1-(pentafluorobenzoyl)dipyrromethane | 682153-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(pentafluorobenzoyl)dipyrromethane
• 英文别名: (2,3,4,5,6-pentafluorophenyl)-[5-(1H-pyrrol-2-ylmethyl)-1H-pyrrol-2-yl]methanone
• CAS: 682153-15-7
• 化学式: C₁₆H₉F₅N₂O
• 分子量: 340.252
• InChiKey: HXDCRMXUVXANPR-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  517.8±50.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(pentafluorobenzoyl)dipyrromethane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis of phenylethyne-linked porphyrin dyads

  摘要：

  Four new porphyrin dyads have been prepared for studies in artificial photosynthesis. The two porphyrins are joined at the meso positions via a phenylethyne linker and are present in zinc/zinc or zinc/free base metalation states. The porphyrin bearing the ethynyl unit incorporates zero, one, or two pentafluorophenyl groups at non-linking meso positions for tuning the porphyrin redox potentials. The synthetic approach entailed Pd-mediated coupling of porphyrin building blocks that bear a single ethynylphenyl or bromo/iodo substituent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.003
• 作为产物：
  描述：

  2,2'-二吡咯基甲烷 、 S-2-pyridyl pentafluorobenzothioate 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.84h， 以59%的产率得到1-(pentafluorobenzoyl)dipyrromethane
  参考文献：
  名称：

  Synthesis of phenylethyne-linked porphyrin dyads

  摘要：

  Four new porphyrin dyads have been prepared for studies in artificial photosynthesis. The two porphyrins are joined at the meso positions via a phenylethyne linker and are present in zinc/zinc or zinc/free base metalation states. The porphyrin bearing the ethynyl unit incorporates zero, one, or two pentafluorophenyl groups at non-linking meso positions for tuning the porphyrin redox potentials. The synthetic approach entailed Pd-mediated coupling of porphyrin building blocks that bear a single ethynylphenyl or bromo/iodo substituent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.003

文献信息

• Boron-Complexation Strategy for Use with 1-Acyldipyrromethanes
  作者：Kannan Muthukumaran、Marcin Ptaszek、Bruce Noll、W. Robert Scheidt、Jonathan S. Lindsey

  DOI：10.1021/jo0492620

  日期：2004.8.1

  1-Acyldipyrromethanes are important precursors in rational syntheses of diverse porphyrinic compounds. 1-Acyldipyrromethanes are difficult to purify, typically streaking upon chromatography and giving amorphous powders upon attempted crystallization. A solution to this problem has been achieved by reacting the 1-acyldipyrromethane with a dialkylboron triflate (e.g., Bu2B-OTf or 9-BBN-OTf) to give the corresponding B,B-dialkyl-B-(1-acyldipyrromethane)boron(III) complex. The reaction is selective for a 1-acyldipyrromethane in the presence of a dipyrromethane. The 1-acyldipyrromethane-boron complexes are stable to routine handling, are soluble in common organic solvents, are hydrophobic, crystallize readily, and chromatograph without streaking. The 1-acyldipyrromethane can be liberated in high yield from the boron complex upon treatment with 1-pentanol. Alternatively, the 1-acyldipyrromethane-boron complex can be used in the formation of a trans-A(2)B(2)-porphyrin. In summary, the boron-complexation strategy has broad scope and greatly facilitates the isolation of 1-acyldipyrromethanes.