2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one | 67115-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one
• 英文别名: 2-Methylcarbolinon；2-methyl-1,2-dihydro-9H-pyrido[3,4-b]indol-1-one；2-methyl-2,9-dihydro-β-carbolin-1-one；2-Methyl-2,9-dihydro-β-carbolin-1-on；2-Methyl-2,9-dihydro-beta-carbolin-1-one；2-methyl-9H-pyrido[3,4-b]indol-1-one
• CAS: 67115-07-5
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: YWBIWOGFSGRLOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 2-methyl-9H-β-carboline-1,3,4-trione
  参考文献：
  名称：

  Gliotoxin. V. The Structure of Certain Indole Derivatives Related to Gliotoxin^1,2

  摘要：

  DOI：

  10.1021/ja01219a023
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  Kermack; Perkin; Robinson, Journal of the Chemical Society, 1922, vol. 121, p. 1896

  摘要：

  DOI：

文献信息

• Triethyloxonium Tetrafluoroborate/1,2-Dimethoxyethane – a Versatile Substitute for Trimethyloxonium Tetrafluoroborate in O-Methylation Reactions
  作者：Andrea Ritter、Hermann Poschenrieder、Franz Bracher

  DOI：10.1515/znb-2009-0412

  日期：2009.4.1

  The triethyloxonium tetrafluoroborate/1,2-dimethoxyethane (TEO/DME) mixture is a versatile and cheap substitute for trimethyloxonium tetrafluoroborate in O-methylations of pyrrolin-2-ones, quinolones, acridones, and 1-oxo-β -carbolines. Undesired O-ethylation can be avoided by preincubation of triethyloxonium tetrafluoroborate and 1,2-dimethoxyethane for 1 h, prior to addition of the substrate. In the course of these investigations it was found that the structures assigned to the alkaloids taraxacine A and B are erroneous.

  三乙氧基四氟硼酸盐/二甲氧基乙烷（TEO/DME）混合物是一种多功能且便宜的三甲氧基四氟硼酸盐在吡咯烷-2-酮，喹啉酮，乙酰喹啉和1-氧代-β-咔啉的O-甲基化反应中的替代品。通过在加入底物之前将三乙氧基四氟硼酸盐和二甲氧基乙烷预先孵育1小时，可以避免不必要的O-乙基化。在这些研究中发现，分配给蒲公英碱A和B的结构是错误的。
• Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels–Alder Cycloaddition**
  作者：Wei Cao、Yingchao Dou、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1002/anie.202209135

  日期：2022.9.19

  A late stage bioinspired intramolecular Diels–Alder cycloaddition of the indolopyridone of ophiorrhiside E was deployed to access the spirocyclic azabicyclic[2.2.2]octanone ring system of ophiorrhiside A and achieve its total synthesis. The indolopyridone of ophiorrhiside E was synthesized by the cyclodehydration of ophiorrhine G which was formed by the acylation of N-methyl indolylacetamide by a secologanin

  采用后期仿生分子内 Diels-Alder 环加成法对蛇草苷 E 的吲哚并吡啶酮进行环加成，以获取蛇草苷 A 的螺环氮杂双环[2.2.2]辛酮环系统并实现其全合成。蛇草苷E的吲哚并吡啶酮是通过蛇草碱G的环化脱水合成的，蛇草碱G是由N-甲基吲哚基乙酰胺被赛洛加宁衍生物酰化形成的。
• Pd/Cu Cocatalyzed Oxidative Tandem C–H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
  作者：Hui Han、Shang-Dong Yang、Ji-Bao Xia

  DOI：10.1021/acs.joc.8b03266

  日期：2019.3.15

  The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.
• Gliotoxin. VII. Synthesis of Pyrazinoindolones and Pyridindolones¹
  作者：John R. Johnson、Aubrey A. Larsen、Ann D. Holley、Koert Gerzon

  DOI：10.1021/ja01202a034

  日期：1947.10
• Gliotoxin. V. The Structure of Certain Indole Derivatives Related to Gliotoxin^1,2
  作者：John R. Johnson、Richard B. Hasbrouck、James D. Dutcher、William F. Bruce

  DOI：10.1021/ja01219a023

  日期：1945.3