3-(3-benzyl-thioureido)-propanoic acid | 139059-59-9

• 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: 3-(3-benzyl-thioureido)-propanoic acid
• 英文别名: 1-(2-carboxyethyl) 3-benzylthiouree；3-(Benzylcarbamothioylamino)propanoic acid
• CAS: 139059-59-9
• 化学式: C₁₁H₁₄N₂O₂S
• 分子量: 238.31
• InChiKey: BJIVPNOSNOFGOD-UHFFFAOYSA-N

物化性质

• 沸点：
  422.4±55.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异丁酸酐 、 3-(3-benzyl-thioureido)-propanoic acid 反应 6.0h， 以48%的产率得到
  参考文献：
  名称：

  Formation of dihydrouracils via cyclization of N-substituted 3-thioureidopropanoic acids and facile desulfurization

  摘要：

  Cyclization of N-3 substituted 3-thioureidopropanoic acids in isobutyric anhydride at high temperature resulted in the unexpected formation of N-3, N-1-substituted dihydrouracils, as confirmed by thorough spectroscopic characterization. A mechanism based on the identification of intermediates observed at lower reaction temperatures is proposed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.042
• 作为产物：
  描述：

  异硫氰酸苯甲酯 、 β-丙氨酸 生成 3-(3-benzyl-thioureido)-propanoic acid
  参考文献：
  名称：

  Formation of dihydrouracils via cyclization of N-substituted 3-thioureidopropanoic acids and facile desulfurization

  摘要：

  Cyclization of N-3 substituted 3-thioureidopropanoic acids in isobutyric anhydride at high temperature resulted in the unexpected formation of N-3, N-1-substituted dihydrouracils, as confirmed by thorough spectroscopic characterization. A mechanism based on the identification of intermediates observed at lower reaction temperatures is proposed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.042

文献信息

• Synthèse, activité antiparasitaire et antifongique de thiouréines à motif aminoacide
  作者：R Caujolle、M Payard、PR Loiseau、H Amarouch、MD Linas、JP Séguéla、C Bories、PM Loiseau、P Gayral

  DOI：10.1016/0223-5234(91)90122-4

  日期：1991.10

  Sixteen compounds, close to aryl or aralkylthioureines, with a beta-alanine or gamma-aminobutyric acid chain, were synthesized for in vitro screening towards 3 types of nematodes, 8 classes of opportunist germs and 34 classes of yeasts. Their anthelminthic activity was very weak, but on the other hand, 7 compounds were effective against yeasts and/or opportunist germs, with an MIC < 50-mu-g/ml.
• Formation of dihydrouracils via cyclization of N-substituted 3-thioureidopropanoic acids and facile desulfurization
  作者：Carina M.L. Delpiccolo、Fernando Albericio、Robert A. Schiksnis、Enrique L. Michelotti

  DOI：10.1016/j.tet.2007.06.042

  日期：2007.9

  Cyclization of N-3 substituted 3-thioureidopropanoic acids in isobutyric anhydride at high temperature resulted in the unexpected formation of N-3, N-1-substituted dihydrouracils, as confirmed by thorough spectroscopic characterization. A mechanism based on the identification of intermediates observed at lower reaction temperatures is proposed. (C) 2007 Elsevier Ltd. All rights reserved.