(4-bromophenyl)(1H-indol-5-yl)methanone | 881006-11-7

• 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: (4-bromophenyl)(1H-indol-5-yl)methanone
• 英文别名: Methanone,(4-bromophenyl)-1h-indol-5-yl-；(4-bromophenyl)-(1H-indol-5-yl)methanone
• CAS: 881006-11-7
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: CLKLXEZSEOIXNO-UHFFFAOYSA-N

物化性质

• 沸点：
  468.6±20.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)(1H-indol-5-yl)methanone 在 sodium tetrahydroborate 、 四(三苯基膦)钯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 生成 4-[Hydroxy-(1H-indol-5-yl)-methyl]-benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099
• 作为产物：
  描述：

  1-benzenesulfonyl-2,3-dihydro-1H-indole 在 manganese(IV) oxide 、 三氯化铝 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.08h， 生成 (4-bromophenyl)(1H-indol-5-yl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099

文献信息

• A Simple, Efficient, and Recyclable Phosphine-Free Catalytic System for Carbonylative Suzuki Coupling Reaction of Aryl and Heteroaryl Iodides
  作者：Bhalchandra Bhanage、Ziyauddin Qureshi、Krishna Deshmukh、Pawan Tambade

  DOI：10.1055/s-0030-1258349

  日期：2011.1

  The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole

  描述了使用聚合物负载的钯-N-杂环卡宾配合物（PS-Pd-NHC）作为有效的多相可循环催化剂，芳基硼酸与芳基和杂芳基碘化物进行羰基化Suzuki偶联反应。发现开发的催化体系对于芳基，杂芳基和双环杂芳基碘化物（5-碘吲哚和3-碘喹啉）与各种芳基硼酸衍生物的羰基化偶联反应有效，从而提供了所需产品的良好或优异的收率。由于催化剂的易于处理和简单的后处理程序，并且对环境有益且催化剂有效地可回收，该方案是有利的。 联芳基酮-硼-多相催化-钯-铃木羰基化
• Pd/C: An Efficient, Heterogeneous and Reusable Catalyst for Phosphane-Free Carbonylative Suzuki Coupling Reactions of Aryl and Heteroaryl Iodides
  作者：Mayur V. Khedkar、Pawan J. Tambade、Ziyauddin S. Qureshi、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201001134

  日期：2010.12

  The carbonylative Suzuki coupling reaction of aryl boronic acid with different aryl and heteroaryl iodides was carried out to synthesize various unsymmetrical biaryl ketones by using Pd/C as an efficient, heterogeneous and reusable catalyst. The catalyst exhibits remarkable activity, and its reusability was tested up to four consecutive cycles. The reaction is applicable for various aryl and heteroaryl

  以Pd/C为高效、多相和可重复使用的催化剂，芳基硼酸与不同芳基和杂芳基碘化物发生羰基化Suzuki偶联反应合成各种不对称联芳基酮。该催化剂表现出显着的活性，其可重复使用性经过连续四个循环的测试。该反应适用于具有不同空间和电子性质的各种芳基和杂芳基碘化物。它提供了良好到极好的所需产品的产率。所开发的协议在易于处理催化剂和简单的后处理程序方面是有利的；它也是一种环保工艺，具有有效的催化剂可回收性。
• Pyrimidine compounds
  申请人：——

  公开号：US20040077642A1

  公开（公告）日：2004-04-22

  The present invention relates to new compounds of the formula (I) a process for their preparation, pharmaceutical formulations containing said therapeutically active compounds and to the use of said active compounds in therapy, as well as intermediates used in the preparation of said active compounds. 1

  本发明涉及公式（I）的新化合物，其制备过程，含有该治疗活性化合物的制药配方以及在治疗中使用该活性化合物，以及用于制备该活性化合物的中间体。
• (DIAZOLO-PYRIDINYL)-PYRIMIDINES FOR USE IN TREATMENT OF CNS DISORDERS AND DIABETES
  申请人：AstraZeneca AB

  公开号：EP1373266A2

  公开（公告）日：2004-01-02
• US7345050B2
  申请人：——

  公开号：US7345050B2

  公开（公告）日：2008-03-18