5-Methoxy-3-phenyl-indazol | 13097-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methoxy-3-phenyl-indazol
• 英文别名: 5-methoxy-3-phenyl-1H-indazole
• CAS: 13097-05-7
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: YKEVJZLUERQOQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘吡啶 、 5-Methoxy-3-phenyl-indazol 在 potassium phosphate 、 copper(l) iodide 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以98%的产率得到5-methoxy-3-phenyl-1-(pyridin-2-yl)-1H-indazole
  参考文献：
  名称：

  Synthesis of 1,3-diarylsubstituted indazoles utilizing a Suzuki cross-coupling/deprotection/N-arylation sequence

  摘要：

  Herein we report a general synthesis of 1,3-diarylsubstituted indazoles utilizing a two-step Suzuki cross-coupling/deprotection/N-arylation sequence. This procedure proceeds in excellent overall yield starting from the 3-iodo-N-Boc indazole derivative allowing for rapid access to these compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.060
• 作为产物：
  描述：

  (2-氨基-5-甲氧基苯基)(苯基)甲酮 在 咪唑 、 盐酸羟胺 、 碘 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 5-Methoxy-3-phenyl-indazol
  参考文献：
  名称：

  Mild method for the synthesis of 1H-indazoles through oxime-phosphonium ion intermediate

  摘要：

  The synthesis of 1H-indazoles from o-aminobenzoximes is achieved via N-N bond formation using triphenylphosphine, 12, and imidazole. Selective formation of oxime-phosphonium ion intermediate in the presence of the amino group is the driving force for this reaction. The nucleophilicity of the arylamino group and electrophilicity toward the N-O bond of oxime also control the reaction. The reaction proceeds at a faster rate with good to excellent yield under this mild reaction condition and is amenable to scale-up. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.001

文献信息

• ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in <i>Candida albicans</i>
  作者：Willmen Youngsaye、Cathy L Hartland、Barbara J Morgan、Amal Ting、Partha P Nag、Benjamin Vincent、Carrie A Mosher、Joshua A Bittker、Sivaraman Dandapani、Michelle Palmer、Luke Whitesell、Susan Lindquist、Stuart L Schreiber、Benito Munoz

  DOI：10.3762/bjoc.9.171

  日期：——

  The National Institutes of Health Molecular Libraries and Probe Production Centers Network (NIH-MLPCN) screened >300,000 compounds to evaluate their ability to restore fluconazole susceptibility in resistant Candida albicans isolates. Additional counter screens were incorporated to remove substances inherently toxic to either mammalian or fungal cells. A substituted indazole possessing the desired bioactivity profile was selected for further development, and initial investigation of structure–activity relationships led to the discovery of ML212.

  国家卫生研究院分子图书馆和探针生产中心网络（NIH-MLPCN）筛选了超过300,000种化合物，以评估它们恢复对耐药念珠菌的氟康唑敏感性的能力。还加入了额外的对照筛选，以去除对哺乳动物或真菌细胞有毒的物质。选择了具有所需生物活性特征的取代吲唑化合物进行进一步开发，并初步研究结构-活性关系导致了ML212的发现。
• Rhodium(III)-Catalyzed Indazole Synthesis by C–H Bond Functionalization and Cyclative Capture
  作者：Yajing Lian、Robert G. Bergman、Luke D. Lavis、Jonathan A. Ellman

  DOI：10.1021/ja402761p

  日期：2013.5.15

  An efficient, one-step, and highly functional group-compatible synthesis of substituted N-aryl-2H-indazoles is reported via the rhodium(III)-catalyzed C-H bond addition of azobenzenes to aldehydes. The regioselective coupling of unsymmetrical azobenzenes was further demonstrated and led to the development of a new removable aryl group that allows for the preparation of indazoles without N-substitution. The 2-aryl-2H-indazole products also represent a new class of readily prepared fluorophores for which initial spectroscopic characterization has been performed.