4-溴-5-甲基-1H-吲唑-1-羧酸叔丁酯 | 926922-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 4-溴-5-甲基-1H-吲唑-1-羧酸叔丁酯
• 英文名称: 5-methyl-4-bromo-N-(tert-butoxycarbonyl)-indazole
• 英文别名: Tert-butyl 4-bromo-5-methyl-1H-indazole-1-carboxylate；tert-butyl 4-bromo-5-methylindazole-1-carboxylate
• CAS: 926922-41-0
• 化学式: C₁₃H₁₅BrN₂O₂
• 分子量: 311.178
• InChiKey: GQRYROVGFBSASA-UHFFFAOYSA-N

物化性质

• 沸点：
  393.3±34.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352+P312,P304+P340+P312,P305+P351+P338,P337+P313,P363,P403+P233,P405,P501
• 危险性描述：
  H302+H312+H332,H319,H335

反应信息

• 作为反应物：
  描述：

  N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine 、 4-溴-5-甲基-1H-吲唑-1-羧酸叔丁酯 在 palladium diacetate 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 tert-butyl 4-[(E)-2-[6-(4-dimethylphosphorylanilino)purin-9-yl]ethenyl]-5-methylindazole-1-carboxylate
  参考文献：
  名称：

  Novel N9-arenethenyl purines as potent dual Src/Abl tyrosine kinase inhibitors

  摘要：

  Novel N-9-arenethenyl purines, optimized potent dual Src/Abl tyrosine kinase inhibitors, are described. The key structural feature is a trans vinyl linkage at N-9 on the purine core which projects hydrophobic substituents into the selectivity pocket at the rear of the ATP site. Their synthesis was achieved through a Horner-Wadsworth-Emmons reaction of N-9-phosphorylmethylpurines and substituted benzaldehydes or Heck reactions between 9-vinyl purines and aryl halides. Most compounds are potent inhibitors of both Src and Abl kinase, and several possess good oral bioavailability. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.042
• 作为产物：
  描述：

  4-溴-5-甲基-1H-吲唑 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 4-溴-5-甲基-1H-吲唑-1-羧酸叔丁酯
  参考文献：
  名称：

  WO2007/21937

  摘要：

  公开号：

文献信息

• WO2007/21937
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel N9-arenethenyl purines as potent dual Src/Abl tyrosine kinase inhibitors
  作者：Yihan Wang、William C. Shakespeare、Wei-Sheng Huang、Raji Sundaramoorthi、Scott Lentini、Sasmita Das、Shuangying Liu、Geeta Banda、David Wen、Xiaotian Zhu、Qihong Xu、Jeffrey Keats、Frank Wang、Scott Wardwell、Yaoyu Ning、Joseph T. Snodgrass、Mark I. Broudy、Karin Russian、David Dalgarno、Tim Clackson、Tomi K. Sawyer

  DOI：10.1016/j.bmcl.2008.06.042

  日期：2008.9

  Novel N-9-arenethenyl purines, optimized potent dual Src/Abl tyrosine kinase inhibitors, are described. The key structural feature is a trans vinyl linkage at N-9 on the purine core which projects hydrophobic substituents into the selectivity pocket at the rear of the ATP site. Their synthesis was achieved through a Horner-Wadsworth-Emmons reaction of N-9-phosphorylmethylpurines and substituted benzaldehydes or Heck reactions between 9-vinyl purines and aryl halides. Most compounds are potent inhibitors of both Src and Abl kinase, and several possess good oral bioavailability. (C) 2008 Elsevier Ltd. All rights reserved.