ethyl [2-(4-methylbenzoyl)-4-methylphenoxy]acetate | 807643-19-2

• 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: ethyl [2-(4-methylbenzoyl)-4-methylphenoxy]acetate
• 英文别名: Ethyl 2-[4-methyl-2-(4-methylbenzoyl)phenoxy]acetate
• CAS: 807643-19-2
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: GUGHRJLGLJFTQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59 °C(Solv: ethanol (64-17-5))
• 沸点：
  471.4±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl [2-(4-methylbenzoyl)-4-methylphenoxy]acetate 在 氢氧化钾 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 [5-methyl-2-[(2-thioxo-3H-1,3,4-oxadiazol-5-yl)methoxy]phenyl]-(p-tolyl)methanone
  参考文献：
  名称：

  Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones

  摘要：

  The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones la-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylarytoxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.005
• 作为产物：
  描述：

  (2-hydroxy-5-methylphenyl)(p-tolyl)methanone 、 氯乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以79%的产率得到ethyl [2-(4-methylbenzoyl)-4-methylphenoxy]acetate
  参考文献：
  名称：

  靶向血管生成和凋亡的新型香豆素类似物的合成及其抑癌活性

  摘要：

  通过多步合成从羟基二苯甲酮（1a – j）获得了香豆素类似物5a – j的序列。在体外的标题化合物的抗增殖作用是对艾氏腹水癌（EAC）和道尔顿淋巴瘤腹水（DLA）细胞系进行测试。在该系列中，在二苯甲酮部分中具有溴基的化合物5c具有出色的抗增殖潜能，IC 50值很高。此外，化合物5c对鼠EAC和实体DL肿瘤模型系统的体内抗肿瘤作用通过延长的存活期得到证实。复方的抑瘤机制5c是由于抗血管生成和促进细胞凋亡。这些结果表明化合物5c的可能应用，其可以在不久的将来被开发为有效的抗癌药。

  DOI：

  10.1016/j.ejmech.2014.01.050

文献信息

• A facile synthesis of dihydrobenzofuranols by photocyclization of (2-alkoxy-5-methyl-phenyl)(aryl) methanone and ethyl 2-aroyl-4-methylphenyloxyacetates
  作者：S. Shashikanth、B. S. Sudha、S. A. Khanum

  DOI：10.1002/hc.20111

  日期：——

  acetonitrile underwent photocyclization to substituted dihydrobenzofuranols 3a–i with 3a–c in very less yield being racemate and 3d–i in good yield being mixture of cis-trans isomers showing high stereoselectivity in benzene and decreased stereoselectivity in acetonitrile. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:212–217, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI

  2-烷氧基取代的二苯甲酮 2a-f 和 2-芳酰基-4-甲基苯氧基乙酸乙酯 2g-i 在苯和乙腈中的辐照经过光环化反应生成取代的二氢苯并呋喃醇 3a-i，其中 3a-c 的产率非常低，外消旋物和 3d-i 在顺反异构体混合物的产率良好，在苯中显示出高立体选择性，在乙腈中显示出立体选择性降低。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:212–217, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20111
• Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles
  作者：V. Girish、Noor Fatima Khanum、H. D. Gurupadaswamy、Shaukath Ara Khanum

  DOI：10.1134/s1068162014030066

  日期：2014.5

  Synthetic pathway of the ten novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles as new potential antimicrobial agents is illustrated. Intramolecular cyclization of 2-(2-aroylaryloxy) aceto hydrazides to 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles was achieved with triethyl orthoformate in good yields. The compounds were characterized by IR, H-1 NMR, mass spectra and by means of CHN analysis. The target compounds were tested for their in vitro antimicrobial activity against representative strains by disc diffusion method and micro dilution methods. Several compounds showed antimicrobial activity comparable with or higher than the standard drugs.