2-(4-iodobenzoyl)furan | 15817-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-iodobenzoyl)furan
• 英文别名: 2-Furyl(4-iodophenyl)methanone；furan-2-yl-(4-iodophenyl)methanone
• CAS: 15817-35-3
• 化学式: C₁₁H₇IO₂
• 分子量: 298.08
• InChiKey: ZAONVMBVYWJHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-iodobenzoyl)furan 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.17h， 以99%的产率得到2-[α-(p-iodophenyl)-α-hydroxymethyl]furan
  参考文献：
  名称：

  Rational Synthesis of Trans-Substituted Porphyrin Building Blocks Containing One Sulfur or Oxygen Atom in Place of Nitrogen at a Designated Site

  摘要：

  The use of heteroatom-substituted porphyrins in bioorganic and materials chemistry requires the ability to position a variety of substituents in a controlled manner about the porphyrin periphery. We describe a rational route to trans-AB(2)C-type porphyrins bearing one oxygen atom (N3O) or one sulfur atom (NBS) in a designated location in the porphyrin core. The synthesis involved four stages: (1) Acid-catalyzed condensation of a furyl- or thienylcarbinol in excess pyrrole afforded the aryl-substituted furyl- or thienylpyrromethane in high yield. (2) Treatment of the furyl- or thienylpyrromethane with an acid chloride catalyzed by SnCl4 or AlCl3 afforded the corresponding diketo product. (3) Reduction with NaBH4 in alcoholic solvents gave the furyl- or thienylpyrromethanediols. (4) Reaction of a furylpyrromethanediol, thienylpyrromethanediol, or dipyrromethanediol with a dipyrromethane in a one-flask process of condensation followed by oxidation gave the corresponding porphyrin. Reaction conditions previously identified to minimize scrambling in a dipyrromethane-aldehyde condensation were found to be effective in this application. Thus, reaction with 10 mM reactants in acetonitrile at 0 degrees C containing BF3 . Et2O and NH4Cl followed by oxidation with DDQ resulted in the desired porphyrin(10-20% yields) without acidolysis. In this manner, N3O-, N3S-, or Na-porphyrins bearing 5-(p-iodophenyl), 15-[4-(2-(trimethylsilyl)ethynyl)phenyl], and 10,20-di-p-tolyl groups have been made. This set of trans-substituted porphyrin building blacks is expected to be useful in the synthesis of biomimetic energy transduction systems.

  DOI：

  10.1021/jo9909305
• 作为产物：
  描述：

  在 碘甲烷 作用下， 反应 24.0h， 以90%的产率得到2-(4-iodobenzoyl)furan
  参考文献：
  名称：

  Preparation of Polyfunctional Arylmagnesium Reagents Bearing a Triazene Moiety. A New Carbazole Synthesis

  摘要：

  The reaction of iodo- or bromo-substituted aryltriazenes with i-PrMgCI-LiCl generates the corresponding magnesiated derivatives which react with various electrophiles (acid chlorides, 3-iodoenones, allylic halides, aidehydes) affording polyfunctional triazenes. They can be readily converted to the corresponding polyfunctional aryl iodides. This new synthetic strategy was applied to prepare functionalized carbazoles.

  DOI：

  10.1021/ol0505454

文献信息

• Preparation of Polyfunctional Arylmagnesium Reagents Bearing a Triazene Moiety. A New Carbazole Synthesis
  作者：Ching-Yuan Liu、Paul Knochel

  DOI：10.1021/ol0505454

  日期：2005.6.1

  The reaction of iodo- or bromo-substituted aryltriazenes with i-PrMgCI-LiCl generates the corresponding magnesiated derivatives which react with various electrophiles (acid chlorides, 3-iodoenones, allylic halides, aidehydes) affording polyfunctional triazenes. They can be readily converted to the corresponding polyfunctional aryl iodides. This new synthetic strategy was applied to prepare functionalized carbazoles.
• Rational Synthesis of Trans-Substituted Porphyrin Building Blocks Containing One Sulfur or Oxygen Atom in Place of Nitrogen at a Designated Site
  作者：Won-Seob Cho、Han-Je Kim、Benjamin J. Littler、Mark A. Miller、Chang-Hee Lee、Jonathan S. Lindsey

  DOI：10.1021/jo9909305

  日期：1999.10.1

  The use of heteroatom-substituted porphyrins in bioorganic and materials chemistry requires the ability to position a variety of substituents in a controlled manner about the porphyrin periphery. We describe a rational route to trans-AB(2)C-type porphyrins bearing one oxygen atom (N3O) or one sulfur atom (NBS) in a designated location in the porphyrin core. The synthesis involved four stages: (1) Acid-catalyzed condensation of a furyl- or thienylcarbinol in excess pyrrole afforded the aryl-substituted furyl- or thienylpyrromethane in high yield. (2) Treatment of the furyl- or thienylpyrromethane with an acid chloride catalyzed by SnCl4 or AlCl3 afforded the corresponding diketo product. (3) Reduction with NaBH4 in alcoholic solvents gave the furyl- or thienylpyrromethanediols. (4) Reaction of a furylpyrromethanediol, thienylpyrromethanediol, or dipyrromethanediol with a dipyrromethane in a one-flask process of condensation followed by oxidation gave the corresponding porphyrin. Reaction conditions previously identified to minimize scrambling in a dipyrromethane-aldehyde condensation were found to be effective in this application. Thus, reaction with 10 mM reactants in acetonitrile at 0 degrees C containing BF3 . Et2O and NH4Cl followed by oxidation with DDQ resulted in the desired porphyrin(10-20% yields) without acidolysis. In this manner, N3O-, N3S-, or Na-porphyrins bearing 5-(p-iodophenyl), 15-[4-(2-(trimethylsilyl)ethynyl)phenyl], and 10,20-di-p-tolyl groups have been made. This set of trans-substituted porphyrin building blacks is expected to be useful in the synthesis of biomimetic energy transduction systems.