2-(1-naphtghyl)-1,3,4(2H)-isoquinolinetrione | 240115-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(1-naphtghyl)-1,3,4(2H)-isoquinolinetrione
• 英文别名: 2-[1]naphthyl-isoquinoline-1,3,4-trione；2-[1]Naphthyl-isochinolin-1,3,4-trion；2-Naphthalen-1-ylisoquinoline-1,3,4-trione；2-naphthalen-1-ylisoquinoline-1,3,4-trione
• CAS: 240115-30-4
• 化学式: C₁₉H₁₁NO₃
• 分子量: 301.301
• InChiKey: QNTNTMBXVIDPRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-naphtghyl)-1,3,4(2H)-isoquinolinetrione 、 苯肼 在 sodium acetate 、 溶剂黄146 作用下， 生成 2-[1]naphthyl-isoquinoline-1,3,4-trione-4-phenylhydrazone
  参考文献：
  名称：

  Meyer; Vittenet, Annales de Chimie (Cachan, France), 1932, vol. <10>17, p. 271,388,390

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[1]naphthyl-4H-isoquinoline-1,3-dione 生成 2-(1-naphtghyl)-1,3,4(2H)-isoquinolinetrione
  参考文献：
  名称：

  Herbicidal activity of 2-substituted 1,3,4-(2H)-isoquinolinetriones

  摘要：

  A series of 2-substituted 1,3,4-isoquinolinetriones (B) 1-15, precursors of the phthalamic acids and of the 1,3-dihydro-1-hydroxy-3-oxo-1-isobenzofurancarboxamides (F), possessing root antigravitropic activities, were prepared and evaluated for herbicidal activity on weeds and crops. Among the compounds examined, several derivatives were very active against weeds, in many cases more active than the commercially available herbicides used as the reference standards. Phytotoxicities on crops, selectivity and persistence of herbicidal effect were observed. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00037-3

文献信息

• On the reactions of 1,3-isoquinolinediones with singlet oxygen
  作者：Ke-Qing Ling、Jia-Hai Ye、Xian-Yang Chen、De-Jian Ma、Jian-Hua Xu

  DOI：10.1016/s0040-4020(99)00502-5

  日期：1999.7

  view of these observations, an unusual [4+2] cycloaddition of the electron-rich enol 21 with singlet oxygen is proposed to be responsible for the formation of products 7 and 16, while products 6, 14 and 15 arise from both the [4+2] cycloaddition and the usual Schenck ene reaction pathways. This special diene reactivity of the isoquinolinone system towards singlet oxygen is further interpreted by frontier

  1，3-异喹啉二酮5和4-烷基化的1，3-异喹啉二酮13与单线态氧的反应完全被烯醇化控制，并且在吡啶作为碱和氢键受体的存在下在苯中平稳地进行。该产品是三酮类6和benzoisofuranones 7为5，和氢过氧化物14，氢氧化物15和benzoisofuranones 16为13。发现6的水解提供了异吲哚酮8而不是产物7，而氢过氧化物14a的碱性裂解不仅产生16a，还产生异吲哚酮19a。鉴于这些观察结果，提出了富电子的烯醇21与单线态氧的不寻常的[4 + 2]环加成反应，导致产物7和16的形成，而产物6、14和15则由[ [4 + 2]环加成反应和通常的Schenck烯反应途径。前沿分子轨道（FMO）相互作用的考虑进一步解释了异喹啉酮系统对单线态氧的这种特殊的二烯反应性。
• 一种异喹啉-1,3,4-三酮衍生物及其制备方法
  申请人：苏州大学

  公开号：CN106083718B

  公开（公告）日：2018-11-02

  本发明公开了一种异喹啉‑1,3,4‑三酮衍生物及其制备方法，所述方法步骤包括：以3‑氨基‑4‑氰基‑2‑取代异喹啉‑1‑酮衍生物为底物，以铜盐为催化剂，在有机溶剂中，与过氧化叔丁醇水溶液在60‑80℃下反应，制得异喹啉‑1,3,4‑三酮衍生物。本发明的方法可以高收率的得到多个异喹啉‑1,3,4‑三酮衍生物；反应条件温和、操作和后处理过程简单，适合于规模化生产。
• Meyer; Vittenet, Annales de Chimie (Cachan, France), 1932, vol. <10>17, p. 271,383,385
  作者：Meyer、Vittenet

  DOI：——

  日期：——
• Meyer; Vittenet, Annales de Chimie (Cachan, France), 1932, vol. <10>17, p. 271,391,392
  作者：Meyer、Vittenet

  DOI：——

  日期：——
• Herbicidal activity of 2-substituted 1,3,4-(2H)-isoquinolinetriones
  作者：Marco Mazza、Tiziana Modena

  DOI：10.1016/s0014-827x(99)00037-3

  日期：1999.6

  A series of 2-substituted 1,3,4-isoquinolinetriones (B) 1-15, precursors of the phthalamic acids and of the 1,3-dihydro-1-hydroxy-3-oxo-1-isobenzofurancarboxamides (F), possessing root antigravitropic activities, were prepared and evaluated for herbicidal activity on weeds and crops. Among the compounds examined, several derivatives were very active against weeds, in many cases more active than the commercially available herbicides used as the reference standards. Phytotoxicities on crops, selectivity and persistence of herbicidal effect were observed. (C) 1999 Elsevier Science S.A. All rights reserved.