2-氨基-2-(4-(三氟甲基)苯基)乙醇 | 473416-36-3

• 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-氨基-2-(4-(三氟甲基)苯基)乙醇
• 中文别名: 2-氨基-2-(4-三氟甲基苯基)乙醇
• 英文名称: 2-amino-2-(4-(trifluoromethyl)phenyl)ethanol
• 英文别名: 2-amino-2-(4-(trifluoromethyl)phenyl)ethan-1-ol；(±)-2-amino-2-[4-(trifluoromethyl)phenyl]ethanol；2-amino-2-[4-(trifluoromethyl)phenyl]ethanol
• CAS: 473416-36-3
• 化学式: C₉H₁₀F₃NO
• mdl: MFCD11213652
• 分子量: 205.18
• InChiKey: VDJAPRZLEXCFHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2-氨基-2-(4-(三氟甲基)苯基)乙醇 在 碘甲烷 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 26.0h， 生成 tert-butyl (2-(4-(((4-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazol-2-yl)amino)methyl)benzamido)phenyl)carbamate
  参考文献：
  名称：

  Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a N-(2-Aminophenyl)-benzamide Binding Unit

  摘要：

  A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100 000 nM; HDAC8: IC50 = 25 000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.

  DOI：

  10.1021/acs.jmedchem.5b00545
• 作为产物：
  描述：

  4-(三氟甲基)-DL-苯甘氨酸 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以46%的产率得到2-氨基-2-(4-(三氟甲基)苯基)乙醇
  参考文献：
  名称：

  Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a N-(2-Aminophenyl)-benzamide Binding Unit

  摘要：

  A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100 000 nM; HDAC8: IC50 = 25 000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.

  DOI：

  10.1021/acs.jmedchem.5b00545

文献信息

• Directed β C–H Amination of Alcohols via Radical Relay Chaperones
  作者：Ethan A. Wappes、Kohki M. Nakafuku、David A. Nagib

  DOI：10.1021/jacs.7b05214

  日期：2017.8.2

  for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom

  已经开发了一种自由基介导的醇类 β CH 胺化策略。该方法采用自由基中继伴侣，作为无痕导向剂，通过 1,5-氢原子转移 (HAT) 促进选择性 CH 官能化，并使氨在醇的 β 碳上净结合。本文介绍的分子伴侣能够直接访问亚胺酸酯自由基，从而使其首次用于 H 原子提取。简化的方案能够将醇快速转化为它们的 β-氨基类似物（通过将醇原位转化为亚胺酸酯、定向 CH 胺化和水解为 NH2）。机械实验表明 HAT 是限速的，而分子内胺化是产物和立体决定。
• Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
  作者：Xinyun Liu、Johnny H Phan、Benjamin J Haugeberg、Shrikant S Londhe、Michael D Clift

  DOI：10.3762/bjoc.13.282

  日期：——

  A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative

  报道了一种通过醌催化的1,2-氨基醇氧化甲酰化合成亚胺的新方法。各种容易获得的氨基醇和伯胺都可以反应生成N保护的亚胺产品。提出的方法为亚胺合成提供了一种新颖的有机催化方法，并证明了醌催化的氧化CC键裂解的合成多功能性。
• 2-Cyanophenyl fused heterocyclic compounds, and compositions and uses thereof
  申请人：Wei Zhi-Liang

  公开号：US20080275037A1

  公开（公告）日：2008-11-06

  Fused heterocyclic compounds are provided according to formula 1: where R 1 , R 2 , R 3 , and m are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others.

  根据公式1提供了融合的杂环化合物：其中R1、R2、R3和m的定义如本文所述。提供的化合物及其药物组合物对于预防和治疗包括人类在内的哺乳动物的多种疾病状况是有用的，包括但不限于疼痛、炎症、认知障碍、焦虑、抑郁等。
• [EN] PYRIMIDONE CARBOXAMIDE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS PYRIMIDONE CARBOXAMIDE UTILISÉS EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2015096651A1

  公开（公告）日：2015-07-02

  Disclosed are pyrimidine carboxamide compounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2), pharmaceutical compositions and uses thereof.

  揭示了式（I）的嘧啶羧酰胺化合物，这些化合物可用作治疗与磷酸二酯酶2（PDE2）相关的中枢神经系统疾病的治疗剂，以及其药物组合物和用途。
• Catalytic β C–H amination <i>via</i> an imidate radical relay
  作者：Leah M. Stateman、Ethan A. Wappes、Kohki M. Nakafuku、Kara M. Edwards、David A. Nagib

  DOI：10.1039/c8sc05685d

  日期：——

  An iodine-catalyzed strategy for β C–H amination of alcohols is enabled by a chemo-, regio-, and stereo-selective H-atom transfer mechanism.

  一种碘催化的策略，用于醇的β C-H氨基化，通过化学、位置和立体选择性的氢原子转移机制实现。