8,9,10-trimethoxy-11H-indolo[1,2-b]isoquinoline-6-one | 154885-41-3

• 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: 8,9,10-trimethoxy-11H-indolo[1,2-b]isoquinoline-6-one
• 英文别名: 5-oxo-1,2,3-trimethoxyisoquinolono<2,3-a>indole；Indolo[1,2-b]isoquinolin-6(11H)-one, 8,9,10-trimethoxy-；8,9,10-trimethoxy-11H-indolo[1,2-b]isoquinolin-6-one
• CAS: 154885-41-3
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: OTQPFDXXJOKAHK-UHFFFAOYSA-N

物化性质

• 沸点：
  471.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8,9,10-trimethoxy-11H-indolo[1,2-b]isoquinoline-6-one 在 PPA 作用下， 反应 2.0h， 生成 1,2,3-trimethoxy-5,11-dihydroindolo[1,2-b]isoquinoline-5,11-dione
  参考文献：
  名称：

  1,2,3-Trimethoxy-5,11-dihydroindolo[1,2-b]isoquinoline-5,11-dione

  摘要：

  The title compound, C15H19NO5, crystallizes in the monoclinic space group P2(1)/c with four molecules in the asymmetric unit, which differ from each other in the orientation of their methoxy groups. Of the three methoxy groups in each molecule, one lies close to the plane of the molecule and the other two have an out-of-plane conformation where they point in opposite directions. In the crystal structure, four different types of pi-stacks are observed and the molecules pack in two different types of stacking sheets, with alternating molecules A and B in one ribbon and alternating molecules C and D in the other. The supramolecular structure is supported by C - H center dot center dot center dot O and pi-pi interactions.

  DOI：

  10.1107/s0108270105035158
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 Raney nickel (W-2) 、 sodium hydride 、 copper dichloride 、 palladium dichloride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 乙腈 为溶剂， 反应 41.0h， 生成 8,9,10-trimethoxy-11H-indolo[1,2-b]isoquinoline-6-one
  参考文献：
  名称：

  Synthesis of Benzocarbazoloquinones via Oxidative Cyclization

  摘要：

  1-苯磺酰基-2-溴甲基-5-甲氧基吲哚-3-羧酸乙酯（2）和 2-甲基-3-苯硫基吲哚（5）分别转化为苯并咔唑醌类化合物 4 和 10，其中涉及在使用多磷酸时空气的氧化环化作用。

  DOI：

  10.1055/s-1994-25456

文献信息

• Synthesis of Benzocarbazoloquinones via Oxidative Cyclization
  作者：W. G. Rajeswaran、P. C. Srinivasan

  DOI：10.1055/s-1994-25456

  日期：——

  Ethyl 1-benzenesulfonyl-2-bromomethyl-5-methoxyindole-3-carboxylate (2) and 2-methyl-3-phenylthioindole (5) have been converted into benzcarbazoloquinones 4 and 10, respectively, involving an oxidative cyclization by air during the application of polyphosphoric acid.

  1-苯磺酰基-2-溴甲基-5-甲氧基吲哚-3-羧酸乙酯（2）和 2-甲基-3-苯硫基吲哚（5）分别转化为苯并咔唑醌类化合物 4 和 10，其中涉及在使用多磷酸时空气的氧化环化作用。
• 1,2,3-Trimethoxy-5,11-dihydroindolo[1,2-<i>b</i>]isoquinoline-5,11-dione
  作者：M. Yogavel、D. Velmurugan、W. G. Rajeswaran、P. C. Srinivasan、H.-K. Fun

  DOI：10.1107/s0108270105035158

  日期：2005.12.15

  The title compound, C15H19NO5, crystallizes in the monoclinic space group P2(1)/c with four molecules in the asymmetric unit, which differ from each other in the orientation of their methoxy groups. Of the three methoxy groups in each molecule, one lies close to the plane of the molecule and the other two have an out-of-plane conformation where they point in opposite directions. In the crystal structure, four different types of pi-stacks are observed and the molecules pack in two different types of stacking sheets, with alternating molecules A and B in one ribbon and alternating molecules C and D in the other. The supramolecular structure is supported by C - H center dot center dot center dot O and pi-pi interactions.