2-苄基-4,4,4-三氟-3-氧代丁酸乙酯 | 118642-72-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 2-苄基-4,4,4-三氟-3-氧代丁酸乙酯
• 英文名称: benzyl-2 trifluoroacetylacetate d'ethyle
• 英文别名: Ethyl 2-benzyl-4,4,4-trifluoro-3-oxobutanoate
• CAS: 118642-72-1
• 化学式: C₁₃H₁₃F₃O₃
• mdl: MFCD08447599
• 分子量: 274.24
• InChiKey: YDYTURLXGFPZQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-苄基-4,4,4-三氟-3-氧代丁酸乙酯 在 水 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到1,1,1-三氟-4-苯基-2-丁酮
  参考文献：
  名称：

  Alkylation du trifluoroacetylacetate d'ethyle methode generale d'acces aux trifluoromethylcetones. 2ème Partie: alkylations indirects du TFAAE

  摘要：

  DOI：

  10.1016/s0022-1139(00)82804-3
• 作为产物：
  描述：

  ethyl (3E)-2-benzyl-3-(dimethylhydrazinylidene)-4,4,4-trifluorobutanoate 生成 2-苄基-4,4,4-三氟-3-氧代丁酸乙酯
  参考文献：
  名称：

  CHARPENTIER-MORIZE, MICHELINE;AUBERT, CORINNE;LANGLOIS, BERNARD;BEGUE, JE+

  摘要：

  DOI：

文献信息

• [EN] BENZOXAZEPINES AS INHIBITORS OF MTOR AND THEIR USE TO TREAT CANCER<br/>[FR] BENZOXAZÉPINES EN TANT QU'INHIBITEURS DE MTOR ET LEUR UTILISATION POUR TRAITER LE CANCER
  申请人：EXELIXIS INC

  公开号：WO2010135568A1

  公开（公告）日：2010-11-25

  The invention is directed to inhibitors of mTOR and pharmaceutically acceptable salts or solvates thereof, as well as methods of using them. The inhibitors are generally of structural formula : wherein the combination of R1 and R2 are as defined herein, and pharmaceutically acceptable salts thereof.

  这项发明涉及 mTOR 的抑制剂及其药用盐或溶剂，以及它们的使用方法。这些抑制剂通常具有以下结构式：其中 R1 和 R2 的组合如本文所定义，并且其药用盐。
• Efficient Procedure to 4-Carbethoxy-3-Trifluoro Methylcyclohex-2-Enone and 4-Alkylated Derivatives
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Anukwadey Dogbeavou

  DOI：10.1080/00397919208019256

  日期：1992.2

  Abstract The 4-carbethoxy-3-trifluoromethylcyclohex-2-enone 1a was prepared in one-pot procedure in 90 % yield, from ethyl trifluoroacetoacetate (ETFAAE) and methylvinyl ketone. This reaction has been extended to alkylated ethyl trifluoroacetoacetate.

  摘要 4-carbethoxy-3-trifluoromethylcyclohex-2-enone 1a 是由三氟乙酰乙酸乙酯 (ETFAAE) 和甲基乙烯基酮以 90% 的一锅法制备的。该反应已扩展到烷基化的三氟乙酰乙酸乙酯。
• Alkylation of ethyl 4,4,4-trifluoroacetoacetate. First example of a reversible O-alkylation process leading to C-alkylation
  作者：Jean-Pierre Bégué、Micheline Charpentier-Morize、Gérard Née

  DOI：10.1039/c39890000083

  日期：——

  polar solvents the ratio of O vs. C alkylation products of ethyl 4,4,4-trifluoroacetoacetate (ETFAA)can be dependent on reaction time; in hexamethylphosphoric triamide (HMPA) or acetone, the SN2 cleavage of enol ethers of ETFAA with sodium iodide was observed with concomitant formation of the sodium enolate and the corresponding iodides, and in the case of an activated iodide the mono- and di-alkylation

  在非质子极性溶剂中，4,4,4-三氟乙酰乙酸乙酯（ETFAA）的O与C烷基化产物之比取决于反应时间。在六甲基磷酸三酰胺（HMPA）或丙酮中，观察到ETFAA的烯醇醚与碘化钠的S N 2裂解，同时形成了烯醇酸钠和相应的碘化物，在活化碘化物的情况下，单和二碘化物定量得到烷基化产物。
• Studies on New Acidic Azoles as Glucose-Lowering Agents in Obese, Diabetic db/db Mice
  作者：Kenneth L. Kees、Thomas J. Caggiano、Kurt E. Steiner、John J. Fitzgerald、Michael J. Kates、Thomas E. Christos、John M. Kulishoff、Robin D. Moore、Michael L. McCaleb

  DOI：10.1021/jm00004a008

  日期：1995.2

  Bioisosteric substitution was used as a tool to generate several new structural alternatives to the thiazolidine-2,4-dione and tetrazole heterocycles as potential antidiabetic agents. Among the initial leads that emerged from this strategy, a family of acidic azoles isoxazol-3- and -5-ones and a pyrazol-3-one, showed significant plasma glucose-lowering activity (17-42% reduction) in genetically obese, diabetic db/db mice at a dose of 100 mg/kg/day x 4. Structure-activity relationship studies determined that 5-alkyl-4-(arylmethyl)pyrazol-3-ones, which exist in solution as aromatic enol/iminol tautomers, were the most promising new class of potential antidiabetic agent (32-45% reduction at 20 mg/kg/d x 4). Included in this work are convenient syntheses for several types of acidic azoles that may find use as new acidic bioisosteres in medicinal chemistry such as the antidiabetic lead 5-(trifluoromethyl)pyrazol-3-one (hydroxy tautomer) and aza homologs of the pyrazolones, 1,2,3-triazol-5-ones (hydroxy tautomer) and 1,2,3,4-tetrazol-5-one heterocycles. log P and pK(a) data for 15 potential acidic bioisosteres, all appended to a 2-naphthalenylmethyl residue so as to maintain a similar distance between the acidic hydrogen and arene nucleus, are presented. This new data set allows comparison of a wide variety of potential acid mimetics (pK(a) 3.78-10.66; log P -0.21 to 2.76) for future drug design.
• Nonpeptide endothelin antagonists: from lower affinity pyrazol-5-ols to higher affinity pyrazole-5-carboxylic acids
  作者：Jidong Zhang、Stanislas Didierlaurent、Michel Fortin、Dominique Lefrançois、Eric Uridat、Jean Paul Vevert

  DOI：10.1016/s0960-894x(00)00232-8

  日期：2000.6

  Random screening of compounds in endothelin receptor (ETA and ETB) binding assays led to the discovery of a new class of pyrazol-5-ol ligands. Characterization of structural features crucial for binding activities of these pyrazol-5-ols, by structure-activity-relationship (SAR) studies, allowed us to design a novel class of pyrazole-5-carboxylic acids as more potent ET antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.