(2-trifluoromethylphenyl)propynoic acid | 2806-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-trifluoromethylphenyl)propynoic acid
• 英文别名: 3-(2-trifluoromethylphenyl)prop-2-ynoic acid；(2-Trifluormethyl-phenyl)-propinsaeure；(2-trifluoromethylphenyl)propiolic acid；3-(2-(Trifluoromethyl)phenyl)propiolic acid；3-[2-(trifluoromethyl)phenyl]prop-2-ynoic acid
• CAS: 2806-31-7
• 化学式: C₁₀H₅F₃O₂
• 分子量: 214.144
• InChiKey: FLVZIGGVBAYIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-trifluoromethylphenyl)propynoic acid 在 氯化亚砜 作用下， 以 乙醇 、 苯 为溶剂， 反应 7.0h， 生成 (Z)-3-Carbamimidoylsulfanyl-N-phenyl-3-(2-trifluoromethyl-phenyl)-acrylamide; compound with toluene-4-sulfonic acid
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3
• 作为产物：
  描述：

  Ethyl 3-[2-(trifluoromethyl)phenyl]-2-propynoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以487 mg的产率得到(2-trifluoromethylphenyl)propynoic acid
  参考文献：
  名称：

  Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ (PPARγ)-selective antagonists based on the helix12-folding inhibition hypothesis

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhibition hypothesis, in combination with our previously determined X-ray crystal structure of PPAR gamma agonist MEKT-21 (6) complexed with the PPAR gamma ligand-binding domain, to design and develop a potent phenylalkynyl amide-type PPAR gamma antagonist 9i, focusing initially on pinpoint structural modification of the propanoic acid moiety of 6. Since 9i retained very weak, but distinct, PPAR gamma agonist activity, we next modified the distal benzene ring of 9i, aiming to delete the residual PPAR gamma agonist activity while retaining the antagonist activity. Introduction of a chlorine atom at the 2-position of the distal benzene ring afforded 9p, which exhibited potent, PPAR gamma-selective full antagonist activity without detectable agonist activity. We found that 9p stabilized the corepressor PPAR gamma complex and suppressed basal PPAR gamma activity. This compound showed anti-adipogenesis activity at the cellular level. This agonist antagonist switching concept based on the H12-folding inhibition hypothesis should also be applicable for designing other classes of PPAR gamma full antagonists. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.017

文献信息

• [DE] SUBSTITUIERTE 1-PROPIOLYL-PIPERAZINE MIT AFFINITÄT FÜR DEN MGLUR5 REZEPTOR ZUR BEHANDLUNG VON SCHMERZZUSTÄNDEN<br/>[EN] SUBSTITUTED 1-PROPIOLYLPIPERAZINES HAVING AN AFFINITY FOR THE MGLUR5 RECEPTOR IN ORDER TO TREAT PAINFUL CONDITIONS<br/>[FR] 1-PROPIOLYLPIPERAZINES SUBSTITUEES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR MGLUR5, UTILISEES POUR LE TRAITEMENT DE DOULEURS
  申请人：GRUENENTHAL GMBH

  公开号：WO2006002981A1

  公开（公告）日：2006-01-12

  Die vorliegende Erfindung betrifft substituierte 1-Propiolyl-piperazine gemäss Formel (I), Verfahren zu ihrer Herstellung, Arzneimittel enthaltend diese Verbindungen sowie deren Verwendung zur Herstellung von Arzneimitteln. (I), worin X für N oder C-R2 steht und n einem Wert zwischen 0-8 entspricht.

  这项发明涉及按照式(I)的取代的1-丙炔基哌嗪，其制备方法，包含这些化合物的药物以及它们用于制备药物的用途。(I)，其中X代表N或C-R2，n为0-8之间的值。
• Alkynyl triazenes enable divergent syntheses of 2-pyrones
  作者：Jin-Fay Tan、Carl Thomas Bormann、Kay Severin、Nicolai Cramer

  DOI：10.1039/d1sc02583j

  日期：——

  The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alkynyl triazenes promote a smooth addition of propiolic acids across the triple bond. Addition of catalytic amounts of silver salt induces cyclization

  2-吡喃酮基序经常出现在生物活性天然产物中，并被认为是合成中间体。然而，只有少数方法允许对该相关杂环进行多样化的官能团修饰。 1-炔基三氮烯的独特性质促进丙炔酸在三键上顺利加成。添加催化量的银盐诱导环化成2-吡喃酮。根据反应温度，选择性地形成6-三氮烯基或5-三氮烯基2-吡喃酮。随后，三氮烯基单元在一锅法中被各种有价值的基团取代，产生例如 2-氟吡喃酮。这种取代是通过有趣的 1,5-羰基转位发生的。此外，三氮烯基可作为后续狄尔斯-阿尔德环加成的无痕活化基团，并作为稀有稠合氨基吡唑吡喃酮杂环的构成单元。
• Substituted 1-propiolylpiperazine compounds, their preparation and use
  申请人：Kuhnert Sven

  公开号：US20070112011A1

  公开（公告）日：2007-05-17

  Substituted 1-propiolylpiperazine compounds corresponding to formula I in which X denotes N or C—R 2 , and n is an integer from 0 to 8, a method for producing such substituted 1-propiolylpiperazine compounds, pharmaceutical compositions containing such substituted 1-propiolylpiperazine compounds, and the use of such substituted 1-propiolylpiperazine compounds for modulating mGluR5 receptor activity or for treating or inhibiting pain and various other conditions, especially conditions at least partly mediated by the mGluR5 receptor.

  将符合公式I的1-丙炔基哌嗪化合物替代为X代表N或C—R，n为0至8的整数，一种生产这种替代的1-丙炔基哌嗪化合物的方法，含有这种替代的1-丙炔基哌嗪化合物的药物组合物，以及利用这种替代的1-丙炔基哌嗪化合物调节mGluR5受体活性或用于治疗或抑制疼痛和其他各种病症，特别是至少部分由mGluR5受体介导的病症。
• Metal -free PhI(OAc)₂-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations
  作者：Tianyong Gao、Yawen Yang、Liangzhen Hu、Dan Luo、Xiaohui Zhang、Yan Xiong

  DOI：10.1039/d2ob02281h

  日期：——

  A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents is described. This decarboxylative C–O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic propiolic acids to give the corresponding α-acetoxy ketones. Preliminary mechanistic studies based on both DFT calculations and high-resolution

  描述了由高价碘 ( III ) 试剂介导的丙炔酸的无金属氧化脱羧反应。这种脱羧 C-O 键形成反应使用 (diacetoxyiodo) 苯和芳族、杂芳族或脂肪族丙炔酸的组合，得到相应的 α-乙酰氧基酮。基于 DFT 计算和高分辨率质谱 (HRMS) 的初步机理研究表明，反应通过脱羧作用进行，形成炔丙基碘化物中间体。该反应为现有的 α-酰氧基酮的独家合成方法提供了一种有吸引力的替代方法。
• <b>A New Method of Evaluating <b><i>ortho</i></b> σ-Constants</b>
  作者：Irvine J. Solomon、Robert. Filler

  DOI：10.1021/ja00904a042

  日期：1963.11