3-oxo-5,5-diphenylpentanoic acid ethylester | 118217-47-3

• 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: 3-oxo-5,5-diphenylpentanoic acid ethylester
• 英文别名: ethyl 3-oxo-5,5-diphenylpentanoate；ethyl 3-oxo-5,5-diphenylvalerate；β-oxo-δ-phenyl-benzene pentanoic acid ethyl ester；beta-Oxo-delta-phenyl-benzene pentanoic acid ethyl ester
• CAS: 118217-47-3
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: VEIVEIFNOREFMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  400.7±30.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  3-oxo-5,5-diphenylpentanoic acid ethylester 在 三乙烯二胺 作用下， 以 xylene 为溶剂， 反应 5.0h， 生成 4,4'-二苯基-2-丁酮
  参考文献：
  名称：

  Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel .beta.-keto amides as hypocholesterolemic agents

  摘要：

  A study of structure-activity relationships of substituted beta-ketoamide ACAT inhibitors I and II was performed. The results of this study suggest that whereas the beta-keto group was tolerated with no loss in activity, beta-hydroxy and oxime moieties led to significantly reduced activity in vitro and in vivo. The most potent inhibitor from the acyclic series (I) (11, IC50 = 0.006 muM) contained a C-13 alkyl chain. This compound reduced plasma total cholesterol by 38% and 66% at 3 and 30 mg/kg, respectively, in cholesterol-fed rats. Dimethylation alpha to the anilide core(5) and subsequent N-methylation of the amide NH (6) decreased in vitro potency significantly. It was also found that high potency was retained with inhibitors which incorporated the carbonyl into a lactam ring (II).

  DOI：

  10.1021/jm00072a014
• 作为产物：
  描述：

  3,3-二苯基丙酸 在 正丁基锂 、 氯化亚砜 作用下， 反应 24.5h， 生成 3-oxo-5,5-diphenylpentanoic acid ethylester
  参考文献：
  名称：

  Leysen; Haemers; Blanchaert, Farmaco, Edizione Pratica, 1987, vol. 42, # 11, p. 823 - 831

  摘要：

  DOI：

文献信息

• Substituted beta-ketoamide ACAT inhibitors
  申请人：Warner-Lambert Company

  公开号：US05278326A1

  公开（公告）日：1994-01-11

  Novel pharmaceutically useful compounds which lower blood cholesterol levels and are beta-ketoamides, oximes, amines, and hydroxyl derivatives thereof.

  新型药用化合物，可降低血液胆固醇水平，包括β-酮酰胺、肟、胺和其羟基衍生物。
• Synthesis of 2-Hydroxy-1-naphthoic Acid Derivatives by Oxidative Cyclization of Esters of 5-Aryl-3-oxopentanoic Acid by Mn(III) and Ce(IV) Salts
  作者：Attilio Citterio、Luca Pesce、Roberto Sebastiano、Roberto Santi

  DOI：10.1055/s-1990-26814

  日期：——

  A new synthesis of substituted 2-hydroxy-1-naphthoic acid esters and amides 4 by oxidation of 5-aryl-3-oxopentanoic acid esters or amides 1 with manganese(III) acetate or cerium(IV) ammonium nitrate has been developed, based on the intramolecular homolytic substitution by α-dicarbonylalkyl radicals generated from high-valent metal β-dicarbonyl complexes.

  通过用醋酸锰（III）或硝酸铈（IV）铵氧化 5-芳基-3-氧代戊酸酯或酰胺 1，开发了一种取代的 2-羟基-1-萘酸酯和酰胺 4 的新合成方法，其基础是由高价金属δ-²-二羰基络合物产生的δ-二羰基烷基自由基进行分子内均聚取代。
• Chemoselective Aromatic C–H Insertion of α-Diazo-β-ketoesters Catalyzed by Dirhodium(II) Carboxylates
  作者：Esdrey Rodriguez-Cárdenas、Rocío Sabala、Moisés Romero-Ortega、Aurelio Ortiz、Horacio F. Olivo

  DOI：10.1021/ol202968z

  日期：2012.1.6

  The ability of alpha-diazo-beta-ketoesters bearing a substituent on the benzylic position to undergo aromatic C-H insertion is described. Good to excellent yields of the aromatic C-H insertion products were observed with Rh-2(tpa)(4) or Rh-2(esp)(2) catalysts. This is an attractive strategy to prepare tetralins carrying a methyl group on the benzylic position, a structural motif found in several types of natural products.
• US3994915A
  申请人：——

  公开号：US3994915A

  公开（公告）日：1976-11-30
• US4042596A
  申请人：——

  公开号：US4042596A

  公开（公告）日：1977-08-16