2-benzoxazol-2-yl-1-biphenyl-4-yl-2,2-difluoroethanol | 186828-57-9

• 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: 2-benzoxazol-2-yl-1-biphenyl-4-yl-2,2-difluoroethanol
• 英文别名: 2-(1,3-Benzoxazol-2-yl)-2,2-difluoro-1-(4-phenylphenyl)ethanol
• CAS: 186828-57-9
• 化学式: C₂₁H₁₅F₂NO₂
• 分子量: 351.352
• InChiKey: LGWTVZUAPGUCEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzoxazol-2-yl-1-biphenyl-4-yl-2,2-difluoroethanol 在 二乙胺基三氟化硫 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 2-[2-biphenyl-4-yl-1,1,2,2-tetrafluoroethyl]benzoxazole
  参考文献：
  名称：

  新型二氟亚甲基苯并恶唑和1,2,4-恶二唑衍生物作为有效的非核苷HIV-1逆转录酶抑制剂的合成

  摘要：

  为了制备对HIV具有活性的新的含氟化合物，对一系列苯并恶唑和1,2,4-恶二唑-CF 2 CHOHAr衍生物进行了几种化学修饰。产物（9 - 30），其都具有一个或两个CF 2个基团为抗HIV-1活性进行了测试; 它们没有明显的活性，其中之一具有细胞毒性。

  DOI：

  10.1016/j.jfluchem.2004.12.016
• 作为产物：
  描述：

  对苯基苯甲醛 、 2-(溴二氟甲基)-1,3-苯并噁唑 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以45%的产率得到2-benzoxazol-2-yl-1-biphenyl-4-yl-2,2-difluoroethanol
  参考文献：
  名称：

  2-（溴二氟甲基）苯并恶唑与四（二甲基氨基）乙烯（TDAE）在醛存在下的反应。方便合成2-（二氟甲基）苯并恶唑醇

  摘要：

  发现四（二甲基氨基）乙烯（TDAE）是2-（溴二氟甲基）苯并恶唑1的有效还原剂。所生成的2-（二氟甲基）苯并恶唑阴离子被困与几个醛2 - 9，温和的条件下，得到相应的2-（二氟甲基）苯并唑醇10 - 17，在中度至良好的产率。

  DOI：

  10.1016/s0040-4039(96)02440-9

文献信息

• Reaction of the 2-(bromodifluoromethyl)benzoxazole with tetrakis(dimethylamino)ethylene (TDAE) in the presence of aldehydes. A convenient synthesis of 2-(difluoromethyl)benzoxazole alcohols
  作者：Conrad Burkholder、William R. Dolbier、Maurice Médebielle

  DOI：10.1016/s0040-4039(96)02440-9

  日期：1997.2

  Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluoromethyl) benzoxazole anion was trapped with several aldehydes 2 – 9, under mild conditions, to give the corresponding 2-(difluoromethyl)benzoxazole alcohols 10 – 17, in moderate to good yields.

  发现四（二甲基氨基）乙烯（TDAE）是2-（溴二氟甲基）苯并恶唑1的有效还原剂。所生成的2-（二氟甲基）苯并恶唑阴离子被困与几个醛2 - 9，温和的条件下，得到相应的2-（二氟甲基）苯并唑醇10 - 17，在中度至良好的产率。
• Tetrakis(dimethylamino)ethylene as a Useful Reductant of Some Bromodifluoromethyl Heterocycles. Application to the Synthesis of New <i>gem</i>-Difluorinated Heteroarylated Compounds
  作者：Conrad Burkholder、William R. Dolbier、Maurice Médebielle

  DOI：10.1021/jo980201+

  日期：1998.8.1

  The cyclic voltammetry of the reductive cleavage of some bromodifluoromethyl heterocycles and of the oxidation of the tetrakis(dimethylamino)ethylene was investigated in N,N-dimethylformamide and acetonitrile, at an inert electrode. The systematic investigation of the kinetics of the electrochemical reduction of this series of bromodifluoromethyl compounds provides clear evidence of a concerted electron-transfer-bond-breaking mechanism. Application of the theory of the dissociative electron transfer allowed the estimation of the carbon-halogen bond dissociation energy and the standard potential of the reaction. On the basis of the electrochemical experiments, the tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole (1) and of the 5-(bromodifluoromethyl)-3-phenyl-1,2,4-oxadiazole (4). A stepwise electron transfer with a difluoromethyl radical as intermediate is assumed to take place in this reaction. Under mild conditions, the generated difluoromethyl heterocyclic anion was efficiently trapped with aromatic and heterocyclic aldehydes 7-17 and ketones 18 and 19. In this way, the corresponding beta,beta-difluoro-alpha-heteroarylated alcohols 20-38 were obtained in moderate to good yields and the compounds 20, 21, and 23-27 were tested against the HIV-1 virus.
• Syntheses of new difluoromethylene benzoxazole and 1,2,4-oxadiazole derivatives, as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
  作者：Maurice Medebielle、Samia Ait-Mohand、Conrad Burkhloder、William R. Dolbier、Géraldine Laumond、Anne-Marie Aubertin

  DOI：10.1016/j.jfluchem.2004.12.016

  日期：2005.4

  In an effort to prepare new fluorine-containing compounds, which are active against HIV, several chemical modifications of a series of benzoxazole and 1,2,4-oxadiazole-CF2CHOHAr derivatives were carried out. The products (9–30) which all have one or two CF2 groups were tested for activity against HIV-1; they were devoid of significant activity, one of them being cytotoxic.

  为了制备对HIV具有活性的新的含氟化合物，对一系列苯并恶唑和1,2,4-恶二唑-CF 2 CHOHAr衍生物进行了几种化学修饰。产物（9 - 30），其都具有一个或两个CF 2个基团为抗HIV-1活性进行了测试; 它们没有明显的活性，其中之一具有细胞毒性。