2-氯-6-(甲基硫代)吡啶 | 77145-64-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-氯-6-(甲基硫代)吡啶
• 中文别名: 2-氯-6-甲基硫代吡啶
• 英文名称: 2-chloro-6-(methylthio)pyridine
• 英文别名: 2-chloro-6-methylsulfanylpyridine
• CAS: 77145-64-3
• 化学式: C₆H₆ClNS
• mdl: MFCD00173422
• 分子量: 159.639
• InChiKey: KVYNCXZSIHYSDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-氯-6-(甲基硫代)吡啶 在 双氧水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-氯-6-乙氧基吡啶
  参考文献：
  名称：

  Furukawa, Naomichi; Ogawa, Satoshi; Kawai, Tsutomu, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1839 - 1845

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯吡啶 在 正丁基锂 、 N,N-二甲基乙醇胺 作用下， 以 正己烷 为溶剂， 反应 3.25h， 生成 2-氯-6-(甲基硫代)吡啶
  参考文献：
  名称：

  Lithiation of 2-Heterosubstituted Pyridines with BuLi−LiDMAE:  Evidence for Regiospecificity at C-6

  摘要：

  The determination of the initial deprotonation site of 2-chloro- and 2-methoxypyridine during reaction with BuLi-LiDMAE has been investigated. A series of experiments on deuterated regioisomers revealed a direct lithiation at C-6 excluding a potential first classical ortholithiation and lithium equilibration in the reaction medium. These results suggested that the formation of lithium aggregates at the neighboring of the pyridinic nitrogen atom favored BuLi delivery at C-6 as well as 6-lithio intermediate stabilization.

  DOI：

  10.1021/jo015855o

文献信息

• N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20100298334A1

  公开（公告）日：2010-11-25

  The present invention relates to N-(hetero)aryl-pyrrolidine derivatives of Formula I: which are JAK inhibitors, such as selective JAK1 inhibitors, useful in the treatment of JAK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及式I的N-(杂)芳基吡咯烷衍生物： 这些是JAK抑制剂，如选择性JAK1抑制剂，在治疗JAK相关疾病方面具有用处，例如炎症和自身免疫性疾病，以及癌症。
• α-Heteroarylation of Thioethers via Photoredox and Weak Brønsted Base Catalysis
  作者：Edwin Alfonzo、Sudhir M. Hande

  DOI：10.1021/acs.orglett.1c02151

  日期：2021.8.6

  thioethers to α-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of α-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by α-C–H deprotonation by a weak Brønsted base catalyst to afford α-thio alkyl radicals. Further,

  我们报告了硫醚对 α-硫代烷基自由基的 C-H 活化以及它们与N-甲氧基杂芳鎓盐的加成，用于氧化还原中性合成 α-杂芳族硫醚。研究与两步活化机制一致，其中通过光氧化还原催化剂将硫醚氧化为硫化物自由基阳离子，然后通过弱 Brønsted 碱催化剂进行 α-C-H 去质子化以提供 α-硫代烷基自由基。此外，N-甲氧基杂芳鎓盐作为甲氧基自由基的来源，有助于α-硫代烷基自由基的产生和再生光氧化还原催化循环的牺牲氧化剂，发挥了额外的作用。
• Unusual C-6 Lithiation of 2-Chloropyridine-Mediated by BuLi−Me₂N(CH₂)₂OLi. New Access to 6-Functional-2-chloropyridines and Chloro-bis-heterocycles
  作者：Sabine Choppin、Philippe Gros、Yves Fort

  DOI：10.1021/ol005538o

  日期：2000.3.1

  the loss of chlorine atom while exclusive directed ortho metalation is obtained using LDA. Herein it is shown that the BuLi-Me(2)N(CH(2))(2)OLi (BuLi-LiDMAE) superbase promotes an unprecedented regioselective C-6 lithiation. The method was successfully applied to the preparation of potentially useful chlorinated pyridinic and bis-heterocyclic synthons.

  2-氯吡啶与烷基ith的反应通常导致亲核加成，导致氯原子的损失，同时使用LDA获得排他性的直接邻位金属化。在此表明，BuLi-Me（2）N（CH（2））（2）OLi（BuLi-LiDMAE）超碱促进了前所未有的区域选择性C-6锂化。该方法已成功地用于制备潜在有用的氯化吡啶二酮和双杂环合成子。
• One-pot double functionalisation of π-deficient heterocyclic lithium reagents
  作者：Anthony Chartoire、Corinne Comoy、Yves Fort

  DOI：10.1039/c0ob00734j

  日期：——

  Herein, we report an efficient method for the double functionalisation of lithiated halogenopyridines, -pyrazines or -furopyridines through a convenient one-pot electrophilic trapping/nucleophilic substitution sequence.

  在此，我们报道了一种高效的方法，通过便捷的一锅法亲电捕获/亲核取代序列，实现锂化卤代吡啶、吡嗪或呋喃吡啶的双功能化。
• Oxadiazolopyridine Derivates for Use as Ghrelin O-Acyl Transferase (GOAT) Inhibitors
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20180037594A1

  公开（公告）日：2018-02-08

  The present invention relates to compounds of general formula I, wherein the groups R 1 , R 2 and n are defined as in claim 1 , which have valuable pharmacological properties, in particular bind to ghrelin O-acyl transferase (GOAT) and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular obesity.

  本发明涉及通式I的化合物，其中基团R1、R2和n的定义如权利要求书中所述，该化合物具有有价值的药理学特性，特别是结合到生长激素释放激素酰基转移酶（GOAT）并调节其活性。这些化合物适用于治疗和预防可能受该受体影响的疾病，如代谢性疾病，特别是肥胖症。