3-(tert-butyldiphenylsilyloxy)-4-methylaniline | 1197392-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(tert-butyldiphenylsilyloxy)-4-methylaniline
• 英文别名: 3-[Tert-butyl(diphenyl)silyl]oxy-4-methylaniline
• CAS: 1197392-20-3
• 化学式: C₂₃H₂₇NOSi
• 分子量: 361.559
• InChiKey: NRDLRYFZOFLEOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldiphenylsilyloxy)-4-methylaniline 在 titanium(IV) isopropylate 、 四丁基氟化铵 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 72.0h， 生成 O-methylmurrayamine A
  参考文献：
  名称：

  Total synthesis and neuroprotective effect of O-methylmurrayamine A and 7-methoxymurrayacine

  摘要：

  O-Methylmurrayamine A (7) and 7-methoxymurrayacine (8) are natural products isolated from Murraya koenigii and Murraya siamensis, respectively. In this paper, we report the synthesis of 7 and 8 which are featured in the key step of cyclization to form carbazole intermediate 5 with mild conditions. The structures were confirmed by H-1 NMR, C-13 NMR, and HR-ESI-MS. In addition, compounds 7 and 8 were tested for their neuroprotective effects against H2O2 -induced PC12 cell damage. The results showed that compounds 7 and 8 have neuroprotective effect.

  DOI：

  10.1080/10286020.2017.1327952
• 作为产物：
  描述：

  3-tert-butyldiphenylsilyloxy-4-methylnitrobenzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 24.0h， 生成 3-(tert-butyldiphenylsilyloxy)-4-methylaniline
  参考文献：
  名称：

  有机合成中的过渡金属，第 91 部分：¹ 钯催化制备 2,6-双氧合咔唑生物碱的方法 - 植物抗毒素 Carbalexin C 的首次全合成

  摘要：

  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。

  DOI：

  10.1055/s-0029-1217810

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.
• Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo
  作者：Yingda Zang、Xiuyun Song、Chuangjun Li、Jie Ma、Shifeng Chu、Dandan Liu、Qian Ren、Yan Li、Naihong Chen、Dongming Zhang

  DOI：10.1016/j.ejmech.2017.11.084

  日期：2018.1

  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.
• Total synthesis and neuroprotective effect of O-methylmurrayamine A and 7-methoxymurrayacine
  作者：Ying-Da Zang、Chuang-Jun Li、Xiu-Yun Song、Jie Ma、Jing-Zhi Yang、Nai-Hong Chen、Dong-Ming Zhang

  DOI：10.1080/10286020.2017.1327952

  日期：2017.6.3

  O-Methylmurrayamine A (7) and 7-methoxymurrayacine (8) are natural products isolated from Murraya koenigii and Murraya siamensis, respectively. In this paper, we report the synthesis of 7 and 8 which are featured in the key step of cyclization to form carbazole intermediate 5 with mild conditions. The structures were confirmed by H-1 NMR, C-13 NMR, and HR-ESI-MS. In addition, compounds 7 and 8 were tested for their neuroprotective effects against H2O2 -induced PC12 cell damage. The results showed that compounds 7 and 8 have neuroprotective effect.