5-Nitro-2-(4-trifluoromethylphenyl)benzyl alcohol | 243122-83-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Nitro-2-(4-trifluoromethylphenyl)benzyl alcohol
• 英文别名: [5-Nitro-2-[4-(trifluoromethyl)phenyl]phenyl]methanol
• CAS: 243122-83-0
• 化学式: C₁₄H₁₀F₃NO₃
• 分子量: 297.234
• InChiKey: HCIMUMBSBGKHOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Nitro-2-(4-trifluoromethylphenyl)benzyl alcohol 在 platinum(IV) oxide PPA 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-2-tert-Butoxycarbonylamino-N-(7-trifluoromethyl-9H-fluoren-2-yl)-succinamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and biological activities of aryl-ether-, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT-2

  摘要：

  Excitatory amino acid transporters (EAATs) play a pivotal role in maintaining glutamate homeostasis in the mammalian central nervous system, with the EAAT-2 subtype thought to be responsible for the bulk of the glutamate uptake in forebrain regions. A complete elucidation of the functional role of EAAT-2 has been hampered by the lack of potent and selective pharmacological tools. In this study, we describe the synthesis and biological activities of novel aryl-ether, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of EAAT-2. Compound (16) represents one of the most potent (IC50 = 85 +/- 5 nM) and selective inhibitors of EAAT-2 identified to date. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.003
• 作为产物：
  描述：

  2-溴-5-硝基苯甲酸 在 锂硼氢 、 硫酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 36.0h， 生成 5-Nitro-2-(4-trifluoromethylphenyl)benzyl alcohol
  参考文献：
  名称：

  Regiospecific Synthesis of Substituted Nitrofluorenes and Aminofluorenes with the Negishi Coupling Reaction as Key Step

  摘要：

  DOI：

  10.1055/s-1999-3537

文献信息

• Synthesis and biological activities of aryl-ether-, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT-2
  作者：Alexander Greenfield、Cristina Grosanu、John Dunlop、Beal McIlvain、Tikva Carrick、Brian Jow、Qiang Lu、Dianne Kowal、John Williams、John Butera

  DOI：10.1016/j.bmcl.2005.08.003

  日期：2005.11

  Excitatory amino acid transporters (EAATs) play a pivotal role in maintaining glutamate homeostasis in the mammalian central nervous system, with the EAAT-2 subtype thought to be responsible for the bulk of the glutamate uptake in forebrain regions. A complete elucidation of the functional role of EAAT-2 has been hampered by the lack of potent and selective pharmacological tools. In this study, we describe the synthesis and biological activities of novel aryl-ether, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of EAAT-2. Compound (16) represents one of the most potent (IC50 = 85 +/- 5 nM) and selective inhibitors of EAAT-2 identified to date. (c) 2005 Elsevier Ltd. All rights reserved.
• Regiospecific Synthesis of Substituted Nitrofluorenes and Aminofluorenes with the Negishi Coupling Reaction as Key Step
  作者：Markus Klein

  DOI：10.1055/s-1999-3537

  日期：1999.7