N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide | 84478-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide
• 英文别名: 2-(4-chloro-2-fluoro-5-prop-2-enoxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione
• CAS: 84478-49-9
• 化学式: C₁₇H₁₅ClFNO₃
• 分子量: 335.762
• InChiKey: XZMAVCUPEYDLSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 2.0h， 以72%的产率得到2-(4-chloro-2-fluoro-5-prop-2-enoxyphenyl)-3-hydroxy-4,5,6,7-tetrahydro-3H-isoindol-1-one
  参考文献：
  名称：

  Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors

  摘要：

  The characteristics of low application rates, good crop selectivity, low residue and environmental safety exhibited by Protoporphyrinogen oxidase (PPO, EC 1.3.3.4)-inhibiting herbicides have attracted a world-wide research interests. As continuation of our research work on the development of new PPO inhibitors, a series of mono-carbonyl analogues of cyclic imides, N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol- 2-ones, were designed and synthesized based on previously established DFT-QSAR results. The PPO inhibition activities of 29 newly synthesized compounds were tested and a predictive comparative molecular field analysis (CoMFA) model was established with the conventional correlation coefficient r(2) = 0.980 and the cross-validated coefficient q(2) = 0.518. According to the CoMFA model, the substituent effects on the PPO inhibition activity were explained reasonably. Further greenhouse assay showed that 2-(4-chloro-2-fluoro-5-propoxy-phenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one (C-6, k(i) = 0.095 mu M) and 2-(5-allyloxy-4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one (C-7, k(i) = 0.12 mu M) displayed excellent post-emergency herbicidal activity at the concentration of 150 g.ai/ha against seven tested weeds. Due to their high PPO inhibition effect and broad spectrum herbicidal activity, these two compounds have the potential for further study on crop selectivity and field trial. These results confirmed once again that only one of the carbonyl groups of cyclic imides is essential to the PPO inhibition activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.036
• 作为产物：
  描述：

  5-氨基-2-氯-4-氟苯酚 生成 N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide
  参考文献：
  名称：

  XASIMOTO, SYUNITI;JOSIDA, RE;MATSUMOTO, KEHJSI;KAMOSIMO, KATSUDZO

  摘要：

  DOI：

文献信息

• 2,3-dihydrobenzo[b]thiophenes
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04948418A1

  公开（公告）日：1990-08-14

  This invention pertains to novel heterocyclic 2,3-dihydrobenzofuran and chromane compounds, including stereoisomers, agriculturally suitable compositions containing them, and their use as broad spectrum herbicides.

  这项发明涉及新型杂环2,3-二氢苯并呋喃和色甘烷化合物，包括立体异构体，以及含有它们的适用于农业的组合物，以及它们作为广谱除草剂的用途。
• Chromane herbicides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05053071A1

  公开（公告）日：1991-10-01

  This invention pertains to novel heterocyclic 2,3-dihydrobenzofuran and chromane compounds, including stereoisomers, agriculturally suitable compositions containing them, and their use as broad spectrum herbicides.

  本发明涉及新型杂环2,3-二氢苯并呋喃和色甙化合物，包括立体异构体，适用于农业的含有它们的组合物，并将它们用作广谱除草剂的用途。
• Herbicidal substituted benzofurans and benzopyrans
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0271170A2

  公开（公告）日：1988-06-15

  Herbicidal N-(heterocyclyl)-substitued benzofurans and benzopyrans of the formulae: wherein the symbols have meanings described in the specification.

  除草剂 N-(杂环基)-取代的苯并呋喃和苯并吡喃，其式如下： 其中符号的含义见说明书。
• HETEROCYCLE-SUBSTITUTED BENZENE DERIVATIVE, PRODUCTION THEREOF, AND HERBICIDE CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0493606A1

  公开（公告）日：1992-07-08

  A heterocycle-substituted benzene derivative represented by general formula (I) wherein R represents C₃ to C₈ cycloalkyl, X represents halogen, and Z represents (Ia) or (Ib) provided that the cycloalkyl may be substituted with C₁ to C₆ alkyl. This compound is excellent in that it has a remarkably high herbicidal effect against weeds growing in both upland and lowland fields in a low dose, while it has a remarkably low phytotoxicity against main crops.

  一种杂环取代的苯衍生物，由通式(I)表示，其中 R 代表 C₃ 至 C₈ 环烷基，X 代表卤素，Z 代表(Ia)或(Ib)，但环烷基可被 C₁ 至 C₆ 烷基取代。这种化合物的优异之处在于，它对生长在高地和低地的杂草都有显著的高剂量除草效果，而对主要作物的植物毒性却很低。
• Benzene derivatives
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1006105A1

  公开（公告）日：2000-06-07

  Benzene derivatives useful as intermediates for the production of herbicides based on benzene derivatives substituted with a heterocyclic ring are disclosed.

  本发明公开了可用作生产除草剂中间体的苯衍生物，这些除草剂基于被杂环取代的苯衍生物。