3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine | 125680-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine
• 英文别名: 3-(4-hydroxy-3-nitrophenyl)-3-trifluoromethyl-3H-diazirine；2-Nitro-4-[3-(trifluoromethyl)diazirin-3-yl]phenol
• CAS: 125680-82-2
• 化学式: C₈H₄F₃N₃O₃
• 分子量: 247.133
• InChiKey: QRDOTNRCFQQHGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 52.0h， 生成 <2-nitro-4-(2,2,2-trifluoro-1-methoxyethyl)phenoxy>acetic acid methyl ester
  参考文献：
  名称：

  Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.

  摘要：

  合成了具有硝基和醚基取代基的3-苯基-3-三氟甲基-二氟啉衍生物，作为光标记产物的卡宾前驱体用于色谱检测。在甲醇或环己烷中光解二氟啉分别生成了分子间的O-H或C-H插入产物。光产物的光谱特性使得在大多数生物大分子的吸收可以忽略的光谱区域内进行光标记产物的检测成为可能。还制备了二氟啉的碳-14同位素类似物，用于微量标记产物的检测。这些硝基取代的芳基二氟啉应适用于广泛的光亲和标记研究，从示踪实验到通过HPLC配合光谱光度检测进行标记产物的制备分离。

  DOI：

  10.1248/cpb.42.826
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine 在 硝酸 、 三溴化硼 作用下， 以 二氯甲烷 、 乙酸酐 为溶剂， 反应 0.5h， 生成 3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine
  参考文献：
  名称：

  A photoreactive probe that differentiates the binding sites of noncompetitive GABA receptor antagonists

  摘要：

  gamma-Aminobutyric acid (GABA) receptors are postsynaptic membrane protein complexes that are important not only in the regulation of the nervous system but also as targets of drugs and insecticides. We synthesized a photoreactive straight-chain noncompetitive antagonist (NCA), 2-nitro-4-[3-(trifluoromethyl)3H- diazirin-3-yl]phenyl 4-(4-methoxycarbonyl-1-butynyl)benzoate (NMB), to probe the NCA binding site. Our data show that this probe labels the NCA site and demonstrate that the NCA insecticide fipronil binds at a site distinct from that of other NCAs, such as picrotoxinin and 4'-ethynyl-4-n-propyl-bicycloorthobenzoate. The unique molecule NMB will be useful in identifying the cross-linking site of straight-chain NCAs in GABA receptors and mapping allosteric binding sites. Such studies should provide invaluable information in designing novel NCAs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.118

文献信息

• Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.
  作者：Yasumaru HATANAKA、Makoto HASHIMOTO、Hitoshi NAKAYAMA、Yuichi KANAOKA

  DOI：10.1248/cpb.42.826

  日期：——

  3-Phenyl-3-trifluoromethyl-diazirine derivatives with nitro and alkoxy substituents on their aromatic ring have been synthesized as carbene precursors for chromogenic detection of photolabeled products. Photolysis of the diazirines in methanol or cyclohexane gave intermolecular O-H or C-H insertion products, respectively. Spectroscopic properties of the photoproducts are such that detection of photolabeled products may be performed in a spectral region where the absorption due to most biological macromolecules is negligible. A carbon-14 analog of the diazirine was also prepared for microscale detection of labeled products. These nitro-substituted aryl diazirines should be applicable to a wide range of photoaffinity labeling studies, from tracer experiments to preparative isolation of labeled products by HPLC with spectrophotometric detection.

  合成了具有硝基和醚基取代基的3-苯基-3-三氟甲基-二氟啉衍生物，作为光标记产物的卡宾前驱体用于色谱检测。在甲醇或环己烷中光解二氟啉分别生成了分子间的O-H或C-H插入产物。光产物的光谱特性使得在大多数生物大分子的吸收可以忽略的光谱区域内进行光标记产物的检测成为可能。还制备了二氟啉的碳-14同位素类似物，用于微量标记产物的检测。这些硝基取代的芳基二氟啉应适用于广泛的光亲和标记研究，从示踪实验到通过HPLC配合光谱光度检测进行标记产物的制备分离。
• A photoreactive probe that differentiates the binding sites of noncompetitive GABA receptor antagonists
  作者：Hiroshi Shimotahira、Sayaka Fusazaki、Izumi Ikeda、Yoshihisa Ozoe

  DOI：10.1016/j.bmcl.2011.01.118

  日期：2011.3

  gamma-Aminobutyric acid (GABA) receptors are postsynaptic membrane protein complexes that are important not only in the regulation of the nervous system but also as targets of drugs and insecticides. We synthesized a photoreactive straight-chain noncompetitive antagonist (NCA), 2-nitro-4-[3-(trifluoromethyl)3H- diazirin-3-yl]phenyl 4-(4-methoxycarbonyl-1-butynyl)benzoate (NMB), to probe the NCA binding site. Our data show that this probe labels the NCA site and demonstrate that the NCA insecticide fipronil binds at a site distinct from that of other NCAs, such as picrotoxinin and 4'-ethynyl-4-n-propyl-bicycloorthobenzoate. The unique molecule NMB will be useful in identifying the cross-linking site of straight-chain NCAs in GABA receptors and mapping allosteric binding sites. Such studies should provide invaluable information in designing novel NCAs. (C) 2011 Elsevier Ltd. All rights reserved.