5-azido-6-chloropyridin-3-ylmethanol | 321845-14-1

• 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: 5-azido-6-chloropyridin-3-ylmethanol
• 英文别名: (5-Azido-6-chloropyridin-3-yl)methanol
• CAS: 321845-14-1
• 化学式: C₆H₅ClN₄O
• 分子量: 184.585
• InChiKey: GCEDRSRXIMQECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azido-6-chloropyridin-3-ylmethanol 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以85%的产率得到5-azido-6-chloropyridin-3-ylmethyl chloride
  参考文献：
  名称：

  5-Azidoimidacloprid and an Acyclic Analogue as Candidate Photoaffinity Probes for Mammalian and Insect Nicotinic Acetylcholine Receptors

  摘要：

  The 5-azido analogue:of:the major, insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethy)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N'-methyl-N " -nitroguanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two: ways: from, 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide: followed by,chlorine substitution of morpholine with Ethyl chloroformate: Coupling of 3 with 2-nitroiminoimidazolidine gave 1, Conversion of 3 to 2 was achieved in good,yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in land 2 increases' the affinity 7-79-fold for rat brain and recombinant (alpha4 beta2 nAChRs:(K(i)s 4.4-60 nM competing with [H-3](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (K(i)s 1-5 nM competing with [H-3]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization. of both mammalian and insect receptors.

  DOI：

  10.1021/jm000240p
• 作为产物：
  描述：

  5-硝基-6-氯烟酸 在 盐酸 、 dimethyl sulfide borane 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 5.27h， 生成 5-azido-6-chloropyridin-3-ylmethanol
  参考文献：
  名称：

  5-Azidoimidacloprid and an Acyclic Analogue as Candidate Photoaffinity Probes for Mammalian and Insect Nicotinic Acetylcholine Receptors

  摘要：

  The 5-azido analogue:of:the major, insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethy)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N'-methyl-N " -nitroguanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two: ways: from, 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide: followed by,chlorine substitution of morpholine with Ethyl chloroformate: Coupling of 3 with 2-nitroiminoimidazolidine gave 1, Conversion of 3 to 2 was achieved in good,yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in land 2 increases' the affinity 7-79-fold for rat brain and recombinant (alpha4 beta2 nAChRs:(K(i)s 4.4-60 nM competing with [H-3](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (K(i)s 1-5 nM competing with [H-3]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization. of both mammalian and insect receptors.

  DOI：

  10.1021/jm000240p

文献信息

• BICYCLIC ENAMINO(THIO)CARBONYL COMPOUNDS
  申请人：Jeschke Peter

  公开号：US20090181947A1

  公开（公告）日：2009-07-16

  The present invention relates to novel bicyclic enamino(thio)carbonyl compounds, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本发明涉及新颖的双环烯胺基(硫)酰基化合物，以及其制备方法和用于控制动物害虫，特别是节肢动物，尤其是昆虫的用途。
• SUBSTITUTED ENAMINOCARBONYL COMPOUNDS USED AS INSECTICIDES
  申请人：Jeschke Peter

  公开号：US20100240705A1

  公开（公告）日：2010-09-23

  The present application relates to novel substituted enaminocarbonyl compounds, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本申请涉及新型取代烯胺羰基化合物，其制备方法以及用于控制动物害虫，特别是节肢动物，尤其是昆虫的用途。
• SUBSTITUTED ENAMINOCARBONYL COMPOUNDS
  申请人：Jeschke Peter

  公开号：US20090247551A1

  公开（公告）日：2009-10-01

  The present invention relates to novel substituted enaminocarbonyl compounds, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本发明涉及新型取代烯胺羰基化合物，以及其制备方法和在控制动物害虫，特别是节肢动物，尤其是昆虫中的应用。
• N'-Cyano-N-Halogenalkylimidamide Derivatives
  申请人：Jeschke Peter

  公开号：US20100048646A1

  公开（公告）日：2010-02-25

  The present application relates to novel substituted N′-cyano-N-halogenalkylimidamide derivatives, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本申请涉及新型取代N'-氰基-N-卤代烷基咪唑酰胺衍生物，以及其制备方法和用于控制动物害虫，特别是节肢动物，尤其是昆虫的用途。
• BICYCLIC (THIO)CARBONYLAMIDINES
  申请人：BAYER INTELLECTUAL PROPERTY GMBH

  公开号：US20140113824A1

  公开（公告）日：2014-04-24

  Bicyclic (thio)carbonylamidines of the formula (I) in which Q, B, Y, R 1 and A are as defined in the description their preparation and their use for controlling plant pests and pests encountered in veterinary medicine.

  双环(thio)羰基脲类化合物的化学式为(I)，其中Q、B、Y、R1和A的定义详见说明书，本发明涉及其制备方法以及在控制植物害虫和兽医学中遇到的害虫中的应用。