4,4,4-三氟-1-(4-苯基苯基)丁烷-1,3-二酮 | 581-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,4,4-三氟-1-(4-苯基苯基)丁烷-1,3-二酮
• 中文别名: 1-(4-联苯基)-4,4,4-三氟-1,3-丁二酮
• 英文名称: 1-([1,1'-biphenyl]-4-yl)-4,4,4-trifluorobutane-1,3-dione
• 英文别名: 1-(4-phenylphenyl)-4,4,4-trifluorobutane-1,3-dione；4,4,4-trifluoro-1-(biphenylyl-4)-1,3-butanedione；1-biphenyl-4-yl-4,4,4-trifluoro-butane-1,3-dione；1-Biphenyl-4-yl-4,4,4-trifluor-butan-1,3-dion；4,4,4-trifluoro-1-(4-phenylphenyl)butane-1,3-dione
• CAS: 581-83-9
• 化学式: C₁₆H₁₁F₃O₂
• 分子量: 292.257
• InChiKey: ZLQXJKTXGNVKQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4,4,4-三氟-1-(4-苯基苯基)丁烷-1,3-二酮 在 盐酸 、 platinum(IV) oxide 、 氢气 作用下， 以 乙醇 为溶剂， 生成 4-(5-biphenyl-4-yl-3-trifluoromethyl-pyrazol-1-yl)-phenylamine
  参考文献：
  名称：

  Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus

  摘要：

  Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.018
• 作为产物：
  描述：

  联苯单乙酮 、 三氟乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以80%的产率得到4,4,4-三氟-1-(4-苯基苯基)丁烷-1,3-二酮
  参考文献：
  名称：

  用于塞来昔布和其他环氧合酶抑制剂合成的集成连续流微全超快过程系统（μ-TUFPS）

  摘要：

  集成连续制造已成为快速制造活性药物成分（API）的有前途的设备。我们在此报告了一种新设计的连续流微量总工艺系统平台，用于快速生产塞来昔布（一种选择性的非甾体类抗炎药）。通常已经证明该方法可用于合成几种烷基和芳基取代的吡唑。为了最大程度地减少潜在的反应中间体/产物的繁琐后处理过程，我们开发了一种连续流萃取和分离平台，以进行整个反应序列，从而缩短了停留时间，并获得了良好的收率。本方法进一步扩展到COX-2相关API的克级合成，即。塞来昔布，在连续流动过程中。

  DOI：

  10.1021/acs.oprd.9b00212

文献信息

• First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones
  作者：Stefan Büttner、Abdolmajid Riahi、Ibrar Hussain、Mirza A. Yawer、Mathias Lubbe、Alexander Villinger、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.12.076

  日期：2009.3

  A variety of functionalized 5-aryl-3-(trifluoromethyl)phenols were prepared by the first TiCl4-mediated [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-aryl-3-trimethylsilyloxy-1-trifluoromethyl-2-en-1-ones.

  通过第一个TiCl 4介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯与3-芳基-3的[3 + 3]环缩合反应，制备了各种官能化的5-芳基-3-（三氟甲基）苯酚。-三甲基甲硅烷氧基-1-三氟甲基-2-烯-1-酮。
• One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process
  作者：Daniel J. Leng、Conor M. Black、Graham Pattison

  DOI：10.1039/c5ob02468d

  日期：——

  Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design.

  二氟甲基酮是一类研究不足的酮类化合物，具有作为材料和药物设计的有用构建块的巨大潜力。
• A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis
  作者：Balaji S. Kale、Hsin-Fu Lee、Rai-Shung Liu

  DOI：10.1002/adsc.201600980

  日期：2017.2.2

  aryl diazo ketones through two new reaction sequences involving initial gold‐catalyzed cyclization of 1,6‐enynes with diazo species, followed by rhodium‐catalyzed skeletal rearrangement of the resulting 3‐cyclopropyl‐2‐en‐1‐ones. In most instances the rhodium‐catalyzed reactions afforded cyclopentene derivatives whereas several n‐alkyl‐ or ortho‐substituted phenyl ketones delivered seven‐membered oxacycles

  这项工作报告了通过两个新的反应序列，从1,6-炔烃和芳基重氮酮构建环戊烯核，这两个反应序列涉及最初的金催化的1,6-炔烃与重氮物质的环化反应，然后铑催化的所得3的骨架重排。 -cyclopropyl-2-en-1个。在大多数情况下，铑催化的反应提供了环戊烯衍生物，而几种正烷基或邻位取代的苯基酮则提供了七元的氧杂环。一个合理的机制为这两种截然不同的产品提供了理论依据。
• [EN] A CONTINUOUS FLOW MICRO-TOTAL PROCESS SYSTEM FOR PREPARATION OF CELECOXIB AND ANALOGS THEREOF<br/>[FR] MICRO-SYSTÈME DE TRAITEMENT TOTAL À FLUX CONTINU POUR LA PRÉPARATION DU CÉLÉCOXIB ET D'ANALOGUES DE CELUI-CI
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2020157771A1

  公开（公告）日：2020-08-06

  The present invention relates to preparation of pyrazoles. This invention further relates to a continuous flow micro-total process system for preparation of celecoxib, a COX-2 selective non-steroidal anti-inflammatory drug, and analogs thereof.

  本发明涉及吡唑类化合物的制备。该发明还涉及一种用于制备选择性COX-2非甾体抗炎药Celecoxib及其类似物的连续流微总过程系统。
• Fluorotrifluoromethyl Group Installation: Tetrasubstituted Tertiary Stereocenters Containing C–F and C–CF₃ Bonds via Copper-Mediated Allylic Substitution
  作者：Yingling Zhang、Nils Raugh、Ulrich Koert

  DOI：10.1021/acs.orglett.3c02032

  日期：2023.8.4

  obtained from secondary 3-fluoro-3-trifluoromethyl allylic phosphates by a copper(I)-mediated allylic substitution reaction using Grignard reagents. The reaction features a broad substrate scope, high γ-regioselectivity, and excellent (E)-stereoselectivity. Two examples of chirality transfer from enantiopure secondary fluorine-substituted allylic phosphates to the corresponding scalemic products indicate

  含有氟三氟甲基 (FTF) 基序的四取代三级中心是通过使用格氏试剂的铜 (I) 介导的烯丙基取代反应从仲 3-氟-3-三氟甲基烯丙基磷酸酯获得的。该反应具有广泛的底物范围、高γ-区域选择性和优异的( E )-立体选择性。从对映体纯仲氟取代的烯丙基磷酸酯到相应的鳞片产物的手性转移的两个例子表明了安装 FTF 立体中心的方法的立体选择性潜力。

表征谱图