[6-溴-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸 | 289503-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [6-溴-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸
• 英文名称: N-tosyl-6-bromo-3-indolylboronic acid
• 英文别名: N-tosyl-6-bromoindol-3-ylboronic acid；Boronic acid, [6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-；[6-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]boronic acid
• CAS: 289503-26-0
• 化学式: C₁₅H₁₃BBrNO₄S
• 分子量: 394.054
• InChiKey: CAVKNPOIZLDLLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  621.7±65.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  6-溴-1-甲苯磺酰-1H-吲哚	N-tosyl-6-bromoindole	189265-99-4	C15H12BrNO2S	350.236
  ——	N-tosyl-3,6-dibromoindole	289503-25-9	C15H11Br2NO2S	429.132

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-amino-4-(N-tosyl-6'-bromo-3'-indolyl)pyrimidine	289503-27-1	C19H15BrN4O2S	443.324
  ——	6-Bromo-3-[6-[6-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-4-(trifluoromethyl)pyridin-2-yl]-1-(4-methylphenyl)sulfonylindole	——	C36H24Br2F3N3O4S2	843.539
  ——	5-bromo-3-methoxy-2-(N-tosyl-6-bromoindol-3-yl)pyrazine	476623-17-3	C20H15Br2N3O3S	537.231
  ——	6-Bromo-3-{3-methoxy-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-3-yl]-pyrazin-2-yl}-1-(toluene-4-sulfonyl)-1H-indole	1026440-93-6	C34H35BrN4O4SSi	703.732

反应信息

• 作为反应物：
  描述：

  [6-溴-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸 在 四(三苯基膦)钯 sodium hydroxide 、 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.5h， 生成 Meridianin D
  参考文献：
  名称：

  Synthesis of Indolylpyrimidines via Cross-Coupling of Indolylboronic Acid with Chloropyrimidines: Facile Synthesis of Meridianin D

  摘要：

  Palladium catalyzed cross-coupling reaction of 3-indolylboronic acid with 2,4-dichloropyrimidines proceeded regioselectively to yield indolyl-or bis(indolyl)pyrimidines in high yield, depending on the projection of 3-indolylboronic acid. The marine indole alkaloid meridianin D and an analogue were synthesised via the palladium catalyzed cross-coupling reaction as a key step.

  DOI：

  10.3987/com-00-8890
• 作为产物：
  描述：

  6-溴-1-甲苯磺酰-1H-吲哚 在 高氯酸 、 mercury(II) diacetate 、 溶剂黄146 、 硼烷四氢呋喃络合物 、 水 作用下， 反应 25.0h， 生成 [6-溴-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸
  参考文献：
  名称：

  Dragmacidin D的首次全合成

  摘要：

  已经实现了具有生物学意义的双吲哚生物碱 Dragmacidin D (5) 的首次全合成。热和电子调制为一系列钯催化的 Suzuki 交叉偶联反应提供了关键，这些反应提供了含有胍和氨基咪唑的复杂药物的核心结构。按照这个关键的顺序，一系列精心控制的最终事件被开发出来，导致天然产品的完成。

  DOI：

  10.1021/ja027822b

文献信息

• The formal total synthesis of dragmacidin B, trans-dragmacidin C, and cis- and trans-dihydrohamacanthins A
  作者：Neil K. Garg、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2005.02.054

  日期：2005.4

  A facile formal total synthesis of dragmacidin B, trans-dragmacidin C, and cis- and trans-dihydrohamacanthins A is presented. Our approach to these bis(indole) alkaloids involves a one-pot, four-step cross-coupling/deprotection sequence where complete halogen selectivity is observed. A related approach to access the dihydrohamacanthins is also described.

  提出了一种简单的正式全合成的drammacidin B，trans -dragmacidin C和cis-和trans -dihydrohamacanthinsA 。我们对这些双（吲哚）生物碱的方法涉及一锅四步交叉偶联/去保护序列，其中观察到完全的卤素选择性。还描述了访问二氢金刚烷类的相关方法。
• Preparing Functional Bis(indole) Pyrazine by Stepwise Cross-coupling Reactions:  An Efficient Method to Construct the Skeleton of Dragmacidin D
  作者：Cai-Guang Yang、Gang Liu、Biao Jiang

  DOI：10.1021/jo026450m

  日期：2002.12.1

  properly substituted bis(indole) pyrazine, the skeleton of a marine alkaloid dragmacidin D, has been developed. The key steps involved the regioselective introduction of two indole units, using the palladium(0)-catalyzed Suzuki and the Stille cross-coupling reactions sequentially.

  已经开发出一种选择性构建适当取代的双（吲哚）吡嗪的直接方法，该双（吲哚）吡嗪是海洋生物碱德拉莫达汀D的骨架。关键步骤涉及依次使用钯（0）催化的Suzuki和Stille交叉偶联反应，对两个吲哚单元进行区域选择性引入。
• 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.
• 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.