2-methoxy-1-(3-(trifluoromethyl)phenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-1-(3-(trifluoromethyl)phenyl)ethanone
• 英文别名: 2-methoxy-1-(3-(trifluoromethyl)phenyl)ethan-1-one；2-Methoxy-1-[3-(trifluoromethyl)phenyl]ethan-1-one；2-methoxy-1-[3-(trifluoromethyl)phenyl]ethanone
• 化学式: C₁₀H₉F₃O₂
• mdl: MFCD17015624
• 分子量: 218.175
• InChiKey: BCTBZMLZCLEMAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 dipotassium hydrogenphosphate 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 2-methoxy-1-(3-(trifluoromethyl)phenyl)ethanone
  参考文献：
  名称：

  与烷氧基自由基形成分子间 C-O 键：羰基化合物的光氧化还原催化 α-烷氧基化

  摘要：

  由于烷氧基 (RO·) 自由基的高反应性及其容易发生 β 断裂或氢原子转移 (HAT) 反应的倾向，几乎没有描述涉及 RO· 自由基的分子间烷氧基化。我们在此首次报道了甲硅烷基烯醇醚对烷氧基自由基的有效分子间捕获。这种光氧化还原介导的协议能够将结构简单和更复杂的烷氧基引入范围广泛的酮和酰胺中。

  DOI：

  10.1021/acs.orglett.1c03444

文献信息

• Process for producing 4-substituted benzopyran derivatives
  申请人：Central Glass Company, Limited

  公开号：US20030109574A1

  公开（公告）日：2003-06-12

  The present invention relates to a first process for producing a 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-carboxylic acid. The first process includes the steps of (a) reacting a 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-one with a perfluoroalkanesulfonic acid anhydride in the presence of a base, thereby obtaining a perfluoroalkanesulfonic 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-yl ester; and (b) reacting the benzopyranyl ester with carbon monoxide in the presence of a palladium complex compound and a base, thereby obtaining the carboxylic acid. The present invention further relates to a second process for producing a 2-hydroxy-5-(perfluoroalkyl)acetophenone, which can be a raw material for producing the carboxylic acid. The second process includes the steps of (c) reacting a 4-(perfluoroalkyl)alkoxybenzene with acetic anhydride or an acyl halide in the presence of a Lewis acid, thereby obtaining a 2-alkoxy-5-(perfluoroalkyl)acetophenone; and (d) dealkylating the 2-alkoxy-5-(perfluoroalkyl)acetophenone by a dealkylating agent.

  本发明涉及一种用于生产2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-羧酸的第一方法。该第一方法包括以下步骤：(a)在碱的存在下，将2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-酮与全氟烷基磺酸酐反应，从而获得全氟烷基磺酸酯化的2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-基酯；(b)在钯络合物和碱的存在下，将苯并吡啶酯与一氧化碳反应，从而获得羧酸。本发明还涉及一种用于生产2-羟基-5-(全氟烷基)苯乙酮的第二方法，该化合物可用作生产羧酸的原料。该第二方法包括以下步骤：(c)在Lewis酸的存在下，将4-(全氟烷基)烷氧基苯与乙酸酐或酰卤反应，从而获得2-烷氧基-5-(全氟烷基)苯乙酮；(d)通过脱烷基试剂脱烷基化2-烷氧基-5-(全氟烷基)苯乙酮。
• [EN] PROCESS FOR PRODUCING TRIFLUOROMETHYL-SUBSTITUTED 2-ALKOXYACETOPHENONE DERIVATIVES<br/>[FR] PROCEDE DE PRODUCTION DE DERIVES DE 2-ALCOXYACETOPHENONE TRIFLUOROMETHYLE-SUBSTITUEE
  申请人：CENTRAL GLASS CO LTD

  公开号：WO2004014887A1

  公开（公告）日：2004-02-19

  A process for producing a brominated acetal (represented by the formula 3) includes (a) brominating a trifluoromethyl-substituted acetophenone by Br2 in the presence of an alkylene diol. It is optional to produce a trifluoromethyl-substituted 2-alkoxyacetophenone derivative (represented by the formula 9) by (b) reacting the brominated acetal with a metal alkoxide, thereby converting the brominated acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove an acetal group from the ether, thereby producing the 2-alkoxyacetophenone derivative. Alternatively, the 2-alkoxyacetophenone can be produced by (a) reacting a trifluoromethyl-substituted phenacyl halide with an acetalization agent, thereby converting the phenacyl halide into an acetal; (b) reacting the acetal with a metal alkoxide, thereby converting the acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove the acetal group from the ether.

  生产溴代缩醛（化学式3）的过程包括：（a）在烷基二醇存在下，用Br2对三氟甲基取代的乙酰苯甲酮进行溴化。可以通过以下步骤制备三氟甲基取代的2-烷氧基乙酰苯甲酮衍生物（化学式9）：（b）将溴代缩醛与金属烷氧化物反应，将溴代缩醛转化为醚；（c）在酸催化剂存在下水解醚，从而从醚中去除缩醛基，从而制备2-烷氧基乙酰苯甲酮衍生物。或者，可以通过以下步骤制备2-烷氧基乙酰苯甲酮：（a）将三氟甲基取代的苯甲酰卤与缩醛化试剂反应，将苯甲酰卤转化为缩醛；（b）将缩醛与金属烷氧化物反应，将缩醛转化为醚；（c）在酸催化剂存在下水解醚，从而从醚中去除缩醛基。
• Electrochemical Radical Reactions of Enol Acetates and Free Alcohols Directly Access to α-Alkoxylated Carbonyl Compounds
  作者：Fan Wu、Yu Guo、Zihao Ren、Zixuan Chen、Xiaoqin Liu、Chang Wang、Liangce Rong

  DOI：10.1021/acs.joc.3c00635

  日期：2023.7.7

  The efficient intermolecular alkoxylation reactions of various enol acetates and different alcohols are developed in the electrochemical process for the first time. Enol acetates derived from either aromatic, alkyl, or alicyclic ketones, and abundant free alcohols directly used in this synthetic strategy, make this transformation very valuable in synthesis and application in the future.

  首次在电化学过程中开发了各种烯醇乙酸酯和不同醇的高效分子间烷氧基化反应。衍生自芳香族、烷基或脂环族酮的烯醇乙酸酯，以及直接用于该合成策略的丰富的游离醇，使得这种转化在未来的合成和应用中非常有价值。
• Process for producing 4-sustituted benzopyran derivatives
  申请人：Central Glass Company, Limited

  公开号：EP1298129A2

  公开（公告）日：2003-04-02

  The present invention relates to a first process for producing a 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-carboxylic acid. The first process includes the steps of (a) reacting a 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-one with a perfluoroalkanesulfonic acid anhydride in the presence of a base, thereby obtaining a perfluoroalkanesulfonic 2,2-bis(fluoromethyl)-6-(perfluoroalkyl)-2H-1-benzopyran-4-yl ester; and (b) reacting the benzopyranyl ester with carbon monoxide in the presence of a palladium complex compound and a base, thereby obtaining the carboxylic acid. The present invention further relates to a second process for producing a 2-hydroxy-5-(perfluoroalkyl) acetophenone, which can be a raw material for producing the carboxylic acid. The second process includes the steps of (c) reacting a 4-(perfluoroalkyl)alkoxybenzene with acetic anhydride or an acyl halide in the presence of a Lewis acid, thereby obtaining a 2-alkoxy-5- (perfluoroalkyl)acetophenone; and (d) dealkylating the 2-alkoxy-5-(perfluoroalkyl) acetophenone by a dealkylating agent.

  本发明涉及生产 2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-羧酸的第一种工艺。第一种工艺包括以下步骤：(a) 在碱存在下，使 2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-酮与全氟烷基磺酸酐反应，从而得到全氟烷基磺酸 2,2-双(氟甲基)-6-(全氟烷基)-2H-1-苯并吡喃-4-基酯；(b) 在钯络合物和碱存在下，使苯并呋喃基酯与一氧化碳反应，从而得到羧酸。本发明进一步涉及生产 2-羟基-5-(全氟烷基)苯乙酮的第二种工艺，该苯乙酮可作为生产羧酸的原料。第二种工艺包括以下步骤：(c) 在路易斯酸存在下，使 4-(全氟烷基)烷氧基苯与乙酸酐或酰基卤反应，从而得到 2-烷氧基-5-(全氟烷基)苯乙酮；(d) 用脱烷基剂使 2-烷氧基-5-(全氟烷基)苯乙酮脱烷基。
• Process for producing trifluoromethyl- substituted 2- alkoxyacetophenone derivatives
  申请人：Ishii Akihiro

  公开号：US20050171363A1

  公开（公告）日：2005-08-04

  A process for producing a brominated acetal (represented by the formula 3) includes (a) brominating a trifluoromethyl-substituted acetophenone by Br 2 in the presence of an alkylene diol. It is optional to produce a trifluoromethyl-substituted 2-alkoxyacetophenone derivative (represented by the formula 9) by (b) reacting the brominated acetal with a metal alkoxide, thereby converting the brominated acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove an acetal group from the ether, thereby producing the 2-alkoxyacetophenone derivative. Alternatively, the 2-alkoxyacetophenone can be produced by (a) reacting a trifluoromethyl-substituted phenacyl halide with an acetalization agent, thereby converting the phenacyl halide into an acetal; (b) reacting the acetal with a metal alkoxide, thereby converting the acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove the acetal group from the ether.

  生产溴化缩醛（由式 3 表示）的工艺包括 (a) 用 Br 2 溴化三氟甲基取代的苯乙酮。可选择通过以下方法生产三氟甲基取代的 2-烷氧基苯乙酮衍生物（由式 9 表示）：(b) 使溴化缩醛与金属氧化烷反应，从而将溴化缩醛转化为醚；(c) 在酸催化剂存在下水解醚，从醚中除去缩醛基团，从而生产 2-烷氧基苯乙酮衍生物。或者，2-烷氧基苯乙酮可以通过以下方法制得：(a) 使三氟甲基取代的苯酰卤与缩醛剂反应，从而将苯酰卤转化为缩醛；(b) 使缩醛与金属烷氧基反应，从而将缩醛转化为醚；(c) 在酸催化剂存在下水解醚，以除去醚中的缩醛基团。