2-(bromodifluoromethyl)-4-methylbenzoxazole | 1345459-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(bromodifluoromethyl)-4-methylbenzoxazole
• 英文别名: 2-[Bromo(difluoro)methyl]-4-methyl-1,3-benzoxazole
• CAS: 1345459-54-2
• 化学式: C₉H₆BrF₂NO
• 分子量: 262.054
• InChiKey: KEJLFRYOWFHLIB-UHFFFAOYSA-N

物化性质

• 沸点：
  224.5±40.0 °C(Predicted)
• 密度：
  1.668±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(bromodifluoromethyl)-4-methylbenzoxazole 、 2-丙-1-烯-2-基苯甲酸 在 copper(I) oxide 、 potassium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以93%的产率得到3-[2,2-difluoro-2-(4-methylbenzo[d]oxazol-2-yl)ethyl]-3-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  铜（I）催化烯烃的氧二氟烷基化：内酯功能化的途径

  摘要：

  在温和的反应条件下，开发了一种有效的铜（I）催化的不饱和羧酸的氧二氟烷基化反应。各种α-溴二氟甲基取代的杂环，酯，酰胺和酮已成功用作CF 2来源。这种具有成本效益的铜（I）催化可方便地获得具有大量底物范围，宽泛的官能团耐受性和最高98％收率的高价值内酯。

  DOI：

  10.1021/acs.orglett.8b02069
• 作为产物：
  描述：

  在 氨 作用下， 以 水 为溶剂， 反应 0.5h， 以80%的产率得到2-(bromodifluoromethyl)-4-methylbenzoxazole
  参考文献：
  名称：

  Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  This paper reports the synthesis and antiviral properties of new difluoromethylbenzoxazole (DFMB) pyrimidine thioether derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. By use of a combination of structural biology study and traditional medicinal chemistry, several members of this novel class were synthesized using a single electron transfer chain process (radical nucleophilic substitution, Si) and were found to be potent against wild-type HIV-1 reverse transcriptase, with low cytotoxicity but with moderate activity against drug-resistant strains. The most promising compound 2,4 showed a significant EC50 value close to 6.4 nM against HIV-1 IIIB, a moderate EC50 value close to 54 mu M against an NNRTI resistant double mutant (K103N + Y181C), but an excellent selectivity index >15477 (CC50 > 100 mu M).

  DOI：

  10.1021/jm200766b

文献信息

• Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors
  作者：Jérémie Boyer、Eric Arnoult、Maurice Médebielle、Jérôme Guillemont、Johan Unge、Dirk Jochmans

  DOI：10.1021/jm200766b

  日期：2011.12.8

  This paper reports the synthesis and antiviral properties of new difluoromethylbenzoxazole (DFMB) pyrimidine thioether derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. By use of a combination of structural biology study and traditional medicinal chemistry, several members of this novel class were synthesized using a single electron transfer chain process (radical nucleophilic substitution, Si) and were found to be potent against wild-type HIV-1 reverse transcriptase, with low cytotoxicity but with moderate activity against drug-resistant strains. The most promising compound 2,4 showed a significant EC50 value close to 6.4 nM against HIV-1 IIIB, a moderate EC50 value close to 54 mu M against an NNRTI resistant double mutant (K103N + Y181C), but an excellent selectivity index >15477 (CC50 > 100 mu M).
• Copper(I)-Catalyzed Oxydifluoroalkylation of Alkenes: A Route to Functionalization of Lactones
  作者：Yang Da、Shengnan Han、Xiaoyong Du、Shaodong Liu、Lei Liu、Jie Li

  DOI：10.1021/acs.orglett.8b02069

  日期：2018.9.7

  An efficient copper(I)-catalyzed oxydifluoroalkylation of unsaturated carboxylic acids has been developed under mild reaction conditions. Various α-bromodifluoromethyl substituted heterocycles, esters, amides, and ketones were successfully employed as the CF2 source. This cost-effective copper(I) catalysis provides expedient access to high valued lactones with ample substrate scope, wide functional

  在温和的反应条件下，开发了一种有效的铜（I）催化的不饱和羧酸的氧二氟烷基化反应。各种α-溴二氟甲基取代的杂环，酯，酰胺和酮已成功用作CF 2来源。这种具有成本效益的铜（I）催化可方便地获得具有大量底物范围，宽泛的官能团耐受性和最高98％收率的高价值内酯。