2-Butoxy-6-chloro-3-nitropyridine | 1094848-35-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-Butoxy-6-chloro-3-nitropyridine
• CAS: 1094848-35-7
• 化学式: C₉H₁₁ClN₂O₃
• 分子量: 230.651
• InChiKey: NFCLYOLZFOVQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基}-1-丙醇 、 2-Butoxy-6-chloro-3-nitropyridine 以 四氢呋喃 为溶剂， 生成 2-butoxy-6-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-3-nitropyridine
  参考文献：
  名称：

  Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers

  摘要：

  Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.

  DOI：

  10.1021/acs.jafc.5b02279
• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 、 正丁醇 在 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 2-Butoxy-6-chloro-3-nitropyridine
  参考文献：
  名称：

  Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers

  摘要：

  Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.

  DOI：

  10.1021/acs.jafc.5b02279

文献信息

• Microwave-Assisted Silver(I)-Mediated Selective O-Alkylation of Aromatic Imidate Systems
  作者：Erik Van der Eycken、Brajendra Singh、Claudia Cavalluzzo、Marc De Maeyer、Zeger Debyser、Virinder Parmar

  DOI：10.1055/s-0029-1216878

  日期：——

  A novel microwave-assisted protocol has been developed for the selective O-alkylation of aromatic imidate systems with various halides under microwave irradiation using silver carbonate as the base. Products were obtained in short reaction time and in excellent yields.

  一种新颖的微波辅助协议已被开发，用于在微波辐照下使用碳酸银作为碱，对芳香咪唑酰胺体系进行选择性O-烷基化，反应时间短且产率优异。
• TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS
  申请人：Biswas Kaustav

  公开号：US20130157996A1

  公开（公告）日：2013-06-20

  Compounds of Formula I are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物可用作TRPM8的拮抗剂。这些化合物在治疗许多TRPM8介导的疾病和病症方面非常有用，并可用于制备用于治疗此类疾病和病症的药物和制剂。此类疾病的示例包括但不限于偏头痛和神经病性疼痛。公式I的化合物具有以下结构：其中变量的定义在此提供。
• US8710043B2
  申请人：——

  公开号：US8710043B2

  公开（公告）日：2014-04-29
• US9096527B2
  申请人：——

  公开号：US9096527B2

  公开（公告）日：2015-08-04
• [EN] TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS<br/>[FR] ANTAGONISTES DE TRPM8 ET LEUR UTILISATION DANS DES TRAITEMENTS
  申请人：AMGEN INC

  公开号：WO2012177893A2

  公开（公告）日：2012-12-27

  Compounds of Formula (I) are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula (I) have a structure where the definitions of the variables are provided herein.