）甲基]脲反应，然后在 TsOH 催化下对中间体 4-羟基六氢嘧啶-2-硫酮（一）进行脱水，而不分离或分离后者。
• A new synthesis of 4- or/and 6-CF3-containing hexahydro- and 1,2,3,4-tetrahydropyrimidin-2-ones
  作者：Pavel A. Solovyev、Anastasia A. Fesenko、Anatoly D. Shutalev

  DOI：10.1016/j.jfluchem.2015.11.008

  日期：2016.2

  A novel simple approach to 4- or/and 6-trifluoromethyl-substituted 5-acylhexahydro- and 5-acyl-,2,3,4-tetrahydropyrimidin-2-ones has been developed. The method is based on an amidoallcylation reaction using CF3-containing building blocks, namely, Na-enolates of 1,3-dicarbonyl compounds and N(1-tosylalkyl)- or N-(1-acetoxyallcyl)ureas. The obtained products, 4-hydroxyhexahydropyrimidin-2-ones or their acyclic isomers were dehydrated under the action of TsOH to give corresponding tetrahydropyrimidin-2-ones. (C) 2015 Elsevier B.V. All rights reserved.