1,1,1,3,3,3-六氟-2-(4-(甲基氨基)苯基)-2-丙醇 | 1481-11-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,1,1,3,3,3-六氟-2-(4-(甲基氨基)苯基)-2-丙醇
• 英文名称: 1,1,1,3,3,3-hexafluoro-2-(4-(methylamino)phenyl)propan-2-ol
• 英文别名: N-methyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]aniline；1,1,1,3,3,3-hexafluoro-2-[4-(methylamino)phenyl]propan-2-ol
• CAS: 1481-11-4
• 化学式: C₁₀H₉F₆NO
• 分子量: 273.178
• InChiKey: COUCSXYYYRCQOG-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  135-140 °C(Press: 20 Torr)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-六氟-2-(4-(甲基氨基)苯基)-2-丙醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-(3-bromo-4-(methylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Transrepression-Selective Liver X Receptor (LXR) Ligands with 5,11-Dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one Skeleton

  摘要：

  To obtain novel transrepression-selective liver X receptor (LXR) ligands, we adopted a strategy of reducing the transactivational agonistic activity of the 5,11-dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one derivative 10, which exhibits LXR-mediated transrepressional and transactivational activity. Structural modification of 10 based on the reported X-ray crystal structure of the LXR ligand-binding domain led to a series of compounds, of which almost all exhibited transrepressional activity at 1 or 10 mu M but showed no transactivational activity even at 30 mu M. Among the compounds obtained, 18 and 22 were confirmed to have LXR-dependent transrepressional activity by using peritoneal macrophages from wild-type and LXR-null mice. A newly developed fluorescence polarization assay indicated that they bind directly to LXR alpha. Next, further structural modification was performed with the guidance of docking simulations with LXR alpha, focusing on enhancing the binding of the ligands with LXR alpha through the introduction of substituents or heteroatom(s). Among the compounds synthesized, compound 48, bearing a hydroxyl group, showed potent, selective, and dose-dependent transrepressional activity.

  DOI：

  10.1021/jm3002394
• 作为产物：
  描述：

  N-烯丙基-n-甲基苯胺 以 苯 为溶剂， 反应 45.0h， 生成 1,1,1,3,3,3-六氟-2-(4-(甲基氨基)苯基)-2-丙醇
  参考文献：
  名称：

  Kobayashi, Yoshiro; Nagai, Takabumi; Kumadaki, Itsumaro, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 12, p. 5031 - 5035

  摘要：

  DOI：

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。
• [EN] ANILINO LIVER X-RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RECEPTEURS X DU FOIE A STRUCTURE ANILINO
  申请人：PHARMACIA CORP

  公开号：WO2003099769A1

  公开（公告）日：2003-12-04

  The present invention is directed to selective LXR modulators, small molecule compounds corresponding to Formula I and is further directed to a process of treating a condition in a mammal that is modulated by LXR using a therapeutically effective dose of a compound of Formula I.

  本发明涉及选择性LXR调节剂，对应于式I的小分子化合物，并进一步涉及利用式I化合物的治疗有效剂量来治疗受LXR调节的哺乳动物病症的方法。
• Anti-hypertensive polyhaloisopropyl-substituted arylureas
  申请人：Schering Corporation

  公开号：US04093742A1

  公开（公告）日：1978-06-06

  Novel polyhaloisopropyl-substituted arylureas having potent antihypertensive properties are disclosed herein.

  这里披露了具有强效降压作用的新型多卤异丙基取代芳基脲类化合物。
• 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。
• Para-polyfluoroisopropyl-anilino-2-oxazoline compounds, pharmaceutical
  申请人：Schering Corporation

  公开号：US04081547A1

  公开（公告）日：1978-03-28

  Novel para-polyfluoroisopropyl-anilino-2-oxazolines and thiazolines are provided which exhibit potent antihypertensive properties without significant CNS depression.

  提供了新型对氟异丙基苯胺基-2-噁唑烯和噻唑烯，具有强效的降压作用，且不会引起明显的中枢神经系统抑制。