2-hexyl-5-nitrobenzofuran | 1228178-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-hexyl-5-nitrobenzofuran
• 英文别名: 2-hexyl-5-nitrobenzo[b]furan；2-Hexyl-5-nitro-1-benzofuran
• CAS: 1228178-69-5
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: GMQKHKFWKCHDIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-辛炔 、 2-溴-4-硝基乙酸苯酯 在 copper(l) iodide 、 sodium tetrachloropalladate(II) 、 四甲基乙二胺 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-hexyl-5-nitrobenzofuran
  参考文献：
  名称：

  Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates

  摘要：

  Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/Cul system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.072

文献信息

• Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins
  作者：Upendra Sharma、Togati Naveen、Arun Maji、Srimanta Manna、Debabrata Maiti

  DOI：10.1002/anie.201305326

  日期：2013.11.25

  Triple CH functionalization: Palladium‐catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential CH functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

  三重CH官能化：描述了通过酚与未活化的烯烃反应，钯催化合成苯并呋喃和香豆素。该反应包括顺序的CH官能化，并显示出各种官能团相容性。初步的机理研究阐明了可能的机制。
• Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates
  作者：Antonella Bochicchio、Lucia Chiummiento、Maria Funicello、Maria Teresa Lopardo、Paolo Lupattelli

  DOI：10.1016/j.tetlet.2010.03.072

  日期：2010.5

  Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/Cul system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields. (C) 2010 Elsevier Ltd. All rights reserved.