ethyl (m-acetylphenyl)acetate | 14194-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (m-acetylphenyl)acetate
• 英文别名: (3-acetylphenyl)acetate；ethyl 2-(3-acetylphenyl)acetate；m-Acetyl-phenylessigsaeure-ethylester；(3-acetyl-phenyl)-acetic acid ethyl ester；(3-Acetyl-phenyl)-essigsaeure-aethylester
• CAS: 14194-05-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: OIBZTNBTHXRNCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  118 °C(Press: 0.5 Torr)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (m-acetylphenyl)acetate 在 sodium hydroxide 、 硫酸 、 碘 作用下， 生成 3-(羧基甲基)苯甲酸
  参考文献：
  名称：

  Friedel-Crafts酮合成中的反常取向。

  摘要：

  DOI：

  10.1021/ja01215a002
• 作为产物：
  描述：

  3'-溴苯乙酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 苄基三乙基氯化铵 、 potassium acetate 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 ethyl (m-acetylphenyl)acetate
  参考文献：
  名称：

  [EN] OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY
  [FR] OXINDOLES SUBSTITUÉS PAR OLÉFINE AYANT UNE ACTIVITÉ SUR AMPK

  摘要：

  本发明涉及具有有价值的药理特性的式(I)化合物，特别是AMPK激活剂，因此在治疗某些可以通过激活该受体预防或治疗的疾病方面具有用处。这些化合物适用于治疗和预防可以受该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。

  公开号：

  WO2014202528A1

文献信息

• Enolate Anions. II. Substituent Effects of Sodium Ethyl Phenylacetates in DMSO
  作者：Syun-ichi Kiyooka、Yoshinobu Ueda、Kojiro Suzuki

  DOI：10.1246/bcsj.53.1656

  日期：1980.6

  The UV-visible, IR, and 1H-NMR spectra of the sodium enolates of ethyl phenylacetates (substituents; p-CH3O, p-CH3, m-CH3, H, p-Cl, p-CH3CO, m-CH3CO, p-COOC2H5, p-CN, and p-NO2) in DMSO were measured at room temperature. The derivatives with electron-attracting groups at the para position exhibit their absorption maxima with e>104 in visible regions above 400 nm. The visible spectra suggest the presence

  苯乙酸乙酯（取代基；p-CH3O、p-CH3、m-CH3、H、p-Cl、p-CH3CO、m-CH3CO、p-在室温下测量 DMSO 中的 COOC2H5、p-CN 和 p-NO2)。在对位具有吸电子基团的衍生物在 400 nm 以上的可见光区域显示出其吸收最大值，e>104。可见光谱表明它们在对位的吸电子基团和通过苯环的烯醇阴离子部分之间存在共振。红外光谱中烯醇化物的羰基伸缩振动和 1H-NMR 光谱中烯醇化物的残留次甲基质子的化学位移可以通过使用取代基常数 σ 和 σ- 很好地解释。meta 线和 para 线的 ρ 值差别很大。
• Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids
  作者：Guojiao Wu、Yifan Deng、Chaoqiang Wu、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201406765

  日期：2014.9.22

  Transition‐metal‐free synthesis of α‐aryl esters and nitriles using arylboronic acids with α‐aminoesters and α‐aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)N bonds into C(sp3)C(sp2) bonds. The reaction conditions are mild, demonstrate good functional‐group tolerance, and can be scaled up.

  已开发出分别使用芳基硼酸与α-氨基酯和α-氨基乙腈作为原料的无过渡金属合成α-芳基酯和腈的方法。该反应代表了将C（sp 3）N键转换为C（sp 3）C（sp 2）键的罕见情况。反应条件温和，表现出良好的官能团耐受性，并且可以扩大规模。
• Regioselective Acylation of (5-Alkylidene-1,3-cyclohexadiene)tricarbonyliron Complexes by the Reaction with Organometallic Reagents
  作者：Mitsuhiko Iwakoshi、Soo Ho Ban、Yujiro Hayashi、Koichi Narasaka

  DOI：10.1246/cl.1998.395

  日期：1998.5

  Reaction of [(1,2,3,4-η)-5-alkylidene-1,3-cyclohexadiene]tricarbonylirons and organometallic reagents generates acyl[(1,2,3,4,5-η)-1-alkylcyclohexadienyl]dicarbonylirons. The acyl group in these complexes migrates to the cyclohexadienyl moiety under carbon monoxide atmosphere, providing [(1,2,3,4-η)-6-acyl-2-alkyl-1,3-cyclohexadiene]tricarbonylirons, which are further transformed to m-alkylphenyl ketones

  [(1,2,3,4-η)-5-亚烷基-1,3-环己二烯]三羰基铁与有机金属试剂反应生成酰基[(1,2,3,4,5-η)-1-烷基环己二烯基]二羰基铁。这些配合物中的酰基在一氧化碳气氛下迁移到环己二烯基部分，提供[(1,2,3,4-η)-6-acyl-2-烷基-1,3-环己二烯]三羰基铁，进一步转化用三甲胺 N-氧化物氧化成间烷基苯基酮。
• Borsche; Sinn, Justus Liebigs Annalen der Chemie, 1942, vol. 553, p. 260,267
  作者：Borsche、Sinn

  DOI：——

  日期：——
• Synthesis and biological evaluation of a novel class of rofecoxib analogues as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs)
  作者：Qiao-Hong Chen、P.N. Praveen Rao、Edward E. Knaus

  DOI：10.1016/j.bmc.2006.07.047

  日期：2006.12

  A group of 4-(4-methanesulfonylphenyl)-3-phenyl-2(5H)furanones possessing an acetyl, 3-oxobut-1-ynyl, [hydroxyl(or alkoxy)imino]alkyl, [hydroxyl(or alkoxy)imino]alkynyl, and N-alkoxy(or N-phenoxy)carbonyl-N-hydroxy-N-ethylamino substituents at the para-position of the C-3 phenyl ring of rofecoxib were synthesized. This group of compounds was designed for evaluation as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs) that exhibit in vivo anti-inflammatory and analgesic activities. In vitro COX-1/COX-2, and 5-LOX/15-LOX, isozyme inhibition structure-activity relationships identified 3-[4-(1-hydroxyimino)ethylphenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (17a) having an optimal combination of COX-2 (COX-2 IC50 = 1.4 microM; COX-2 SI > 71), and 5-LOX and 15 LOX (5-LOX IC50 = 0.28 microM; 15-LOX IC50 = 0.32 microM), inhibitory effects. It was also discovered that 3-[4-(3-hydroxyiminobut-1-ynyl)phenyl]-4-(4-methanesulfonylphenyl)-2(5H)furanone (18a) possesses dual COX-2 (IC50 = 2.7 microM) and 5-LOX (IC50 = 0.30 microM) inhibitor actions. Further in vivo studies employing a rat carrageenan-induced paw edema model showed that the oxime compounds (17a, 18a) were more potent anti-inflammatory agents than the 5-LOX inhibitor caffeic acid, and 15-LOX inhibitor nordihydroguaiaretic acid (NDGA), but less potent than the selective COX-2 inhibitor celecoxib. The results of this investigation showed that incorporation of a para-oxime moiety on the C-3 phenyl ring of rofecoxib provides a suitable template for the design of dual inhibitors of the COX and LOX enzymes.