[1-(4-Methylphenyl)sulfonyl-5-phenylmethoxyindol-3-yl]boronic acid | 339540-16-8

• 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: [1-(4-Methylphenyl)sulfonyl-5-phenylmethoxyindol-3-yl]boronic acid
• 英文别名: [1-(4-methylphenyl)sulfonyl-5-phenylmethoxyindol-3-yl]boronic acid
• CAS: 339540-16-8
• 化学式: C₂₂H₂₀BNO₅S
• 分子量: 421.281
• InChiKey: BFLQCDZAJMXGKV-UHFFFAOYSA-N

物化性质

• 沸点：
  679.9±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-4-三氟甲基吡啶 、 [1-(4-Methylphenyl)sulfonyl-5-phenylmethoxyindol-3-yl]boronic acid 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 以87%的产率得到1-(4-Methylphenyl)sulfonyl-5-phenylmethoxy-3-[4-(trifluoromethyl)pyridin-2-yl]indole
  参考文献：
  名称：

  Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents

  摘要：

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00070-0
• 作为产物：
  描述：

  5-(benzyloxy)-1-tosyl-1H-indole 在 mercury(II) diacetate 、 二甲基硫 、 硼烷 、 水 作用下， 以 溶剂黄146 、 四氢呋喃 为溶剂， 反应 1.0h， 生成 [1-(4-Methylphenyl)sulfonyl-5-phenylmethoxyindol-3-yl]boronic acid
  参考文献：
  名称：

  Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents

  摘要：

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00070-0

文献信息

• A highly stereoselective synthesis of indolyl N-substituted glycines
  作者：Biao Jiang、Cai-Guang Yang、Xiao-Hui Gu

  DOI：10.1016/s0040-4039(01)00229-5

  日期：2001.3

  Optically active alpha -indolyl N-substituted glycines were synthesized by reaction of an indolyl boronic acid with glyoxylic acid using chiral methylbenzylamine as the chiral auxiliary with high diastereoselectivity. The absolute configuration of the product was determined by a single-crystal X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and antitumor evaluation of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines
  作者：Biao Jiang、Xen-Nan Xiong、Cai-Guang Yang

  DOI：10.1016/s0960-894x(00)00704-6

  日期：2001.2

  A series of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines was designed and synthesized as potential antitumor agents. They were evaluated for preliminary cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxyl-indolyl)] pyridine was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents
  作者：Wen-Nan Xiong、Cai-Guang Yang、Biao Jiang

  DOI：10.1016/s0968-0896(01)00070-0

  日期：2001.7

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.