2-(二氟甲基)-1,3-苯并恶唑 | 91437-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 2-(二氟甲基)-1,3-苯并恶唑
• 英文名称: 2-(Difluoromethyl)benzoxazole
• 英文别名: (difluoromethyl)benzoxazole；2-Difluoromethyl-benzoxazole；2-(difluoromethyl)-1,3-benzoxazole
• CAS: 91437-09-1
• 化学式: C₈H₅F₂NO
• 分子量: 169.131
• InChiKey: UDIPXWGWAFYJOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为产物：
  描述：

  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 1.5h， 以89%的产率得到2-(二氟甲基)-1,3-苯并恶唑
  参考文献：
  名称：

  卤代-二氟甲基芳族化合物和杂环的合成与反应性：在合成宝石-二氟生物活性化合物中的应用

  摘要：

  为了制备对HIV有活性的新型含氟化合物，并基于一系列溴代二氟甲基化合物的电化学还原反应，发现四（二甲基氨基）乙烯（TDAE）是2-（溴二氟甲基）苯并恶唑1和5-（溴二氟甲基）-3-苯基-1,2,4-恶二唑3。假定在该反应中发生了以二氟甲基为中间体的逐步电子转移。在温和的条件下，生成的二氟甲基杂环阴离子被芳香族和杂环醛7 – 14和酮15 – 16有效捕获。以这种方式，相应的β，β-二氟α-heteroarylated醇17 - 32在适度得到良好的产率。相同的方法被成功地应用于chlorodifluoromethylated酮的还原4 - 6和所产生的α，α-二氟乙酰基阴离子被截留与几个醛7，8，10，11，在温和的条件下，得到相应的2,2-二氟-3-羟基酮衍生物33 – 38，产率中等。2-（溴二氟甲基）苯并恶唑的S RN 1反应（1）与杂环硫醇和酚类化合物的阴离子也进行了。测试了均带有CF

  DOI：

  10.1016/s0022-1139(01)00378-5

文献信息

• Direct <i>gem</i>-difluoromethylenation of sp³-hybridized carbon center through copper-mediated radical/radical cross-coupling for the construction of a CH₂–CF₂ linkage
  作者：Haizhen Jiang、Minjun Xu、Wenjun Lu、Wenfeng Tian、Wen Wan、Yunrong Chen、Hongmei Deng、Shaoxiong Wu、Jian Hao

  DOI：10.1039/c5cc05677b

  日期：——

  An efficient gem-difluoromethylenation of benzyl bromides through copper-mediated direct radical/radical C–C cross-coupling has been developed for the construction of CH₂–CF₂ linkage.

  通过铜介导的直接自由基/自由基C-C交叉偶联，已开发出一种高效的苄溴化物-二氟甲亚甲基化合物的构建方法，用于构建CH2-CF2键合。
• Single electron transfer approaches to the practical synthesis of aromatic and heterocyclic-CF2H derivatives
  作者：William R Dolbier、Maurice Médebielle、Samia Ait-Mohand

  DOI：10.1016/s0040-4039(01)00873-5

  日期：2001.7

  Single electron transfer (SET) approaches with organic reductants such as sodium hydroxymethanesulfinate (Rongalite®), sodium dithionite (regarded as precursors of sulfoxylate radical anion) and tetrakis(dimethylamino)ethylene (TDAE) were employed for the reductive dehalogenation of a series of halogeno-difluoromethylated aromatics and heterocycles, and for the practical synthesis of the corresponding

  使用有机还原剂（例如羟甲亚磺酸钠（Rongalite®），连二亚硫酸钠（被视为亚硫酸根自由基阴离子的前体）和四（二甲基氨基）乙烯（TDAE））进行单电子转移（SET）方法用于一系列卤代化合物的还原脱卤。 -二氟甲基化的芳族化合物和杂环，并用于实际合成相应的二氟甲基化的衍生物。
• One-pot synthesis of 2-trifluoromethyl and 2-difluoromethyl substituted benzo-1,3-diazoles
  作者：Fenglian Ge、Zengxue Wang、Wen Wan、Wencong Lu、Jian Hao

  DOI：10.1016/j.tetlet.2007.03.015

  日期：2007.4

  2-Trifluoromethyl and 2-difluoromethyl substituted benzimidazole, benzoxazole and benzothiazole derivatives were efficiently prepared through a one-pot reaction of trifluoroacetic acid and difluoroacetic acid, respectively, with commercially available o-phenylenediamines, 2-aminophenols, and 2-aminobenzenethiols in good to excellent yields. Subsequential bromination of 2-difluoromethyl groups by photolysis

  通过三锅法分别将三氟乙酸和二氟乙酸与市售的邻苯二胺，2-氨基酚和2-氨基苯硫醇进行一锅反应，可有效地制备2-三氟甲基和2-二氟甲基取代的苯并咪唑，苯并恶唑和苯并噻唑衍生物。优异的产量。通过NBS光解法对2-二氟甲基进行的后续溴化反应导致形成溴二氟甲基苯并-1,3-二唑，可用于制备新一代的与宝石-二氟亚甲基连接的相同或不同的双分子用于药物合成。
• 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.
• LISKA, FRANTISEK;VAGNER, JOSEF;DEDEK, VACLAV, SB. VSCHT PRAZE, 29,(1986) 37-43
  作者：LISKA, FRANTISEK、VAGNER, JOSEF、DEDEK, VACLAV

  DOI：——

  日期：——