2-chloro-6-(2-thienyl)pyridine | 35299-70-8

• 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: 2-chloro-6-(2-thienyl)pyridine
• 英文别名: 2-Chloro-6-(thiophen-2-yl)pyridine；2-chloro-6-thiophen-2-ylpyridine
• CAS: 35299-70-8
• 化学式: C₉H₆ClNS
• 分子量: 195.672
• InChiKey: WEULMRIZISAQOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  304.7±27.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(2-thienyl)pyridine 在 吡啶 、 sodium tetrahydroborate 、 1,10-菲罗啉 、 nickel diacetate 作用下， 生成 2-(2-噻吩基)吡啶
  参考文献：
  名称：

  A Micellar Catalysis Strategy for Suzuki–Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: No Copper, in Water, Very Mild Conditions

  摘要：

  Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.

  DOI：

  10.1021/acscatal.7b03241
• 作为产物：
  描述：

  2,6-二氯吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 氢碘酸 、 sodium carbonate 、 sodium iodide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 2-chloro-6-(2-thienyl)pyridine
  参考文献：
  名称：

  Desymmetrization of dichloroazaheterocycles

  摘要：

  3,6-Dichloropyridizine 1a was converted in good;yield into its mono-iodo derivative 1b when treated with a mixture of hydriodic acid and sodium iodide. Pure samples of the mono-iodo derivatives 2b, 3b and 4b could not be obtained from their corresponding dichlorinated precursors with these reagents. Compounds Ib and 4b underwent palladium catalysed Suzuki, Sonogashira and other coupling reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00961-8

文献信息

• Mixed heteroarene oligomers
  作者：Akio Minato、Keizo Suzuki、Kohei Tamao、Makoto Kumada

  DOI：10.1039/c39840000511

  日期：——

  Various types of mixed heteroatene oligomers can be readily prepared from heteroarene dihalides via stepwise coupling with heteroaryl Grignard reagents catalysed by a palladium–phosphine complex.

  杂芳烃二卤化物可通过与钯-膦配合物催化的杂芳基格氏试剂逐步偶联而容易地制备出各种类型的杂芳烃低聚物。
• Process for producing 2-substituted pyridine derivative
  申请人：Koyakumaru Kenichi

  公开号：US20060041142A1

  公开（公告）日：2006-02-23

  The present invention provides a method of producing a pyridine derivative having a substituent at the 2-position of a heterocyclic structure conveniently and with fine selectivity. The present invention relates to a production method of a pyridine derivative having a substituent at the 2-position of a heterocyclic structure, which is represented by the formula (III), which includes reacting a 2-sulfonylpyridine derivative of the formula (I) with an organometallic compound of the formula (II) and the like, and the like: wherein each symbol is as defined in the Description.

  本发明提供了一种生产在杂环结构的 2 位上具有取代基的吡啶衍生物的方法，该方法简便且选择性好。本发明涉及一种在杂环结构的 2 位上具有取代基的吡啶衍生物的生产方法，该衍生物由式（III）表示，其中包括将式（I）的 2-磺酰基吡啶衍生物与式（II）的有机金属化合物等反应： 其中各符号如说明书中所定义。
• Kauffmann, Thomas; Mitschker, Alfred; Woltermann, Annegret, Chemische Berichte, 1983, vol. 116, # 3, p. 992 - 1000
  作者：Kauffmann, Thomas、Mitschker, Alfred、Woltermann, Annegret

  DOI：——

  日期：——
• Kauffmann,T. et al., Angewandte Chemie, 1971, vol. 83, p. 796 - 798
  作者：Kauffmann,T. et al.

  DOI：——

  日期：——
• Kauffmann,T. et al., Angewandte Chemie, 1972, vol. 84, # 17, p. 828 - 829
  作者：Kauffmann,T. et al.

  DOI：——

  日期：——