1,1,1-三氟-2-羟基-2-(2-氨基苯基)乙烷 | 205756-49-6

• 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: 1,1,1-三氟-2-羟基-2-(2-氨基苯基)乙烷
• 英文名称: 1-(2-aminophenyl)-2,2,2-trifluoroethanol
• 英文别名: 1-(2-aminophenyl)-2,2,2-trifluoroethan- 1-ol；1,1,1-trifluoro-2-hydroxy-2-(2-aminophenyl)ethane
• CAS: 205756-49-6
• 化学式: C₈H₈F₃NO
• mdl: MFCD20691011
• 分子量: 191.153
• InChiKey: MEYKEXQUMCFNCS-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-2-羟基-2-(2-氨基苯基)乙烷 在 1,10-菲罗啉 、 1,2-肼二羧酸二乙酯 、 氧气 、 potassium carbonate 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到1-(2-氨基苯基)-2,2,2-三氟乙烷酮
  参考文献：
  名称：

  Selective Colorimetric Sensing of Anions in Aqueous Media through Reversible Covalent Bonding

  摘要：

  Selective colorimetric sensing of anions in aqueous media has been studied, which involves reversible covalent bonding as key binding interactions. By introducing a simple nitro chromophore into an o-(carboxamido)trifluoroacetophenone ionophore that recognizes anions through reversible covalent bonding, we have realized a complete selectivity in colorimetric sensing of cyanide among competing anions such as fluoride. acetate, and dihydrogen phosphate in aqueous media. Such selectivity is explained by dominant reversible covalent bonding over hydrogen bonding, which leads to indirect internal charge transfer. The sensing system is readily converted into a polymeric analogue, demonstrating its potential applicability to develop a naked eye detection material for highly toxic cyanide ions.

  DOI：

  10.1021/jo900573v
• 作为产物：
  描述：

  1-(2-氨基-5-氯苯基)-2,2,2-三氟乙酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到1,1,1-三氟-2-羟基-2-(2-氨基苯基)乙烷
  参考文献：
  名称：

  Synthesis and evaluation of analogs of Efavirenz (SUSTIVATM) as HIV-1 reverse transcriptase inhibitors

  摘要：

  Efavirenz (SUSTIVA(TM)) is a potent non-nucleoside reverse transcriptase inhibitor. Due to the observation of breakthrough mutations of the reverse transcriptase enzyme during Efavirenz therapy, we sought to develop an optimized second generation series. To that end, SAR of the substituents on the aromatic ring was undertaken and the results are summarized here. The 5,6-difluoro (4f) and the 6-methoxy (4m) substituted benzoxazinones were determined to be equipotent, and as a result such substitution patterns will be incorporated in second generation scaffolds. (C) 1999 DuPont Pharmaceuticals. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00486-2

文献信息

• Superbase-Mediated Indirect Friedländer Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
  作者：Rahul P.、Nitha P. R.、Vishnu K. Omanakuttan、Sheba Ann Babu、P. Sasikumar、Vakayil K. Praveen、Henning Hopf、Jubi John

  DOI：10.1002/ejoc.202000365

  日期：2020.5.29

  A transition metal‐free superbase mediated indirect Friedländer reaction was developed for accessing functionalized quinolines using o‐aminobenzyl alcohol and ketones with an active methylene moiety. The reaction was employed in the functionalization of natural products and the applicability of the reaction for gram‐scale synthesis of quinolines was also demonstrated.

  开发了一种不含过渡金属的超碱介导的间接Friedländer反应，可使用邻氨基苯甲醇和具有活性亚甲基的酮来获得官能化的喹啉。该反应被用于天然产物的功能化，并且也证明了该反应在克规模合成喹啉中的适用性。
• [EN] INHIBITORS OF ADENYLATE-FORMING ENZYME MENE<br/>[FR] INHIBITEURS DE L'ENZYME MENE FORMANT L'ADÉNYLATE CYCLASE
  申请人：MEMORIAL SLOAN KETTERING CANCER CENTER

  公开号：WO2020163673A1

  公开（公告）日：2020-08-13

  Provided herein are compounds of Formula (I) and pharmaceutically acceptable salts or tautomers thereof which may inhibit adenylate-forming enzymes. Also provided are pharmaceutical compositions, kits, uses, and methods involving the inventive compounds for the treatment and/or prevention of an infectious disease (e.g., bacterial infection (e.g., tuberculosis, methicillin- resistant Staphylococcus aureus)).

  本文提供了式（I）的化合物及其药用可接受的盐或互变异构体，这些化合物可能抑制腺苷酸形成酶。还提供了涉及这些创新化合物用于治疗和/或预防传染病（例如细菌感染（例如结核病、耐甲氧西林金黄色葡萄球菌））的药物组合物、试剂盒、用途和方法。
• Chiral discrimination of α-amino acids with a C₂-symmetric homoditopic receptor
  作者：Sunderraman Sambasivan、Dae-sik Kim、Kyo Han Ahn

  DOI：10.1039/b919957h

  日期：——

  Chiral discrimination of α-amino acids has been realized by a C2-symmetric homoditopic receptor, which is based on a binaphthyl chiral skeleton with 2,2′diisopropoxy substituents and a common binding side arm, (o-carboxamido)-trifluoroacetophenone moiety, in the 3,3′-positions, which recognizes α-amino acids as their amino carboxylate forms through formation of stabilized adducts.

  通过一种C2对称的同位受体实现了对α-氨基酸的手性分辨，该受体基于具有2,2'-二异丙氧基取代基和共通结合侧臂（o-氨基酰基）-三氟乙酰苯酮部分的双萘手性骨架，在3,3'-位置，能够以其氨基羧酸盐形式识别α-氨基酸，通过形成稳定的加合物。
• Electrophilic ketones for the treatment of herpesvirus infections
  申请人：G. D. Searle & Co., Corporate Patent Department

  公开号：US20030119721A1

  公开（公告）日：2003-06-26

  A class of compounds is described which can be used for the treatment of viral infections. Compounds of particular interest are defined by Formula II 1 wherein each of R 1 , R 2 , and R 3 is independently selected from hydrido, halo, and nitro; wherein R 8 is selected from haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, optionally substituted arylalkoxy and optionally substituted aryloxyalkyl; wherein Y is selected from fluoroalkyl, and 2 wherein R 9 is alkylamino; or a pharmaceutically-acceptable salt or tautomer thereof.

  描述了一类化合物，可用于治疗病毒感染。 特别感兴趣的化合物由Formula II1定义，其中R1、R2和R3中的每一个独立地选择自氢代基、卤素和硝基；其中R8选择自卤代烷基、可选地取代的芳基、可选地取代的芳基烷基、可选地取代的杂环芳基、可选地取代的芳基烷氧基和可选地取代的芳氧基烷基；其中Y选择自氟代烷基，以及其中R9是烷基氨基；或其药用可接受的盐或互变异构体。
• Fluorescence modulation in anion sensing by introducing intramolecular H-bonding interactions in host–guest adducts
  作者：Yun Mi Chung、Balamurali Raman、Dae-Sik Kim、Kyo Han Ahn

  DOI：10.1039/b510795d

  日期：——

  Fluorescence signaling in anion binding is modulated from quenching to enhancement by intramolecular H-bonding stabilization of anion–ionophore adducts; the intramolecular H-bonding is suggested to suppress the quenching processes otherwise possible and increase the conformational rigidity of the anionic adducts, leading to fluorescence enhancement in a selective fashion towards cyanide ion, among the various anions examined.

  阴离子结合中的荧光信号通过分子内氢键稳定阴离子-离子载体加合物，从淬灭调节为增强；分子内氢键被认为抑制了可能发生的淬灭过程，并增加了阴离子加合物的构象刚性，从而在各类阴离子中选择性地增强了对氰离子的荧光增强效果。