1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole | 645414-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole
• 英文别名: 1-Benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-benzo[d]imidazole；1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzimidazole
• CAS: 645414-75-1
• 化学式: C₂₀H₂₃BN₂O₂
• 分子量: 334.226
• InChiKey: GSLCPERDWTXHJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole 在 四(三苯基膦)钯 potassium phosphate 、 1,2-二碘乙烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,1'-Dibenzyl-2'-iodo-6-phenyl-1H,1'H-[2,5']bibenzoimidazolyl
  参考文献：
  名称：

  Synthesis of a terbenzimidazole topoisomerase I poison via iterative borinate ester couplings

  摘要：

  A concise, efficient synthesis is described for a terbenzimidazole that acts as a potent topoisomerase I poison. The strategy involves iterative palladium-catalyzed borinate ester cross-couplings and should be applicable to the synthesis of analogs containing heterocycles other than benzimidazole. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.007
• 作为产物：
  描述：

  4-碘-1,2-苯二胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 氢氧化钾 、 KSF clay 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of a terbenzimidazole topoisomerase I poison via iterative borinate ester couplings

  摘要：

  A concise, efficient synthesis is described for a terbenzimidazole that acts as a potent topoisomerase I poison. The strategy involves iterative palladium-catalyzed borinate ester cross-couplings and should be applicable to the synthesis of analogs containing heterocycles other than benzimidazole. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.007

文献信息

• Synthesis of a terbenzimidazole topoisomerase I poison via iterative borinate ester couplings
  作者：Ben B. Wang、Paul J. Smith

  DOI：10.1016/j.tetlet.2003.10.007

  日期：2003.12

  A concise, efficient synthesis is described for a terbenzimidazole that acts as a potent topoisomerase I poison. The strategy involves iterative palladium-catalyzed borinate ester cross-couplings and should be applicable to the synthesis of analogs containing heterocycles other than benzimidazole. (C) 2003 Elsevier Ltd. All rights reserved.