2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol | 71280-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
• 英文别名: 2-(3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol；3,4-dihydro-7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H-1,4-benzoxazine；2-(3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol；2-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol；2-(3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
• CAS: 71280-80-3
• 化学式: C₁₁H₉F₆NO₂
• 分子量: 301.188
• InChiKey: ATVQBUVVLUXSHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol 、 苯磺酰氯 在 2,6-二甲基吡啶 作用下， 以 丙酮 为溶剂， 生成 2-(4-Benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol
  参考文献：
  名称：

  Discovery and optimization of a novel series of liver X receptor-α agonists

  摘要：

  A novel series of hexafluorocarbinols were discovered as potent activators of the liver X receptor-alpha using a fluorescence polarization assay. Structure-activity relationship study led to the identification of compounds that are more potent agonists than the endogenous ligand, 24(S), 25-epoxycholesterol, with similar efficacy. Several compounds, including T0901317, were shown to have desirable pharmacokinetic profiles suitable for in vivo studies. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.015
• 作为产物：
  描述：

  7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H-1,4-benzoxazin-3(4H)-one 在 盐酸 、 二硼烷(4) 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
  参考文献：
  名称：

  Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic

  摘要：

  聚氟羟基异丙基双环和三环碳基苯酰胺，例如2,3-二氢-7-甲基-9-[2,2,2-三氟-1-羟基-1-(三氟甲基)乙基]-5H-吡啶[1,2,3-de]-1,4-苯并噁唑-5-酮，可用作降压药物。

  公开号：

  US04251534A1

文献信息

• Cobalt-Catalyzed Selective Functionalization of Aniline Derivatives with Hexafluoroisopropanol
  作者：He Zhao、Shuo Zhao、Xiu Li、Yinyue Deng、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acs.orglett.8b03666

  日期：2019.1.4

  A cobalt-catalyzed site-selective functionalization of aniline derivatives with hexafluoroisopropanol, which enables the synthesis of a wide array of fluoroalkylated anilines, a class of highly valuable building blocks for further preparation of fluorinated functional products, is reported. The developed transformation proceeds with operational simplicity, use of earth-abundant metal catalyst, broad

  报道了用六氟异丙醇对苯胺衍生物进行钴催化的位点选择性官能化，这使得能够合成各种各样的氟代烷基化苯胺，这是一类非常有价值的用于进一步制备氟化功能产物的结构单元。所开发的转化过程将以操作简便，使用富含地球的金属催化剂，广泛的底物范围，良好的官能团耐受性和温和的反应条件进行。
• LXR modulators
  申请人：Chao J. Hannguang

  公开号：US20070093470A1

  公开（公告）日：2007-04-26

  A compound of formula I wherein A, X, q, R 1 , R 2a , R 2b , R 2c , R 3a , and R 3b are defined herein.

  其中A、X、q、R1、R2a、R2b、R2c、R3a和R3b在此处定义。
• Copper(II)‐Catalysed Aerobic Oxidative Coupling of Arylamines with Hexafluoroisopropanol: An Alternative Methodology for Constructing Fluorinated Compounds
  作者：Liangying Wu、Yang Song、Zhanchong Li、Jiabao Guo、Xiaoquan Yao

  DOI：10.1002/adsc.202001048

  日期：2021.1.5

  The selective functionalisation of arylamine derivatives with hexafluoroisopropanol through copper(II)‐catalysed aerobic oxidative coupling was developed to generate various fluoroalkylated arylamines under mild conditions. This method has a wide substrate scope with excellent functional group tolerance and provides the fluorinated products in good to excellent yields. Furthermore, preliminary studies

  开发了在铜（II）催化的需氧氧化偶联作用下，六氟异丙醇对芳胺衍生物的选择性官能化反应，可在温和条件下生成各种氟代烷基化芳基胺。该方法具有广泛的底物范围，具有优异的官能团耐受性，并且以良好至优异的产率提供了氟化产物。此外，初步研究表明该反应是通过自由基机理发生的。该协议使用大气中的O 2作为氧化剂，为构建氟化化合物提供了另一种绿色途径。
• Identification of bicyclic hexafluoroisopropyl alcohol sulfonamides as retinoic acid receptor-related orphan receptor gamma (RORγ/RORc) inverse agonists. Employing structure-based drug design to improve pregnane X receptor (PXR) selectivity
  作者：Hua Gong、David S. Weinstein、Zhonghui Lu、James J.-W. Duan、Sylwia Stachura、Lauren Haque、Ananta Karmakar、Hemalatha Hemagiri、Dhanya Kumar Raut、Arun Kumar Gupta、Javed Khan、Dan Camac、John S. Sack、Andrew Pudzianowski、Dauh-Rurng Wu、Melissa Yarde、Ding-Ren Shen、Virna Borowski、Jenny H. Xie、Huadong Sun、Celia D'Arienzo、Marta Dabros、Michael A. Galella、Faye Wang、Carolyn A. Weigelt、Qihong Zhao、William Foster、John E. Somerville、Luisa M. Salter-Cid、Joel C. Barrish、Percy H. Carter、T.G. Murali Dhar

  DOI：10.1016/j.bmcl.2017.12.006

  日期：2018.1

  We disclose the optimization of a high throughput screening hit to yield benzothiazine and tetrahydroquinoline sulfonamides as potent ROR gamma t inverse agonists. However, a majority of these compounds showed potent activity against pregnane X receptor (PXR) and modest activity against liver X receptor alpha (LXR alpha). Structure-based drug design (SBDD) led to the identification of benzothiazine and tetrahydro-quinoline sulfonamide analogs which completely dialed out LXR alpha activity and were less potent at PXR. Pharmacodynamic (PD) data for compound 35 in an IL-23 induced IL-17 mouse model is discussed along with the implications of a high Y-max in the PXR assay for long term preclinical pharmacokinetic (PK) studies. (C) 2017 Elsevier Ltd. All rights reserved.
• US4251534A
  申请人：——

  公开号：US4251534A

  公开（公告）日：1981-02-17