6-Chloro-2-[(2-methylpropan-2-yl)oxy]-3-nitropyridine | 1094235-39-8

• 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: 6-Chloro-2-[(2-methylpropan-2-yl)oxy]-3-nitropyridine
• CAS: 1094235-39-8
• 化学式: C₉H₁₁ClN₂O₃
• 分子量: 230.651
• InChiKey: WQPGKDWASPGVLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 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 、 6-Chloro-2-[(2-methylpropan-2-yl)oxy]-3-nitropyridine 以 四氢呋喃 为溶剂， 生成 2-(tert-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 、 叔丁醇 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以95%的产率得到6-Chloro-2-[(2-methylpropan-2-yl)oxy]-3-nitropyridine
  参考文献：
  名称：

  邻-选择性的亲核芳族取代（S Ñ AR）与碱金属醇盐的3-取代的，2,6- dichloropyridines反应

  摘要：

  3-取代的2,6-二氯吡啶已被广泛用于多种生物学靶标的小分子抑制剂的合成中。因此，氯的区域选择性置换是令人关注的。通过进行广泛的溶剂研究，我们发现低氢键碱性的非极性非质子溶剂有利于用碱金属醇盐将邻氯取代为3-取代基。我们提供令人信服的证据，表明碱金属抗衡离子与3-取代基（硝基，酯，酰胺）的配位是邻位选择性产生环状六元过渡态的起源。优秀的邻钠抗衡离子可实现仲和叔醇盐的选择性（⩾98：2），而反应性较高的伯醇盐则需要更硬，更路易斯的酸性锂抗衡离子。

  DOI：

  10.1016/j.tetlet.2011.06.007

文献信息

• Ortho-selectivity in the nucleophilic aromatic substitution (SNAr) reactions of 3-substituted, 2,6-dichloropyridines with alkali metal alkoxides
  作者：Jeremy L. Yap、Kellie Hom、Steven Fletcher

  DOI：10.1016/j.tetlet.2011.06.007

  日期：2011.8

  basicities favour substitution of the chlorine ortho to the 3-substituent by alkali metal alkoxides. We present convincing evidence that coordination of the alkali metal counter-ion to the 3-substituent (nitro, ester, amide) is the origin of the ortho-selectivity to give a cyclic, six-membered transition state. Excellent ortho-selectivities (⩾98:2) for secondary and tertiary alkoxides were realized with

  3-取代的2,6-二氯吡啶已被广泛用于多种生物学靶标的小分子抑制剂的合成中。因此，氯的区域选择性置换是令人关注的。通过进行广泛的溶剂研究，我们发现低氢键碱性的非极性非质子溶剂有利于用碱金属醇盐将邻氯取代为3-取代基。我们提供令人信服的证据，表明碱金属抗衡离子与3-取代基（硝基，酯，酰胺）的配位是邻位选择性产生环状六元过渡态的起源。优秀的邻钠抗衡离子可实现仲和叔醇盐的选择性（⩾98：2），而反应性较高的伯醇盐则需要更硬，更路易斯的酸性锂抗衡离子。
• Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers
  作者：Aiping Liu、Wanqi Yu、Minhua Liu、Jianjun Bai、Weidong Liu、Xingping Liu、Hui Pei、Li Hu、Mingzhi Huang、Xiaoguang Wang

  DOI：10.1021/acs.jafc.5b02279

  日期：2015.9.2

  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.