2-(tert-butyldiphenylsilyloxy)-6-methoxy-3-methyl-9H-carbazole | 1197392-22-5

• 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-(tert-butyldiphenylsilyloxy)-6-methoxy-3-methyl-9H-carbazole
• 英文别名: O-tert-butyldiphenylsulylcarbalexin C；tert-butyl-[(6-methoxy-3-methyl-9H-carbazol-2-yl)oxy]-diphenylsilane
• CAS: 1197392-22-5
• 化学式: C₃₀H₃₁NO₂Si
• 分子量: 465.667
• InChiKey: AQZVUQXKJQWBIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldiphenylsilyloxy)-6-methoxy-3-methyl-9H-carbazole 在 titanium(IV) isopropylate 、 四丁基氟化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 46.5h， 生成 claulansine F
  参考文献：
  名称：

  Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

  摘要：

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.084
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)-4-methylaniline 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 2-(tert-butyldiphenylsilyloxy)-6-methoxy-3-methyl-9H-carbazole
  参考文献：
  名称：

  Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

  摘要：

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.084

文献信息

• Transition Metals in Organic Synthesis, Part 91:¹ Palladium-Catalyzed Approach to 2,6-Dioxygenated Carbazole Alkaloids - First Total Synthesis of the Phytoalexin Carbalexin C
  作者：Hans-Joachim Knölker、Marika Schmidt

  DOI：10.1055/s-0029-1217810

  日期：2009.9

  The palladium(0)-catalyzed C-N bond formation and palladium(II)-catalyzed oxidative cyclization provide an efficient route to a series of 2,6-dioxygenated carbazole alkaloids including the first total synthesis of the phytoalexin carbalexin C.

  钯 (0) 催化的 CN 键形成和钯 (II) 催化的氧化环化为一系列 2,6-二氧化咔唑生物碱提供了有效途径，包括植物抗毒素卡巴莱辛 C 的首次全合成。
• Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine
  作者：Hans-Joachim Knölker、Christian Schuster、Marika Rönnefahrt、Konstanze Julich-Gruner、Anne Jäger、Arndt Schmidt

  DOI：10.1055/s-0035-1560359

  日期：——

  Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.