10-(dimethylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-(dimethylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane
• 英文别名: [1-dimethylboranyl-5-[phenyl(1H-pyrrol-2-yl)methyl]pyrrol-2-yl]-(4-methylphenyl)methanone
• 化学式: C₂₅H₂₅BN₂O
• 分子量: 380.297
• InChiKey: MVBNJRJEBNBLKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  10-(9-borabicyclo[3.3.1]non-9-yl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 在 戊醇 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 10-(dimethylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane
  参考文献：
  名称：

  Boron-Complexation Strategy for Use with 1-Acyldipyrromethanes

  摘要：

  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.

  DOI：

  10.1021/jo0492620

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.