4-(2,2-dibromovinyl)pyridine | 141368-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2,2-dibromovinyl)pyridine
• 英文别名: 4-(2,2-Dibromoethenyl)pyridine
• CAS: 141368-53-8
• 化学式: C₇H₅Br₂N
• 分子量: 262.931
• InChiKey: WZJZPTHZKDIMEF-UHFFFAOYSA-N

物化性质

• 沸点：
  286.6±25.0 °C(Predicted)
• 密度：
  1.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2,2-dibromovinyl)pyridine 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.5h， 生成 2,6-di-tert-butyl-4-(1-phenyl-4-(pyridin-4-yl)but-3-yn-1-yl)phenol
  参考文献：
  名称：

  Regioselective allenylation and propargylation of various para-quinone methides using alkynyl azaarenes as pronucleophiles

  摘要：

  我们开发了Brønsted碱介导的选择性区域性联芳基化和丙炔基化方法，使用未功能化的2-炔基氮杂芳烃作为原核亲核试剂，对各种para-喹啉甲烷进行反应。

  DOI：

  10.1039/d2cc03439e
• 作为产物：
  描述：

  3-吡啶甲醛 在 四溴化碳 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以71%的产率得到4-(2,2-dibromovinyl)pyridine
  参考文献：
  名称：

  ＺＮＦ１４３阻害活性を有する化合物およびその利用

  摘要：

  提供具有ZNF143抑制作用的化合物以及包含该化合物的ZNF143抑制剂和药物组合物。通过式（I）表示的化合物或其盐，以及包含它的ZNF143抑制剂和以其为有效成分的药物组合物。A-B-C-D（I）[其中A为氢、甲基、萘基、苯基或含氮杂环；B为，C为，含有酰胺键或含氮和氧的复杂芳香环；D为取代/未取代的苯基或含有单环的N或S的复杂芳香环；C和D均可具有取代基，也可以是融合的复杂环等]【选图】图1

  公开号：

  JP2016124812A

文献信息

• Cs₂CO₃-Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides
  作者：Yulei Wang、Jiepeng Gan、Liu Leo Liu、Hang Yuan、Yuxing Gao、Yan Liu、Yufen Zhao

  DOI：10.1021/jo500312n

  日期：2014.4.18

  trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.

  在无金属条件下开发了一种新颖且有效的Cs 2 CO 3促进的各种1,1,1-二溴-1-烯烃与容易获得的亚磷酸三烷基酯，乙基二苯基亚膦酸酯或二乙基苯基亚膦酸酯的磷酸化或亚膦酰基化，提供了实用而有效的方法一锅合成有价值的炔基膦酸酯，-次膦酸酯和-膦氧化物的工具，产率很高。
• Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (<i>Z</i>)-Alkenyl Compounds
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1021/jo9812781

  日期：1998.11.1

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.
• Synthesis and Evaluation of Efavirenz (SustivaTM) Analogues as HIV-1 Reverse Transcriptase Inhibitors: Replacement of the Cyclopropylacetylene Side Chain
  作者：Anthony J. Cocuzza、Dennis R. Chidester、Beverly C. Cordova、Susan Jeffrey、Rodney L. Parsons、Lee T. Bacheler、Susan Erickson-Viitanen、George L. Trainor、Soo S. Ko

  DOI：10.1016/s0960-894x(01)00192-5

  日期：2001.5

  Two series of efavirenz analogues have been developed: one in which the cyclopropane ring has been replaced by small heterocycles and another in which the entire acetylenic side chain has been replaced by alkyloxy groups. Several members of both series show equivalent potency to efavirenz against both wild-type virus and the key K103N mutant. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.
• Wright, J.; Milburn, G. H. W.; Shand, A. J., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 258, p. 1 - 14
  作者：Wright, J.、Milburn, G. H. W.、Shand, A. J.、Werninck, A. R.、Coles, H. J.、Smith, D. A. McL

  DOI：——

  日期：——
• MATERIALS AND METHODS USEFUL TO INDUCE CANCER CELL DEATH VIA METHUOSIS OR AUTOPHAGY OR A COMBINATION THEREOF
  申请人：The University of Toledo

  公开号：US20200297709A1

  公开（公告）日：2020-09-24

  Compounds, compositions, and methods useful for inducing cancer cell death via methuosis, autophagy, or a combination thereof, are described. The compounds have a 4-pyridyl group linked by a heterocyclic group to an aryl, heteroaryl, aralkyl, or heteroaryl alkyl.