6-chloro-2,3′-bipyridine | 39883-45-9

• 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: 6-chloro-2,3′-bipyridine
• 英文别名: 2-Chloro-6-(3-pyridyl)pyridine；6-chloro-[2,3']bipyridinyl；2-Chlor-6-(3-pyridyl)-pyridin；2-Chloro-6-(pyridin-3-yl)pyridine；2-chloro-6-pyridin-3-ylpyridine
• CAS: 39883-45-9
• 化学式: C₁₀H₇ClN₂
• 分子量: 190.632
• InChiKey: UCUYYVLLYRTQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-2,3′-bipyridine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-chloro-6-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)pyridine
  参考文献：
  名称：

  Synthesis, Analgesic Activity, and Binding Properties of Some Epibatidine Analogs with a Tropine Skeleton

  摘要：

  A series of epibatidine analogs and their positional isomers bearing an 8-azabicyclo[3.2.1]octane moiety is described. Also some of their simplified analogs bearing a 3-piperidine moiety are reported. Their receptor binding profiles (5-HT1A, 5-HT1B, M1, M2, neuronal nicotinic receptor) and analgesic activity (hot plate, acetic acid induced writhing) have been studied. Some of the compounds, especially those containing an 8-azabicyclo[3.2.1]oct-2-ene moiety possess high afinity for the nicotinic cholinergic receptor. The most analgesically active compounds are also highly toxic. Optimized structures (PM3-MOPAC, Alchemy 2000, Tripos Inc.) of compounds 1-9 were compared with that of epibatidine.

  DOI：

  10.1002/1521-4184(20006)333:6<167::aid-ardp167>3.0.co;2-8
• 作为产物：
  描述：

  (2E,4Z)-2-Cyano-5-dimethylamino-5-pyridin-3-yl-penta-2,4-dienoic acid tert-butyl ester 在 盐酸 、 溶剂黄146 作用下， 反应 96.0h， 以77%的产率得到6-chloro-2,3′-bipyridine
  参考文献：
  名称：

  New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines

  摘要：

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.

  DOI：

  10.1021/jo00117a029

文献信息

• Micelle-Enabled Suzuki–Miyaura Cross-Coupling of Heteroaryl Boronate Esters
  作者：Pengfei Guo、Hao Zhang、Jianguang Zhou、Fabrice Gallou、Michael Parmentier、Hui Wang

  DOI：10.1021/acs.joc.8b00257

  日期：2018.7.20

  Suzuki–Miyaura cross-coupling of heteroaryl boronic esters with aryl or heteroaryl halides. The micellar catalysis enables this coupling reaction to run under mild conditions, which avoids the decomposition of heteroaryl boronate esters and allows for high chemoselectivity for cross-coupling reaction with 6-chloropridine-2-boronic ester. The micellar protocol expands the scope of the cross-coupling reaction

  我们报告了杂芳基硼酸酯与芳基或杂芳基卤化物的铃木-宫浦交叉偶联的胶束协议。胶束催化使该偶联反应能够在温和的条件下进行，从而避免了杂芳基硼酸酯的分解，并为与6-氯吡啶-2-硼酸酯的交叉偶联反应提供了高化学选择性。胶束方案扩大了具有挑战性的杂芳基硼酸酯的交叉偶联反应的范围，并补充了用于构建杂联二芳基结构单元的现有交叉偶联方法。
• Saponin: a green and efficient natural surfactant for Suzuki–Miyaura cross-couplings of heteroaryl substrates in aqueous media at ambient conditions
  作者：Vinothkumar Vinayagam、Subir Kumar Sadhukhan、Sreenivasa Reddy Kasu、Ravi Kumar Maroju、Tanguturi Venkatanarayana Hajay Kumar、Satish Kumar Karre、Dhurwasulu Baledi

  DOI：10.1039/d3gc04757a

  日期：——

  Herein, we report a commercially available natural saponin acting as a surfactant and serving as a micellar catalyst, enabling Suzuki–Miyaura cross-coupling effectively with highly challenging heteroaromatic substrates in water at room temperature.

  在此，我们报告了一种市售天然皂甙，它既是一种表面活性剂，又是一种胶束催化剂，可在室温下有效地与水中极具挑战性的杂芳香族底物发生铃木-宫浦交叉偶联反应。
• Synthesis, Analgesic Activity, and Binding Properties of Some Epibatidine Analogs with a Tropine Skeleton
  作者：Stanislav Rádl、Wieland Hafner、Milo Budeaínsky、Lucie Hejnová、Ivan Krejcí

  DOI：10.1002/1521-4184(20006)333:6<167::aid-ardp167>3.0.co;2-8

  日期：2000.6

  A series of epibatidine analogs and their positional isomers bearing an 8-azabicyclo[3.2.1]octane moiety is described. Also some of their simplified analogs bearing a 3-piperidine moiety are reported. Their receptor binding profiles (5-HT1A, 5-HT1B, M1, M2, neuronal nicotinic receptor) and analgesic activity (hot plate, acetic acid induced writhing) have been studied. Some of the compounds, especially those containing an 8-azabicyclo[3.2.1]oct-2-ene moiety possess high afinity for the nicotinic cholinergic receptor. The most analgesically active compounds are also highly toxic. Optimized structures (PM3-MOPAC, Alchemy 2000, Tripos Inc.) of compounds 1-9 were compared with that of epibatidine.
• New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines
  作者：Robert Church、Ronald Trust、J. Donald Albright、Dennis Powell

  DOI：10.1021/jo00117a029

  日期：1995.6

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.