2-(4-(trifluoromethyl)phenyl)pyrazine | 380626-88-0

• 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-(4-(trifluoromethyl)phenyl)pyrazine
• 英文别名: 2-(4-trifluoromethylphenyl)pyrazine；2-[4-(trifluoromethyl)phenyl] pyrazine；2-[4-(trifluoromethyl)phenyl]pyrazine
• CAS: 380626-88-0
• 化学式: C₁₁H₇F₃N₂
• 分子量: 224.185
• InChiKey: QLIZFCCVOYTJQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  269.5±35.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C，干燥密封保存。

反应信息

• 作为反应物：
  描述：

  2-(4-(trifluoromethyl)phenyl)pyrazine 在 醋酸钯 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 2-(4-三氟甲基苯基)-哌嗪
  参考文献：
  名称：

  Piperidines and related compounds for treatment of alzheimer's disease

  摘要：

  公式I的化合物：选择性地抑制Aβ（1-42）的产生，因此在治疗或预防与β-淀粉样蛋白在大脑中沉积相关的疾病中是有用的。

  公开号：

  US07638629B2
• 作为产物：
  描述：

  吡嗪 、 [[4-(Trifluoromethyl)phenyl]-(2,4,6-trimethoxyphenyl)-lambda3-iodanyl] trifluoromethanesulfonate 在 sodium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 10.0h， 以53%的产率得到2-(4-(trifluoromethyl)phenyl)pyrazine
  参考文献：
  名称：

  Selective Aryl Radical Transfers into N-Heteroaromatics from Diaryliodonoium Salts with Trimethoxybenzene Auxiliary

  摘要：

  We have found that a series of trimethoxybenzene-based diaryl-iodonium(III) salts I (ArI+Ar'X-, where Ar = various aryl groups, Ar' = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar') as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar') coupling product.

  DOI：

  10.3987/com-16-s(s)90

文献信息

• Electrochemical oxidation synergizing with Brønsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines
  作者：Kun Liu、Chunlan Song、Jiarong Wu、Yuqi Deng、Shan Tang、Aiwen Lei

  DOI：10.1039/c8gc03786h

  日期：——

  Electrochemical oxidative [4 + 2] annulation for the synthesis of pyrazines.

  电化学氧化[4 + 2]环化合成吡嗪。
• Synthesis of Chiral Piperazines via Hydrogenation of Pyrazines Activated by Alkyl Halides
  作者：Wen-Xue Huang、Lian-Jin Liu、Bo Wu、Guang-Shou Feng、Baomin Wang、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.6b01190

  日期：2016.7.1

  A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted ones with up to 96% ee. The high enantioselectivity, easy scalability, and concise drug synthesis demonstrate the practical utility.

  已经开发了一种简便的方法，用于通过烷基卤化物活化的吡嗪的Ir催化加氢合成手性哌嗪，从而得到了广泛的手性哌嗪，包括3-取代的2,3和3,5-二取代的ee高达96％。高对映选择性，易扩展性和简洁的药物合成证明了其实用性。
• Direct, Catalytic, and Regioselective Synthesis of 2-Alkyl-, Aryl-, and Alkenyl-Substituted <i>N</i>-Heterocycles from <i>N</i>-Oxides
  作者：Oleg V. Larionov、David Stephens、Adelphe Mfuh、Gabriel Chavez

  DOI：10.1021/ol403631k

  日期：2014.2.7

  A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural

  描述了杂环N-氧化物一步转化为 2-烷基-、芳基-和烯基-取代的N-杂环。这种广泛方法的成功取决于铜催化和氟化锂或氯化镁活化的结合。这种方法在复杂N-杂环的后期修饰中的效用可以通过几种抗疟、抗微生物和杀真菌剂的新结构类似物的简便合成来举例说明。
• Iron-catalyzed Cross-Coupling of Electron-Deficient Heterocycles and Quinone with Organoboron Species via Innate C–H Functionalization: Application in Total Synthesis of Pyrazine Alkaloid Botryllazine A
  作者：Parvinder Pal Singh、Sravan Kumar Aithagani、Mahipal Yadav、Varun Pratap Singh、Ram A. Vishwakarma

  DOI：10.1021/jo302797r

  日期：2013.3.15

  innate C–H functionalization. Iron(II) acetylacetonate along with oxidant (K2S2O8) and phase-transfer catalyst (TBAB) under open flask conditions efficiently catalyzed the cross-coupling of pyrazine with arylboronic acids and gave monoarylated products in good to excellent yields. Optimized conditions also worked for other heterocylces such as quinoxalines, pyridines, quinoline, and isoquinoline as

  在这里，我们报告一个铁催化的交叉-通过先天C-H官能缺电子杂环的偶联反应和醌与有机硼物种。铁（II）与氧化剂（K沿着乙酰丙酮2小号2 ö 8）和相转移催化剂（TBAB）打开烧瓶的条件下有效地催化交叉-与芳基硼酸吡嗪耦合又给monoarylated产品以良好至优异的产量。优化的条件也适用于其他杂环，例如喹喔啉，吡啶，喹啉和异喹啉以及醌。此外，作为第一个实例，我们证明了其在合成抗癌海洋吡嗪生物碱结晶苦菜碱A中的应用。
• PYRIDINIUM SALT AND PEST CONTROL AGENT
  申请人：Nippon Soda Co., Ltd.

  公开号：US20200275655A1

  公开（公告）日：2020-09-03

  A compound represented by formula (I) or formula (II): wherein, A represents an oxygen atom or a sulfur atom; X 1 represents a halogeno group, a substituted or unsubstituted C 1-6 alkyl group and so on; m represents the number of X 1 and is any integer of 0 to 5; any two of X 1 may be bound together to form a bivalent hydrocarbon group; Y represents a single bond or a substituted or unsubstituted C 2-6 alkenylene group; Q 1 represents a substituted or unsubstituted C 6-10 arylene group or a substituted or unsubstituted 6- to 10-membered heteroarylene group; Q 2 represents a substituted or unsubstituted C 6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group; Z q− represents a counter ion; and q represents a valence of the counter ion and is 1 or 2.

  化合物的化学式为(I)或(II)：其中，A代表氧原子或硫原子；X1代表卤素基团、取代或未取代的C1-6烷基基团等；m代表X1的数量，为0至5的任意整数；任意两个X1可以结合形成二价的碳氢化合物基团；Y代表单键或取代或未取代的C2-6烯基基团；Q1代表取代或未取代的C6-10芳基基团或取代或未取代的6-到10元杂环芳基基团；Q2代表取代或未取代的C6-10芳基基团或取代或未取代的5-到6元杂环芳基基团；Zq-代表计数离子；q代表计数离子的价数，为1或2。