4-Methyl-2-(trifluoromethyl)pyrrole | 137496-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-Methyl-2-(trifluoromethyl)pyrrole
• 英文别名: 1H-Pyrrole, 4-methyl-2-(trifluoromethyl)-；4-methyl-2-(trifluoromethyl)-1H-pyrrole
• CAS: 137496-31-2
• 化学式: C₆H₆F₃N
• mdl: MFCD18449452
• 分子量: 149.116
• InChiKey: VWDYJIKXAMEMGP-UHFFFAOYSA-N

物化性质

• 沸点：
  153.4±35.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-Methyl-5,6-dihydro-3-(trifluoromethyl)-6-(trimethylsiloxy)-4H-1,2-oxazine 在 hexacarbonyl molybdenum 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以51%的产率得到4-Methyl-2-(trifluoromethyl)pyrrole
  参考文献：
  名称：

  Efficient synthesis of trifluoromethyl-substituted 5,6-dihydro-4H-1,2-oxazines by the hetero-Diels-Alder reaction of 1,1,1-trifluoro-2-nitroso-2-propene and electron-rich olefins

  摘要：

  1,1,1-Trifluoro-2-nitroso-2-propene (1) was generated in situ by treatment of the alpha-bromo oxime 5 with base. Moderate to excellent yields of the 3-trifluoromethyl-substituted 1,2-oxazines 17-27 were obtained from the reaction of 1 and the silyl enol ethers 6-16, respectively. Other dienophiles, i.e., allyltrimethylsilane, cyclopentadiene, furan, and dihydropyran, upon reaction with 1 provided the cycloadducts 31-34, respectively, in good yield. The results demonstrated that 1 is probably the most reactive heterodiene that has so far been employed in this type of Diels-Alder reaction (i.e., Diels-Alder reaction with inverse electron demand). The mechanism of the reaction and diastereoselectivity of the cycloadditions are discussed. The reaction of 1 with indole and acetyl acetone afforded the oxime 38 and a mixture of the isomers 40-42, respectively. Also, ring openings and other transformations of the trifluoromethyl-substituted 1,2-oxazines were effected. Acid-induced desilylation of the silylated 1,2-oxazines provided oximes like 46 and 48 or 6-hydroxy-1,2-oxazines like 47. Treatment of the 1,2-oxazines with Mo(CO)6 in the presence of trifluoroacetic acid produced 2-trifluoromethyl-substituted pyrroles (e.g., 18 --> 50). The reduction of the 1,2-oxazines afforded either gamma-hydroxy oximes (e.g., 19 --> 51) or amino alcohols (e.g., 32 --> 52, 31 --> 55). The reduction of the indole derivative 38 by LiAlH4 provided the trifluoromethyl-substituted tryptamine 56. The results of these explorative studies demonstrated that readily available trifluoromethyl-substituted 1,2-oxazines could be efficiently converted into other compounds that bear a trifluoromethyl group.

  DOI：

  10.1021/jo00027a058

文献信息

• Pd(II)/Bu4NBr/DMSO Catalytic System for Practical Synthesis of Indoles and Pyrroles from Imines through Aerobic Dehydrogenative Cyclization
  作者：Naohiko Yoshikai、Wei Tan、Xiaoya Hou

  DOI：10.1055/s-0034-1379208

  日期：——

  scales (up to 55 mmol). N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole derivatives, respectively, in moderate to good yields. The reactions are operationally simple and can be readily performed on multigram

  摘要 ñ -芳基-和Ñ -allylimines通常衍生自取代的苯乙酮经历钯（II）在四丁基溴化铵和分子氧在DMSO存在下得到的吲哚并吡咯衍生物，分别催化的脱氢环化反应，在中度至良好的产率。该反应操作简单，可以容易地以克级（最高55 mmol）进行。 ñ -芳基-和Ñ -allylimines通常衍生自取代的苯乙酮经历钯（II）在四丁基溴化铵和分子氧在DMSO存在下得到的吲哚并吡咯衍生物，分别催化的脱氢环化反应，在中度至良好的产率。该反应操作简单，可以容易地以克级（最高55 mmol）进行。
• [EN] HETEROCYCLIC DERIVATIVE AND MEDICAL APPLICATION THEREOF<br/>[FR] DÉRIVÉ HÉTÉROCYCLIQUE ET SON APPLICATION MÉDICALE<br/>[ZH] 一种杂环衍生物及其在医药上的应用
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2022078305A1

  公开（公告）日：2022-04-21

  一种通式(I)所述的化合物或者其立体异构体、互变异构体、氘代物、溶剂化物、前药、代谢产物、药学上可接受的盐或共晶，及其中间体和制备方法，以及在制备治疗与JAK激酶活性或表达量相关疾病的药物中的应用。
• [EN] BENZIMIDAZOLE COMPOUNDS AND USE THEREOF FOR TREATING ALZHEIMER'S DISEASE OR HUNTINGTON'S DISEASE<br/>[FR] COMPOSÉS DE BENZIMIDAZOLE ET LEUR UTILISATION POUR TRAITER LA MALADIE D'ALZHEIMER OU LA MALADIE DE HUNTINGTON
  申请人：SHIH CHUAN

  公开号：WO2020047360A1

  公开（公告）日：2020-03-05

  Benzimidazole compounds of formula (I), shown below, are disclosed. The compounds are potent human glutaminyl cyclase inhibitors. Also disclosed is a pharmaceutical composition containing one of these compounds and a pharmaceutical acceptable carrier, as well as a method of treating Alzheimer's disease or Huntington's disease by administering to a subject in need thereof an effective amount of such a compound.