6-benzyl-11-hydroxy-11H-indeno[1,2-c]isoquinolin-5-one | 1018679-04-3

• 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: 6-benzyl-11-hydroxy-11H-indeno[1,2-c]isoquinolin-5-one
• CAS: 1018679-04-3
• 化学式: C₂₃H₁₇NO₂
• 分子量: 339.393
• InChiKey: ADLKKNYKCKAUGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-benzyl-11-hydroxy-11H-indeno[1,2-c]isoquinolin-5-one 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到6-benzyl-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
  参考文献：
  名称：

  Photochemically Induced Synthesis of the Topoisomerase I Inhibitors Indeno[1,2-c]isoquinoline-5,11-diones

  摘要：

  A convenient synthesis of indeno[1,2-c]isoquinoline-5,11-diones has been achieved using combinational photochemical and carbocationic cyclization tactics. The synthetic route involved first the construction of adequately functionalized N-styryl benzamides via Suzuki-Miyaura cross-coupling reaction with enol phosphate combined with a six-p-electron photocyclization process. The assembling of the title compounds was readily ensured through sequential carbocationic annulation reaction and ultimate oxidation of a latent hydroxy functionality.

  DOI：

  10.1055/s-0031-1290751
• 作为产物：
  描述：

  N-苄基-2-甲氧基苯甲酰胺 在 盐酸 、 重铬酸吡啶 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 6-benzyl-11-hydroxy-11H-indeno[1,2-c]isoquinolin-5-one
  参考文献：
  名称：

  Photochemically Induced Synthesis of the Topoisomerase I Inhibitors Indeno[1,2-c]isoquinoline-5,11-diones

  摘要：

  A convenient synthesis of indeno[1,2-c]isoquinoline-5,11-diones has been achieved using combinational photochemical and carbocationic cyclization tactics. The synthetic route involved first the construction of adequately functionalized N-styryl benzamides via Suzuki-Miyaura cross-coupling reaction with enol phosphate combined with a six-p-electron photocyclization process. The assembling of the title compounds was readily ensured through sequential carbocationic annulation reaction and ultimate oxidation of a latent hydroxy functionality.

  DOI：

  10.1055/s-0031-1290751

文献信息

• METHOD FOR PREPARING INDENOISOQUINOLINE DERIVATIVES
  申请人：National Taiwan Normal University

  公开号：EP3480187A1

  公开（公告）日：2019-05-08

  A method for preparing indenoisoquinoline derivatives represented by the following formula (I) is disclosed, which comprises the following steps: (A) providing a first reactant represented by the following formula (II) and a second reactant represented by the following formula (III): and (B) reacting the first reactant represented by the formula (II) and the second reactant represented by the formula (III) in a solvent and selectively adding R2NH2 therein, to obtain the indenoisoquinoline derivatives represented by the formula (I), wherein, R1, R2, R3, A, X, Y, Z, m and n are defined in the specification.

  本发明公开了一种制备下式（I）所代表的茚并异喹啉衍生物的方法，该方法包括以下步骤： (A) 提供下式（II）代表的第一反应物和下式（III）代表的第二反应物： 和 (B) 将式（II）代表的第一反应物和式（III）代表的第二反应物在溶剂中反应并选择性地加入 R2NH2，得到式（I）代表的茚并异喹啉衍生物，其中 R1、R2、R3、A、X、Y、Z、m 和 n 在说明书中定义。
• Photochemically Induced Synthesis of the Topoisomerase I Inhibitors Indeno[1,2-c]isoquinoline-5,11-diones
  作者：Axel Couture、Mélanie Dubois、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-0031-1290751

  日期：2012.4

  A convenient synthesis of indeno[1,2-c]isoquinoline-5,11-diones has been achieved using combinational photochemical and carbocationic cyclization tactics. The synthetic route involved first the construction of adequately functionalized N-styryl benzamides via Suzuki-Miyaura cross-coupling reaction with enol phosphate combined with a six-p-electron photocyclization process. The assembling of the title compounds was readily ensured through sequential carbocationic annulation reaction and ultimate oxidation of a latent hydroxy functionality.