4-(4-(trifluoromethyl)phenyl)but-3-yn-1-ol | 173546-22-0

• 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: 4-(4-(trifluoromethyl)phenyl)but-3-yn-1-ol
• 英文别名: 4-[4-(Trifluoromethyl)phenyl]but-3-YN-1-OL
• CAS: 173546-22-0
• 化学式: C₁₁H₉F₃O
• 分子量: 214.187
• InChiKey: PZFMHTDMSNDETK-UHFFFAOYSA-N

物化性质

• 沸点：
  273.9±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(trifluoromethyl)phenyl)but-3-yn-1-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 4-(4-(trifluoromethyl)phenyl)butan-1-ol
  参考文献：
  名称：

  通过铑烷基氮烯 C-H 插入反选择性合成取代的 β-高脯氨酸

  摘要：

  制备了一系列具有高抗选择性的β-高脯氨酸。涉及烷基氮烯铑的分子内 C-H 插入反应是环构建的关键步骤。产品中的羧酸可以作为进一步下游转化的跳板。

  DOI：

  10.1055/a-2201-7267
• 作为产物：
  描述：

  对溴三氟甲苯 、 3-丁炔-1-醇 在 bis(η3-allyl-μ-chloropalladium(II)) 、 Tedicyp copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到4-(4-(trifluoromethyl)phenyl)but-3-yn-1-ol
  参考文献：
  名称：

  Coupling reactions of aryl bromides with 1-alkynols catalysed by a tetraphosphine/palladium catalyst

  摘要：

  cis. cis, cis-1, 2, 3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)](2) system catalyses efficiently the coupling reactions of aryl halides with a variety of alkynols such as propargy] alcohol, but-1-yn-4-ol, pent-1-yn-5-ol or hex-1-yn-6-ol. The catalyst can be used at lowloading. Higher reaction rates were observed in the presence of but-1-yn-4-ol, pent-1-yn-5-ol or hex-1-yn-6-ol than with propargy] alcohol. The protection of the alcohol functions as an ether or a silyloxy group led generally to similar or better results than the reactions performed with the unprotected alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.128

文献信息

• Tandem Regioselective Hydroformylation-Hydrogenation of Internal Alkynes Using a Supramolecular Catalyst
  作者：Weiwei Fang、Bernhard Breit

  DOI：10.1002/anie.201809073

  日期：2018.11.5

  electron‐withdrawing groups. By applying this novel catalytic system, a general protocol for the Rh‐catalysed hydroformylation‐hydrogenation of unsymmetrical internal alkynes, functionalized with a carboxylic acid, was found to furnish aliphatic aldehydes in high regio‐ and chemoselectivities. Control experiments confirm the enzyme‐like supramolecular catalyst mode of action.

  基于通过引入吸电子基团提高膦配体的π-受体能力的策略，设计了具有酰基胍基功能的新的超分子配体。通过应用这种新颖的催化系统，发现了用羧酸官能化的不对称内部炔烃进行Rh催化加氢甲酰化-加氢的通用方案，可提供具有高区域选择性和化学选择性的脂族醛。对照实验证实了类似酶的超分子催化剂的作用方式。
• Phenyl derivatives comprising an acetylene group
  申请人：Ackermann Jean

  公开号：US20060004091A1

  公开（公告）日：2006-01-05

  This invention is concerned with compounds of the formula I: wherein one of R 5 , R 6 and R 7 is and X 1 , X 2 , R 1 to R 12 , m, n and o are as defined in the description, and pharmaceutically acceptable salts and/or esters thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.

  这项发明涉及式I的化合物：其中R5、R6和R7中的一个是X1、X2、R1到R12、m、n和o如描述中所定义的，并且其药学上可接受的盐和/或酯。该发明还涉及含有这种化合物的药物组合物，以及用于治疗和/或预防由PPARδ和/或PPARα激动剂调节的疾病的方法。
• Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2‐BN‐3‐Cyclohexene by Copper‐Assisted Triazole/Gold Catalysis
  作者：Stephen E. Motika、Qiaoyi Wang、Novruz G. Akhmedov、Lukasz Wojtas、Xiaodong Shi

  DOI：10.1002/anie.201604986

  日期：2016.9.12

  as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six‐membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5‐exo vs. 6‐endo) were achieved through catalyst control and sequential dilution. Good functional‐group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates,

  三唑/金（TA-Au）和Cu（OTf）2的组合被认为是促进分子内氢硼化合成六元环胺-硼烷的最佳催化体系。通过催化剂控制和顺序稀释，获得了极高的收率（高达95％）和区域选择性（5-exo vs. 6-endo）。获得了良好的官能团耐受性，因此可以制备高度官能化的环胺-硼烷底物，而这是其他方法无法实现的。氘标记研究支持在金活化炔烃中加入氢化物并随后形成C-B键。
• Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis
  作者：Courtney A. Smith、Stephen E. Motika、Lukasz Wojtas、Xiaodong Shi

  DOI：10.1039/c6cc09794d

  日期：——

  An intermolecular condensation of alkynols and terminal alkynes is reported. Using IPrAuNTf2, an efficient Au-catalyzed cyclization-alkynylation strategy furnishes (2-arylalkynyl) cyclic ethers in moderate to excellent yields (up to 94%). This...

  据报道，炔醇和末端炔烃发生分子间缩合。使用 IPrAuNTf2，一种有效的 Au 催化环化-炔基化策略可以以中等至优异的产率（高达 94%）提供（2-芳基炔基）环醚。这...
• Gold(I)/Chiral Brønsted Acid Catalyzed Enantioselective Hydroamination-Hydroarylation of Alkynes: The Effect of a Remote Hydroxyl Group on the Reactivity and Enantioselectivity
  作者：Valmik S. Shinde、Manoj V. Mane、Kumar Vanka、Arijit Mallick、Nitin T. Patil

  DOI：10.1002/chem.201405061

  日期：2015.1.12

  range of pyrrole‐based aromatic amines to give pyrrole‐embedded aza‐heterocyclic scaffolds bearing a quaternary carbon center. The presence of a hydroxyl group in the alkyne tether turned out to be very crucial for obtaining products in high yields and enantioselectivities. The mechanism of enantioinduction was established by carefully performing experimental and computational studies.

  （R 3 P）AuMe /（S）-3,3'-双（2,4,6-三异丙基苯基）-1,1'-联萘-2,2'催化下炔烃的对映选择性加氢氨化反应报道了磷酸二氢基酯（（S）-TRIP）。炔烃与一系列基于吡咯的芳族胺反应，生成带有季碳中心的吡咯嵌入的氮杂杂环骨架。事实证明，炔烃系链中羟基的存在对于获得高产率和对映选择性的产物非常关键。通过仔细地进行实验和计算研究来建立对映体诱导的机制。