(4-甲基苯基)3-氯丙酸酯 | 94102-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (4-甲基苯基)3-氯丙酸酯
• 英文名称: 4-methylphenyl-3-chloropropanoate
• 英文别名: p-tolyl 3-chloropropanoate；3-chloro-propionic acid p-tolyl ester；3-Chlor-propionsaeure-p-tolylester；4-Methylphenyl 3-Chloropropanoate；(4-methylphenyl) 3-chloropropanoate
• CAS: 94102-85-9
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: PCBWTBCGNNCPFD-UHFFFAOYSA-N

物化性质

• 沸点：
  145-150 °C(Press: 12 Torr)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-甲基苯基)3-氯丙酸酯 在 aluminum (III) chloride 作用下， 生成 7-羟基-4-甲基-1-茚酮
  参考文献：
  名称：

  Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors

  摘要：

  With the goal of improving metabolic stability and further enhancing FBPase inhibitory activity, a series of tricyclic 8H-indeno[1,2-d][1,3]thiazoles was designed and synthesized with the aid of structure-based drug design. Extensive SAR studies led to the discovery of 19a with an IC50 value of 1 nM against human FBPase. X-ray crystallographic studies revealed that high affinity of 19a was due to the hydrophobic interaction arising from better shape complementarity and to the hydrogen bonding network involving the side chain on the tricyclic scaffold. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.056
• 作为产物：
  描述：

  对甲酚 、 3-氯丙酰氯 在 柠檬酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 以12.90 g (55%)的产率得到(4-甲基苯基)3-氯丙酸酯
  参考文献：
  名称：

  Method and composition for treatment of inflammatory bowel disease

  摘要：

  一种单剂量制剂，用于抑制、预防或治疗炎症性肠病，包括一种有效量的具有以下公式的化合物和其药学可接受载体。还公开了一种用于抑制、预防或治疗炎症性肠病的方法，包括向需要的人类或非人类哺乳动物投与有效量的具有以下公式的化合物。

  公开号：

  US20030211978A1

文献信息

• Attempted novel preparation of dihydrocoumarin and coumarin; obtention of aryl acrylates and 3-chloropropionates
  作者：Jaswant R. Mahajan、Hugo C. Araújo

  DOI：10.1139/v87-035

  日期：1987.1.1

  It has been found that, contrary to the published report, there is no noticeable reaction between phenol and methyl acrylate in the presence of aluminum chloride to produce phenyl acrylate (1) and dihydrocoumarin (2). Although products having the reported spectral data can be obtained by the reaction of phenol with acrylyl chloride, these products are actually phenyl acrylate and phenyl 3-chloropropionate (4), there being detected no dihydrocoumarin. This reaction has now been extended to several substituted phenols and some naphthols. Attempts at cyclization of phenyl acrylate, phenyl 3-chloropropionate, or their mixtures have been unsuccessful.

  研究发现，与已发表的报告相反，苯酚和甲基丙烯酸酯在氯化铝存在下没有明显的反应，不能产生苯基丙烯酸酯（1）和二氢香豆素（2）。虽然通过苯酚与丙烯酰氯反应可以得到具有已报告光谱数据的产物，但事实上这些产物是苯基丙烯酸酯和苯基3-氯丙酸酯（4），没有检测到二氢香豆素。这个反应现已扩展到几种取代苯酚和一些萘酚。尝试将苯基丙烯酸酯、苯基3-氯丙酸酯或它们的混合物环化均未成功。
• Synthetische Versuche in der Reihe der Antihelmintika
  作者：K. W. Rosenmund、D. Schapiro

  DOI：10.1002/ardp.19342721017

  日期：——
• Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators
  作者：Raymond J. Bergeron、Jan Wiegand、William R. Weimar、J. R. Timothy Vinson、Jörg Bussenius、Guo Wei Yao、James S. McManis

  DOI：10.1021/jm980340j

  日期：1999.1.1

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
• Dann et al., Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 16,36
  作者：Dann et al.

  DOI：——

  日期：——
• Magagnini,P.L.; Pizzirani,G., Gazzetta Chimica Italiana, 1966, vol. 96, p. 1035 - 1045
  作者：Magagnini,P.L.、Pizzirani,G.

  DOI：——

  日期：——