(4-hydroxy-phenyl)-carbamic acid butyl ester | 83264-09-9

• 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: (4-hydroxy-phenyl)-carbamic acid butyl ester
• 英文别名: (4-Hydroxy-phenyl)-carbamidsaeure-butylester；butyl N-(4-hydroxyphenyl)carbamate
• CAS: 83264-09-9
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: YQNYEBWANVIHJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-phenyl)-carbamic acid butyl ester 在 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 48.0h， 生成 4-{[(2-hydroxy-3-{4-[(butoxycarbonyl)amino]phenoxy}propyl)azaniumyl]methyl}-1-butylpiperidin-1-ium dimethanesulfonate
  参考文献：
  名称：

  An integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors

  摘要：

  Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new molecular target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. Our theoretical and experimental study has allowed us to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. Our study was carried out in different steps: virtual screening, synthesis, bioassays and molecular modelling. From our results, we propose a new dihydrobenzo[b] pyrimido[5,4-f]azepine and two alkyl{3-/4-[-1-hydroxy-2-(4-arylpiperazin-1-yl)ethyliphenyl}carbamates as initial structures for the development of new inhibitors. In addition, our molecular modelling study using QTAIM calculations, allowed us to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined in order to obtain an increase in the binding affinity of these ligands. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.08.017
• 作为产物：
  描述：

  对氨基苯酚 、 氯甲酸丁酯 以 乙醚 为溶剂， 反应 1.0h， 生成 (4-hydroxy-phenyl)-carbamic acid butyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of new β-adrenoreceptor antagonists. Evidence for the electrostatic requirements for β-adrenoreceptor antagonists

  摘要：

  A series of mono- and disubstituted phenoxypropanolamines, structurally related to practolol and acebutolol, has been synthesized and tested for beta-adrenoreceptor blocking activity. Structure-activity relationships are discussed. The reasons for the lack of activity of compounds 3n and 4n have also been examined. The results suggest that the negative electrostatic potential above the phenyl ring of phenoxypropanolamines is essential for binding activity and point to the presence of an electropositive residue in the beta-adrenoreceptor binding site.

  DOI：

  10.1016/0223-5234(91)90127-9

文献信息

• Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates
  作者：Shahnaz Perveen、Arfa Yasmin、Khalid Mohammed Khan

  DOI：10.1080/14786410802270738

  日期：2010.1.10

  The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.

  异氰酸酯和异硫氰酸酯与长链醇，例如将反应Ñ己醇，Ñ庚醇和Ñ辛醇，只给Ñ -芳基- ø -烷基氨基甲酸盐，而Ñ -芳基- ö烷基用对称沿形成氨基甲酸酯当在不使用任何溶剂的情况下与小链醇在室温下进行相同的反应时，1,3-二取代的脲和硫脲。
• Chabrier et al., Bulletin de la Societe Chimique de France, 1955, p. 1353,1358
  作者：Chabrier et al.

  DOI：——

  日期：——
• CSOLLEI, JOZEF;BOROVANSKY, ALOIS;BENES, LUDEK
  作者：CSOLLEI, JOZEF、BOROVANSKY, ALOIS、BENES, LUDEK

  DOI：——

  日期：——
• CSOLLEI, J.;BOROVANSKY, A.;BENES, L.;BEDEROVA, E.;SVEC, P., CS. FARM., 1982, 31, N 6, 229-235
  作者：CSOLLEI, J.、BOROVANSKY, A.、BENES, L.、BEDEROVA, E.、SVEC, P.

  DOI：——

  日期：——
• AMINOHETEROCYCLIC DERIVATIVES AS ANTITHROMBOTIC OR ANTICOAGULANT AGENTS
  申请人：ZENECA LIMITED

  公开号：EP0880502A1

  公开（公告）日：1998-12-02