二氟苯基乙酸甲酯 | 56071-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二氟苯基乙酸甲酯
• 英文名称: methyl 2,2-difluoro-2-phenylacetate
• 英文别名: methyl phenyldifluoroacetate；difluorophenylacetic acid methyl ester
• CAS: 56071-96-6
• 化学式: C₉H₈F₂O₂
• mdl: MFCD12031803
• 分子量: 186.158
• InChiKey: VWHZGGBEUOYQJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二氟苯基乙酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2,2-Difluoro-1-methoxy-2-phenylethanol
  参考文献：
  名称：

  Conversion of .alpha.-Keto Esters into .beta.,.beta.-Difluoro-.alpha.-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors

  摘要：

  The preparation of a series of beta,beta-difluoro-alpha-keto esters and corresponding acids RCF(2)COCO(2)R' (R = Me, Et; i-Pr, Bn, and Ph; R' = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an alpha,alpha-difluoro ester from an alpha-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and alpha-hydroxy ester difluorinated intermediates. This method provides an easy route to beta,beta-difluoro-alpha-keto esters and corresponding acids, via ''formal'' insertion of a difluoromethylene group between the R substituent and the alpha-carbonyl group of a generic alpha-keto ester.

  DOI：

  10.1021/jo00121a040
• 作为产物：
  描述：

  苯乙酸甲酯 在 manganese(II) bromide 、 双(三甲基硅烷基)氨基钾 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 二氟苯基乙酸甲酯
  参考文献：
  名称：

  Synthesis and Biological Properties of Novel Fluoroprostaglandin Derivatives: Highly Selective and Potent Agonists for Prostaglandin Receptors

  摘要：

  将合成新的7,7-二氟前列环素和15-去氧-15,15-二氟-PGF2?衍生物的结果将被展示。这些化合物表现出对前列腺素受体的高亲和力和强效的生物活性。

  DOI：

  10.2533/000942904777678073

文献信息

• [EN] 1,5-DISTRIBUTED PYRROLID-2-ONE DERIVATIVES FOR USE AS EP4 RECEPTOR AGONISTS IN THE TEATMENT OF EYE DISEASES SUCH AS GLAUCOMA<br/>[FR] DERIVES DE PYRROLID-2-ONE 1,5 DISUBSTITUES UTILISES COMME AGONISTES DE RECEPTEUR EP4 POUR TRAITER DES MALADIES OCULAIRES TELLES QUE LE GLAUCOME
  申请人：MERCK FROSST CANADA INC

  公开号：WO2003103772A1

  公开（公告）日：2003-12-18

  This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors of formula (I), their use or a formulation thereof in the treatment of glaucoma and other conditions which are related to elevated intraocular pressure in the eye of the patient.

  这项发明涉及强效选择性的前列腺素E2受体EP4亚型的激动剂，其化学公式为（I），以及它们在治疗青光眼和其他与患者眼睛内压升高相关的病症中的使用或其制剂。
• Borosilicate Activation of (Difluoroiodo)toluene in the<i>gem</i>-Difluorination of Phenyldiazoacetate Derivatives
  作者：Geoffrey S. Sinclair、Richard Tran、Jason Tao、W. Scott Hopkins、Graham K. Murphy

  DOI：10.1002/ejoc.201600773

  日期：2016.9

  A combined experimental and computational investigation was conducted to identify a mild and effective Lewis-acidic activator for TolIF2 in the gem-difluorination of diazo compounds. Computationally, borosilicate, a common constituent of laboratory glassware, was found to spontaneously activate TolIF2, and an extensive experimental survey confirmed borosilicate as the most effective activator to date

  进行了一项结合实验和计算研究，以在重氮化合物的双氟化过程中为 TolIF2 鉴定一种温和且有效的路易斯酸性活化剂。通过计算，发现实验室玻璃器皿的常见成分硼硅酸盐会自发激活 TolIF2，并且广泛的实验调查证实硼硅酸盐是迄今为止最有效的激活剂。实现这种硼硅酸盐活化反应的关键是使用高纯度 TolIF2，它是通过可重现的多克级合成制备的。
• The effect of substituents and operating conditions on the electrochemical fluorination of alkyl phenylacetates in Et3N·4HF medium
  作者：N. Ilayaraja、A. Manivel、D. Velayutham、M. Noel

  DOI：10.1016/j.jfluchem.2007.10.007

  日期：2008.3

  Selective electrochemical fluorination of alkyl phenylacetates (Ph–CH2–COOR, where R is methyl, ethyl, n-propyl, n-butyl, i-propyl and sec-butyl) under galvanostatic conditions were reported in Et3N·4HF medium. Preparative electrolysis experiments were carried out both in pre-electrolysed dry Et3N·4HF and the same electrolyte medium without pre-electrolysis. Very little hydrolysed fluorinated products

  烷基乙酸苯的选择性电化学氟化（PH-CH 2 -COOR，其中R为甲基，乙基，Ñ丙基，Ñ丁基，我-丙基和仲-丁基）恒电流条件下被报告在Et 3 N·4HF平台。在预电解干燥的Et 3 N·4HF和相同的电解质介质中进行了预电解实验，没有进行预电解。在预电解介质中几乎没有得到水解的氟化产物，其中从Et 3获得了大量导致氟化苯乙酸的水解产物。N·4HF不需预电解。在最佳实验条件下，可以实现高达87％的单氟酯选择性。获得的其他主要副产物是二氟烷基苯乙酸酯，一氟和二氟苯乙酸。在最初的阳离子自由基电氧化形成后，水解似乎是由质子的互变异构转化引发的。已采用19 F和1 H NMR光谱鉴定在电氧化过程中形成的次要成分。
• Aryl halides as convenient precursors of electrogenerated bases. Efficient syntheses of β-oxo nitriles or esters by coupling active-hydrogen groups with esters
  作者：Rachid Barhdadi、Jacques Gal、Monique Heintz、Michel Troupel

  DOI：10.1039/c39920000050

  日期：——

  In an undivided cell fitted with a sacrifical anode and a nickel cathode on which cadmium had been deposited, the electroreduction of aromatic halides affords a strong base which allows the effective synthesis of β-oxo nitriles or β-oxo esters from the coupling of active-hydrogen compounds with esters.

  在装有牺牲阳极和沉积了镉的镍阴极的未分割电池中，芳香卤化物的电还原提供了强碱，从而能够通过活性氢化合物与酯的耦合，实现β-氧代腈或β-氧代酯的有效合成。
• Aryl halides as precursors of electrogenerated bases. Utilization in coupling reactions of acetonitrile with various electrophilic compounds.
  作者：Rachid Barhdadi、Jacques Gal、Monique Heintz、Michel Troupel、Jacques Périchon

  DOI：10.1016/s0040-4020(01)81874-3

  日期：1993.6

  alternative to classical cyanomethylation is possible by using electrogenerated bases (EGBs), obtained by electroreduction of aryl halides in an undivided cell fitted with a cadmium coated cathode and a sacrificial magnesium anode. Acetonitrile is used both as solvent and as hydrogen-active compound. A coupling reaction with various electrophilic compounds was carried out. When the electrophilic compound

  通过使用电生成的碱（EGB），可以替代传统的氰基甲基化，这是通过在配有镉涂层阴极和牺牲镁阳极的未分隔电池中对芳基卤化物进行电还原而获得的。乙腈既用作溶剂又用作氢活性化合物。与各种亲电子化合物进行偶联反应。当从电解开始就存在亲电子化合物时，获得了预期的与氰基甲基阴离子的偶联产物。如果仅在芳基卤化物完全电解之后才添加亲电化合物，则观察到氰基甲基阴离子的二聚化和二聚体阴离子与亲电化合物之间的偶联反应。