1-(3-Chloro-4-fluorophenyl)-3-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]thiourea | 380304-57-4

• 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: 1-(3-Chloro-4-fluorophenyl)-3-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]thiourea
• CAS: 380304-57-4
• 化学式: C₁₁H₁₄ClFN₂O₃S
• 分子量: 308.761
• InChiKey: UJTYMIZRIRVIAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  516.0±60.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  117
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-Chloro-4-fluorophenyl)-3-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]thiourea 在 mercury(II) oxide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 24.0h， 以39%的产率得到[2-(3-chloro-4-fluoroanilino)-4-(hydroxymethyl)-5H-1,3-oxazol-4-yl]methanol
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of Fluorine-Containing 4,4-Dihydroxylmethyl-2-aryliminooxazo(thiazo)lidines as Trehalase Inhibitors

  摘要：

  Five fluorine-containing 4,4-dihydroxylmethyl-2-aryliminooxazolidines and five 4,4-dihydroxylmethyl-2-aryliminothiazolidines were synthesized and evaluated for their inhibitory activity against trehalase in vitro. All these compounds were very readily synthesized compared with the natural trehalase inhibitors. They had moderate inhibitory activity toward trehalase, and showed larvicidal activity and inhibition action to insect flight. The steric parameters and semiempirical quantum parameters of these compounds were acquired by using the molecular modeling method and the PM3-SCF-MO method, respectively. A quantitative structure-activity relationship between half-inhibitory concentrations toward trehalase and the above parameters was established.

  DOI：

  10.1021/jf010632k
• 作为产物：
  描述：

  在 氯甲酸乙酯 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 12.67h， 生成 1-(3-Chloro-4-fluorophenyl)-3-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]thiourea
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of Fluorine-Containing 4,4-Dihydroxylmethyl-2-aryliminooxazo(thiazo)lidines as Trehalase Inhibitors

  摘要：

  Five fluorine-containing 4,4-dihydroxylmethyl-2-aryliminooxazolidines and five 4,4-dihydroxylmethyl-2-aryliminothiazolidines were synthesized and evaluated for their inhibitory activity against trehalase in vitro. All these compounds were very readily synthesized compared with the natural trehalase inhibitors. They had moderate inhibitory activity toward trehalase, and showed larvicidal activity and inhibition action to insect flight. The steric parameters and semiempirical quantum parameters of these compounds were acquired by using the molecular modeling method and the PM3-SCF-MO method, respectively. A quantitative structure-activity relationship between half-inhibitory concentrations toward trehalase and the above parameters was established.

  DOI：

  10.1021/jf010632k

文献信息

• Syntheses, structures and bioactivities of fluorine-containing phenylimino-thia(oxa)zolidine derivatives as agricultural bioregulators
  作者：Xuhong Qian、Xiaoyong Xu、Zhibin Li、Zhong Li、Gonghua Song

  DOI：10.1016/j.jfluchem.2004.09.002

  日期：2004.11

  From insight into the structure of trehazolin as trehalase inhibitor, six series of fluorine-containing phenylimino-thiazolidines (oxazolidines) derivatives were designed and prepared through a convenient synthesis of fluoroaryl isothiocyanate and a one-pot facile synthesis in high yield of fluorophenyl aminobenzoxazoles by cyclodesulfurization. The structures of the target compounds were confirmed with using IR, NMR, MS and elemental analysis. Their X-ray crystal analysis suggested that there were novel intermolecular (sp(2)CF(...)H(3)C-) and intramolecular (sp(2)CF(...)HN) hydrogen bonds between the fluorine atom on benzene ring and hydrogen atom of methyl group or amino group on five-membered heterocycle. Their fungicidal activities against Rhizoctonia solani and Pyricuraria oryzae at 100 ppm were determined. (C) 2004 Elsevier B.V. All rights reserved.
• Synthesis and Quantitative Structure−Activity Relationships of Fluorine-Containing 4,4-Dihydroxylmethyl-2-aryliminooxazo(thiazo)lidines as Trehalase Inhibitors
  作者：Xuhong Qian、Zhi Liu、Zhibin Li、Zhong Li、Gonghua Song

  DOI：10.1021/jf010632k

  日期：2001.11.1

  Five fluorine-containing 4,4-dihydroxylmethyl-2-aryliminooxazolidines and five 4,4-dihydroxylmethyl-2-aryliminothiazolidines were synthesized and evaluated for their inhibitory activity against trehalase in vitro. All these compounds were very readily synthesized compared with the natural trehalase inhibitors. They had moderate inhibitory activity toward trehalase, and showed larvicidal activity and inhibition action to insect flight. The steric parameters and semiempirical quantum parameters of these compounds were acquired by using the molecular modeling method and the PM3-SCF-MO method, respectively. A quantitative structure-activity relationship between half-inhibitory concentrations toward trehalase and the above parameters was established.