1,1,1-trifluoro-5-(4-methoxy-phenyl)-pentan-2-one | 112298-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1,1-trifluoro-5-(4-methoxy-phenyl)-pentan-2-one
• 英文别名: 1,1,1-trifluoro-5-(4-methoxyphenyl)pentan-2-one；5-(p-methoxyphenyl)-1,1,1-trifluoropentan-2-one
• CAS: 112298-29-0
• 化学式: C₁₂H₁₃F₃O₂
• 分子量: 246.229
• InChiKey: PFAYYVBXQNMWBS-UHFFFAOYSA-N

物化性质

• 沸点：
  82 °C(Press: 0.5 Torr)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-5-(4-methoxy-phenyl)-pentan-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以86%的产率得到5-(4-methoxyphenyl)-1,1,1-trifluoropentan-2-ol
  参考文献：
  名称：

  .alpha.-Trifluoromethyl-destabilized cations. A route to 1-(trifluoromethyl)tetralins by trifluoroacetolysis of 5-aryl-1,1,1-trifluoropentan-2-ols and derivatives

  摘要：

  DOI：

  10.1021/jo00239a010
• 作为产物：
  描述：

  5-(4-methoxyphenyl)-1,1,1-trifluoropentan-2-ol 在 RuCl₂(biox)2 sodium periodate 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 以85%的产率得到1,1,1-trifluoro-5-(4-methoxy-phenyl)-pentan-2-one
  参考文献：
  名称：

  New catalytic oxidation of trifluoromethyl carbinols by a ruthenium(II) complex

  摘要：

  The first catalytic oxidation of trifluoromethyl carbinols has been accomplished by a novel ruthenium(II) complex using sodium periodate as an oxidant. Trifluoromethyl ketones were obtained under mild conditions and in excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00378-6

文献信息

• Regioselective Intramolecular Oxidation of Phenols and Anisoles by Dioxiranes Generated in Situ
  作者：Dan Yang、Man-Kin Wong、Zheng Yan

  DOI：10.1021/jo000458j

  日期：2000.6.1

  and H(2)O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective pi bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation

  已经开发了一种用于酚和茴香的区域选择性氧化的新方法，其中由酮和Oxone原位生成的二恶英类化合物以分子内方式氧化酚衍生物。一系列具有吸电子基团的酮，例如CF（3），COOMe和CH（2）Cl，通过C（2）或C（3）亚甲基连接基连接到苯酚，茴香醚或芳基环上。在CH（3）CN和H（2）O的均相溶剂系统中，苯酚衍生物1-10的氧化反应以2-55％的收率得到螺2-羟基二烯酮，而与其他取代基的存在无关（邻位Me，间位Me或Br）和芳基环的长度。提供了实验证据来支持涉及芳基环的区域选择性pi键环氧化，然后环氧化物重排和半缩酮形成的机制。
• Addition of 2-(Trimethylsilyl)thiazole to Alkyl and Aryl Perfluoroalkyl Ketones: Synthesis of Fluorinated Tertiary Alcohols and α-Hydroxy Aldehydes
  作者：Alessandro Dondoni、Alessia Boscarato、Paolo Formaglio、Jean-Pierre Bégué、Farid Benayoud

  DOI：10.1055/s-1995-3976

  日期：1995.6

  The spontaneous addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various alkyl and aryl perfluoroalkyl ketones 2 in THF at 80°C affords the corresponding tertiary alcohols 4 which by thiazolyl-to-formyl conversion are transformed into fluorinated α-hydroxy aldehydes 6. The formation of silyl enol ether side products is observed in the reaction of 2-TST 1 with alkyl ketones 2b-e.

  在 80°C 的 THF 溶液中，2-(三甲基硅基)噻唑 (2-TST, 1) 自发加成到各种烷基和芳基全氟烷基酮 2 上，得到相应的叔醇 4，通过噻唑基到甲酰基的转化，将其转化为氟化 δ。 ±-羟基醛 6. 在 2-TST 1 与烷基酮 2b-e 的反应中观察到甲硅烷基烯醇醚副产物的形成。
• Trifluoroacetylalkyl-substituted phenyl, phenol and benzoyl compounds and related methods of treatment
  申请人：SOLVAY PHARMACEUTICALS GMBH

  公开号：US20040214901A1

  公开（公告）日：2004-10-28

  Novel and known trifluoroacetyl-substituted phenyl, phenol and benzoyl compounds for the treatment and/or inhibition of obesity and of concomitant and/or secondary diseases involved therewith, in particular metabolic syndrome and cardiovascular diseases. Novel trifluoroacetyl-substituted phenyl, phenol and benzoyl compounds, pharmaceutical preparations containing them and processes for the preparation of these compounds. Also compounds acting as inhibitors of lipase, in particular pancreatic lipase.

  用于治疗和/或抑制肥胖症及其相关和/或继发疾病，特别是代谢综合征和心血管疾病的新型和已知的三氟乙酰基取代苯、苯酚和苯甲酰化合物。新型的三氟乙酰基取代苯、苯酚和苯甲酰化合物、含有它们的制药制剂以及制备这些化合物的过程。还有作为脂肪酶抑制剂，特别是胰脂肪酶抑制剂的化合物。
• Intramolecular Friedel-Crafts alkylation and chloroalkylation of 5-aryl-1,1,1-trifluoropentan-2-ones. A route to (trifluoromethyl)dihydronaphthalenes and (trifluoromethyl)tetrahydronaphthalenes
  作者：D. Bonnet-Delpon、M. Charpentier-Morize、R. Jacquot

  DOI：10.1021/jo00239a011

  日期：1988.2
• The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones
  作者：Jean Pierre Begue、Daniele Bonnet-Delpon、Dany Mesureur、Gerard Nee、Sheng Wen Wu

  DOI：10.1021/jo00040a017

  日期：1992.7

  The preparation of novel perfluoroalkyl-substituted compounds in good yields is described. This preparation involves the Wittig reaction of a phosphonium ylide with perfluoroalkyl acid derivatives. The influence of the structure of the starting alkylidenetriphenylphosphoranes, the perfluoroalkyl reagents, and the reaction conditions has been investigated. Trifluoroacetamides lead to a Z/E mixture of enamines 3. Perfluoroalkyl esters (Rf = CF3, C2F5, C3F7, C7F15, CF2Cl) lead to only the (Z)-enol ethers 8-12 when reactions are performed with NaNH2 as a base and to 1-perfluoroalkyl ketones 13-17 when reactions are performed with BuLi.