2-(4-bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione | 61330-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(4-bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(4-bromo-2-fluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione；2-(4-bromo-2-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• CAS: 61330-04-9
• 化学式: C₁₄H₁₃BrFNO₂
• 分子量: 326.165
• InChiKey: NFCWCXBKBKSNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione 生成 Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-bromo-2-fluoro-phenyl)-amide] 2-pentylamide
  参考文献：
  名称：

  VAKABAYASI, OSAMU;ODA, XIRYUDZYU;NAOXARA, TEHTSUO;ISII, KADZUO

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴-2-氟苯胺 、 六氢苯酐 在 溶剂黄146 作用下， 反应 3.0h， 以96%的产率得到2-(4-bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis,In VitroProtoporphyrinogen Oxidase Inhibition, and Herbicidal Activity ofN-(Benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones andN-(Benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones

  摘要：

  Protoporphyrinogen oxidase (EC 1.3.3.4) is one of the most significant targets for a large family of herbicides. As part of our continuous efforts to search for novel protoporphyrinogen oxidase‐inhibiting herbicides, N‐(benzothiazol‐5‐yl)tetrahydroisoindole‐1,3‐dione was selected as a lead compound for structural optimization, leading to the syntheses of a series of novel N‐(benzothiazol‐5‐yl)hexahydro‐1H‐isoindole‐1,3‐diones (1a–o) and N‐(benzothiazol‐5‐yl)hexahydro‐1H‐isoindol‐1‐ones (2a–i). These newly prepared compounds were characterized by elemental analyses, 1H NMR, and ESI‐MS, and the structures of 1h and 2h were further confirmed by X‐ray diffraction analyses. The bioassays indicated that some compounds displayed comparable or higher protoporphyrinogen oxidase inhibition activities in comparison with the commercial control. Very promising, compound 2a, ethyl 2‐((6‐fluoro‐5‐(4,5,6,7‐tetrahydro‐1‐oxo‐1H‐isoindol‐2(3H)‐yl)benzo[d]thiazol‐2‐yl)‐sulfanyl)acetate, was recognized as the most potent candidate with Ki value of 0.0091 μm. Further greenhouse screening results demonstrated that some compounds exhibited good herbicidal activity against Chenopodium album at the dosage of 150 g/ha.

  DOI：

  10.1111/cbdd.12331

文献信息

• Substituted isoindoles
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04175948A1

  公开（公告）日：1979-11-27

  This invention relates to novel compounds of the formulae and their use as herbicides: ##STR1## wherein X is H, F, Cl, Br, CN, NO.sub.2 or OCH.sub.3 ; Y is H, F, or CH.sub.3 ; and Z is H, F, Cl, Br or OCH.sub.3 provided that (1) when Y is CH.sub.3, X is F, Cl, or Br; (2) when Z is 6-Cl or 6-Br, Y is F; and, (3) X, Y and Z may not all be H simultaneously.

  本发明涉及一种新的化合物及其作为除草剂的用途：其中X为H、F、Cl、Br、CN、NO2或OCH3；Y为H、F或CH3；Z为H、F、Cl、Br或OCH3，但要求（1）当Y为CH3时，X为F、Cl或Br；（2）当Z为6-Cl或6-Br时，Y为F；（3）X、Y和Z不能同时为H。
• Herbicidal 2-(substituted
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US03987057A1

  公开（公告）日：1976-10-19

  This invention relates to herbicidal 2-(substituted aryl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-diones. These compounds may be used for selective weed control for certain crops or for total vegetation control. In particular, the compounds may be utilized as rice herbicides and have the formula ##SPC1## Wherein X is Cl, Br or F, and Y is H or F, provided that when Y is F, X is F.

  本发明涉及除草剂2-(取代芳基)-3a,4,5,6,7,7a-六氢-1H-异吲哚-1,3(2H)-二酮。这些化合物可用于特定作物的选择性除草或全面植被控制。特别地，这些化合物可用作稻草田除草剂，其化学式为##SPC1## 其中X为Cl，Br或F，Y为H或F，但当Y为F时，X为F。
• VAKABAYASI, OSAMU;ODA, XIRYUDZYU;NAOXARA, TEHTSUO;ISII, KADZUO
  作者：VAKABAYASI, OSAMU、ODA, XIRYUDZYU、NAOXARA, TEHTSUO、ISII, KADZUO

  DOI：——

  日期：——
• US3987057A
  申请人：——

  公开号：US3987057A

  公开（公告）日：1976-10-19
• US4120693A
  申请人：——

  公开号：US4120693A

  公开（公告）日：1978-10-17