3-(5-chlorothiophen-2-yl)pyridine | 859239-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-(5-chlorothiophen-2-yl)pyridine
• CAS: 859239-16-0
• 化学式: C₉H₆ClNS
• 分子量: 195.672
• InChiKey: ICAMVATULJAWLY-UHFFFAOYSA-N

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

• 作为产物：
  描述：

  2-氯噻吩 、 3-溴吡啶 在 C₄₂H₃₆Cl₂N₂Pd 、 potassium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以91%的产率得到3-(5-chlorothiophen-2-yl)pyridine
  参考文献：
  名称：

  刚性α-二亚胺钯配合物作为噻吩和杂芳基溴化物的直接 CH 芳基化预催化剂

  摘要：

  描述了由刚性α-二亚胺钯配合物促进的噻吩的直接 CH 杂芳基化。这种方法表现出广泛的底物范围和官能团耐受性，并继续形成区域选择性产物。

  DOI：

  10.1016/j.inoche.2022.109403

文献信息

• Bulky α-diimine palladium complexes: highly efficient for direct C–H bond arylation of heteroarenes under aerobic conditions
  作者：Jia-Sheng Ouyang、Yan-Fang Li、Dong-Sheng Shen、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1039/c6dt02544g

  日期：——

  bidentate N,N-palladium complex C3 with both a backbone and N-aryl bulkiness was found to be a highly efficient precatalyst under aerobic conditions. With a low palladium loading of 0.5–0.1 mol%, a variety of heteroarenes with challenging bulky steric aryl bromides as well as heteroaryl bromides are all applicable for this cross-coupling reaction.

  通过增强主链和N-芳基部分的体积的策略，我们设计并合成了一种体积较大的α-二亚胺钯配合物（即[Ar–N C（R）–C（R）N– Ar] PdCl 2，（Ar ＝ 2-苯甲酰基-4，6-二甲基苯基）}，C1，R ＝ H；C2，R ＝ An；C3，R ＝ Ph）。这些钯配合物的结构已得到很好的表征，而C1和C3则通过X射线衍射进一步表征。对杂芳烃的直接CH键芳构化筛选了预催化剂的催化性能。二齿N，N-钯络合物C3与两个主链和ñ -芳基膨松性被发现是在有氧条件下高效率的预催化剂。钯负载量低至0.5-0.1 mol％，各种具有挑战性的庞大的空间芳基溴化物和杂芳基溴化物的杂芳烃都适用于这种交叉偶联反应。
• Bis(imino)acenaphthene (BIAN)-Supported <i>N</i>-Heterocyclic Carbene Palladium Complexes with Ancillary Ligands: Readily Activated Precatalysts for Direct C–H Arylation of Thiophenes
  作者：Di-Zhong Zheng、Dong-Hui Li、Huan Liu、Youxiang Shao、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.organomet.2c00007

  日期：2022.4.25

  thiophenes with (hetero)aryl bromides by bulky bis(imino)acenaphthene (BIAN)-supported N-heterocyclic carbene palladium complexes. The relationship between the structure of palladium complexes with ancillary ligands and catalytic properties was discussed. Upon a low palladium loading of 0.01–0.05 mol %, the bulky palladium complex was successfully used to catalyze the cross-coupling of a variety of thiophens

  我们在此报告了通过庞大的双（亚氨基）苊（BIAN）负载的N将噻吩与（杂）芳基溴化物的高效直接 C-H 芳基化-杂环卡宾钯配合物。讨论了钯与辅助配体的结构与催化性能之间的关系。在 0.01-0.05 mol% 的低钯负载量下，庞大的钯络合物成功地用于在有氧条件下催化各种噻吩与（杂）芳基溴化物的交叉偶联。此外，它提供了一种在好氧反应条件下获得具有高分子量和高 HT 值的聚 (3-己基噻吩) 的实用且直接的途径。为了了解转化机制，对直接芳基化进行了实验研究和 DFT 计算，这支持了 Pd (0) /Pd (II) CMD 过程的参与。
• Synthetic Compounds and Derivatives as Modulators of Smoking or Nicotine Ingestion and Lung Cancer
  申请人：Cashman John R.

  公开号：US20080188527A1

  公开（公告）日：2008-08-07

  Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

  本发明涉及选择性抑制细胞色素P-450 2A6（CYP2A6）、选择性抑制细胞色素P-450 2A13（CYP2A13）和/或选择性调节尼古丁乙酰胆碱受体（nAChR）的尼古丁相关化合物。本发明还涉及包含本发明化合物的制药组合物，以及使用该制药组合物治疗或预防与尼古丁摄入相关的疾病或障碍，或可通过选择性调节nAChR进行治疗的疾病或障碍的方法。
• SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
  申请人：Cashman John R.

  公开号：US20100298345A1

  公开（公告）日：2010-11-25

  Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

  本发明涉及选择性抑制细胞色素P-450 2A6（CYP2A6）的尼古丁相关化合物，选择性抑制细胞色素P-450 2A13（CYP2A13），和/或选择性调节尼古丁乙酰胆碱受体（nAChR）。本发明还涉及包含本发明化合物的制药组合物，以及使用该制药组合物治疗或预防与尼古丁摄入有关的疾病或障碍，或者通过选择性调节nAChRs进行治疗的疾病或障碍的方法。
• Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
  作者：Bao-Tian Luo、Huan Liu、Zhi-Jie Lin、Jingxing Jiang、Dong-Sheng Shen、Rui-Zhi Liu、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.organomet.5b00181

  日期：2015.10.26

  In the present work, a series of alpha-hydroxyimine palladium complexes with bulky substituents (i.e., [Ar-N=C(R)-C(R)(2)-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylinethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.