2-(3,5-双(三氟甲基)苯基)乙醇 | 93427-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3,5-双(三氟甲基)苯基)乙醇
• 中文别名: 3,5-三氟甲基苯乙醇
• 英文名称: 2-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol
• 英文别名: 2-(3,5-Bis(trifluoromethyl)phenyl)ethanol；2-[3,5-bis(trifluoromethyl)phenyl]ethanol
• CAS: 93427-28-2
• 化学式: C₁₀H₈F₆O
• mdl: MFCD09839219
• 分子量: 258.163
• InChiKey: ICNQSKXBJAIKCP-UHFFFAOYSA-N

物化性质

• 沸点：
  191.5±35.0 °C(Predicted)
• 密度：
  1.382±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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  2-(3,5-双(三氟甲基)苯基)乙醇 在 咪唑 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 、 苯 为溶剂， 反应 25.0h， 生成 (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(3'-(3,5-bistrifluoromethylphenyl)propyl)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one
  参考文献：
  名称：

  Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates

  摘要：

  On the basis of earlier reported quantitative structure-activity relationship studies, a series of 9beta-16-(arylalkyl)-10-deoxoartemisinins were proposed for synthesis. Several of the new compounds 7 and 10-14 were synthesized, employing the key synthetic intermediate 23. In a second approach, the natural product (+)-artemisinic acid was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogues. Under a new approach, we developed A one step reaction for the interconversion of artemisinin 1 into artemisitene 22 that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of 22 in good yield. The lactone carbonyls, were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF3-etherate/Et3SiH) to afford the desired corresponding pyrans. Six additional halogen-substituted aromatic side chains were installed via 22 furnishing the bioassay candidates 15-20. The analogues were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were additionally tested. in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity, Of these, two were chosen for pharmacokinetic evaluation, 14 and 17.

  DOI：

  10.1021/jm020142z
• 作为产物：
  描述：

  3,5-双三氟甲基苄基溴 在 二异丁基氢化铝 、 magnesium 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(3,5-双(三氟甲基)苯基)乙醇
  参考文献：
  名称：

  开发新型线粒体丙酮酸载体抑制剂来治疗脱发

  摘要：

  在此，我们报告了 UK-5099 新型类似物的体外和体内合成和评估，用于开发治疗脱发的线粒体丙酮酸载体 (MPC) 抑制剂。通过改变命中化合物的四个位置，即N1位上的烷基、吲哚核心上的取代基、各种芳香族和杂芳香族核心结构以及各种迈克尔受体，获得了对构效关系的全面了解。主要发现是，N1 位带有 3,5-双（三氟甲基）苄基的抑制剂在增加细胞乳酸产量方面比JXL001 (UK-5099) 具有更好的活性。此外，具有7-氮杂吲哚杂环的类似物JXL069也被证明具有显着的MPC抑制活性，这进一步增加了药物设计的化学空间。最后，超过10种类似物在剃毛小鼠身上进行了局部治疗试验，并促进了小鼠明显的毛发生长。

  DOI：

  10.1021/acs.jmedchem.0c01570

文献信息

• Formal hydration of non-activated terminal olefins using tandem catalysts
  作者：Yongsheng Yang、Jiayi Guo、Huimin Ng、Zhiyong Chen、Peili Teo

  DOI：10.1039/c3cc48810a

  日期：——

  The hydration of terminal olefins to secondary alcohols has been achieved using a Pd(II)/Ru(II) catalyst combination with high regioselectivity and yields. Both vinyl arenes and aliphatic olefins can be hydrated easily with the tandem catalyst system using a low catalyst loading of 1 mol%.

  使用Pd(II)/Ru(II)催化剂组合，成功实现了端烯向仲醇的高区域选择性和产率的水合反应。不论是乙烯基芳烃还是脂肪族烯烃，都能在低催化剂负载量（1 mol%）下，利用这种串联催化体系轻松进行水合反应。
• [EN] NOVEL PIPERIDINE COMPOUND<br/>[FR] NOUVEAU COMPOSE DE PIPERIDINE
  申请人：TANABE SEIYAKU CO

  公开号：WO2003099787A1

  公开（公告）日：2003-12-04

  The present invention provides a novel piperidine compound of the formula [I]: wherein Ring A represents an optionally substituted benzene ring, Ring B represents an optionally substituted benzene ring, R1 represents an optionally substituted alkyl group, an optionally substituted hydroxyl group, etc., or a group of the formula: (a) wherein R11 and R12 are the same or different, and each represents hydrogen atom, a substituted carbonyl group, a substituted sulfonyl group, an optionally substituted alkyl group, etc., R2 represents hydrogen atom, etc., Z represents oxygen atom or a group represented by -N(R3)-, R3 represents hydrogen atom or an alkyl group, etc., R4 represents hydrogen atom or an alkyl group, etc.,or a pharmaceutically acceptable salt thereof.

  本发明提供了一种新型哌啶化合物，其化学式为[I]：其中环A代表可选择取代的苯环，环B代表可选择取代的苯环，R1代表可选择取代的烷基团，可选择取代的羟基团等，或者化学式的一个基团：(a)其中R11和R12相同或不同，每个代表氢原子，取代的羰基团，取代的磺酰基团，可选择取代的烷基团等，R2代表氢原子等，Z代表氧原子或由-N(R3)-表示的基团，R3代表氢原子或烷基团等，R4代表氢原子或烷基团等，或其药学上可接受的盐。
• [EN] 1,2,4-SUBSTITUERTE 1,2,3,4-TETRAHYDRO-AND 1,2 DIHYDRO-QUINOLINE AND 1,2,3,4-TETRAHYDRO-QUINOXALINE DERIVATIVES AS CETP INHIBITORS FOR THE TREATMENT OF ATHEROSCLEROSIS AND OBESITY<br/>[FR] DERIVES DE 1,2,3,4-TETRAHYDRO- ET 1,2 DIHYDRO-QUINOLEINE ET 1,2,3,4-TETRAHYDRO-QUINOXALINE 1,2,4-SUBSTITUES, UTILES COMME INHIBITEURS DE CETP POUR LE TRAITEMENT DE L'ATHEROSCLEROSE ET DE L'OBESITE
  申请人：PFIZER PROD INC

  公开号：WO2004085401A1

  公开（公告）日：2004-10-07

  Quinoline and quinoxaline compounds of formula I and III wherein the subtituent are as defined in claims 1 and 15, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases in some mammals, including humans.

  喹啉和喹啉并喹啉化合物的公式I和III，其中取代基如权利要求1和15中所定义的，含有这种化合物的药物组合物以及使用这种化合物来提高某些血浆脂质水平，包括高密度脂蛋白胆固醇，并降低其他一些血浆脂质水平，如LDL胆固醇和甘油三酯，并因此治疗由HDL胆固醇水平低和/或LDL胆固醇和甘油三酯水平高加重的疾病，如动脉粥样硬化和心血管疾病在某些哺乳动物中，包括人类。
• Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis
  作者：Guangbin Dong、Peili Teo、Zachary K. Wickens、Robert H. Grubbs

  DOI：10.1126/science.1208685

  日期：2011.9.16

  create alcohols by guiding water to attack carbon-carbon bonds in the opposite sense than it normally would. Alcohol synthesis is critical to the chemical and pharmaceutical industries. The addition of water across olefins to form primary alcohols (anti-Markovnikov olefin hydration) would be a broadly useful reaction but has largely proven elusive; an indirect hydroboration/oxidation sequence requiring

  三种催化剂通过引导水以与通常相反的方式攻击碳 - 碳键来产生醇。酒精合成对化学和制药行业至关重要。通过烯烃加入水以形成伯醇（反马尔科夫尼科夫烯烃水合）将是一个广泛有用的反应，但在很大程度上已证明难以捉摸；需要化学计量硼烷和氧化剂的间接硼氢化/氧化顺序是目前最实用的方法。在这里，我们报告了一种使用三重中继催化系统的更直接的方法，该系统将钯催化氧化、酸催化水解和钌催化还原循环结合起来。芳基取代的末端烯烃通过与水的净反应以良好的收率和出色的区域选择性转化为伯醇。
• Enantioselective radical C–H amination for the synthesis of β-amino alcohols
  作者：Kohki M. Nakafuku、Zuxiao Zhang、Ethan A. Wappes、Leah M. Stateman、Andrew D. Chen、David A. Nagib

  DOI：10.1038/s41557-020-0482-8

  日期：2020.8

  but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C–H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective

  不对称的基本C–H功能化是解决现代综合挑战的罕见但功能强大的工具。特别是，醇的对映体和区域选择性C–H胺化以获取具有医学价值的手性β-氨基醇仍然难以实现。为了解决这一挑战，设计了一种自由基中继分子伴侣策略，其中将一种醇瞬态转化为经过分子内H原子转移（HAT）的亚氨酸酯自由基。通过利用能量转移催化来介导选择性自由基的产生和被手性铜催化剂的拦截，该区域选择性HAT也被赋予了对映选择性。这种多催化，不对称自由基C–H胺的成功开发，使人们能够广泛地从多种含有烷基，烯丙基，苄基和炔丙基C–H键的醇中获得手性β-氨基醇。