1-[1-(9-borabicyclo[3.3.1]nonan-9-yl)-5-[1-[5-(4-methylbenzoyl)-1H-pyrrol-2-yl]hexyl]pyrrol-2-yl]hexan-1-one | 816454-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[1-(9-borabicyclo[3.3.1]nonan-9-yl)-5-[1-[5-(4-methylbenzoyl)-1H-pyrrol-2-yl]hexyl]pyrrol-2-yl]hexan-1-one
• CAS: 816454-97-4
• 化学式: C₃₆H₄₉BN₂O₂
• 分子量: 552.608
• InChiKey: GUCZMZBUYMLDCH-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C (decomp)
• 沸点：
  699.2±65.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲酰氯 在 magnesium,1,3,5-trimethylbenzene-6-ide,bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 1-[1-(9-borabicyclo[3.3.1]nonan-9-yl)-5-[1-[5-(4-methylbenzoyl)-1H-pyrrol-2-yl]hexyl]pyrrol-2-yl]hexan-1-one
  参考文献：
  名称：

  9-Acylation of 1-Acyldipyrromethanes Containing a Dialkylboron Mask for the α-Acylpyrrole Motif

  摘要：

  1,9-Diacyldipyrromethanes are important precursors to porphyrins, yet synthetic access remains limited owing to (1) poor conversion in the 9-acylation of 1-acyldipyrromethanes and (2) handling difficulties because acy1dipyrromethanes typically streak upon chromatography and give amorphous powders upon attempted crystallization. A reliable means for converting a dipyrromethane to a 1-acyldipyrromethane-dialkylboron complex was recently developed, where the dialkylboron (BR2) unit renders the complex hydrophobic and thereby facilitates isolation. Herein a refined preparation of 1,9-diacyldipyrromethanes is presented that employs the 1-acyldipyrromethane-BR2 complex as a substrate for 9-acylation. The dialkylboron unit provides protection for the alpha-acylpyrrole unit. 9-Acylation requires formation of the pyrrolyl-MgBr reagent and the presence of 1 equiv of a nonnucleophilic base to quench the proton liberated upon alpha-acylation. Reaction of the 1-acyldipyrromethane-BR2 complex (1 equiv) with mesitylmagnesium. bromide (2 equiv) followed by the addition of an acylating agent (S-2-pyridyl thioate or acid chloride, 1.1 equiv) gives the corresponding 1,9-diacyldipyrromethane-BR2 complex. The acylation method afforded 1,9-diacyldipyrromethaneBR(2) complexes with limited or no chromatography in yields of 64-92%. The 1,9-diacyldipyrromethane-BR2 complexes are stable to routine handling, are readily soluble in common organic solvents, crystallize readily, and can now be prepared in multigram quantities through use of stoichiometric quantities of reagents.

  DOI：

  10.1021/jo048587d

文献信息

• 9-Acylation of 1-Acyldipyrromethanes Containing a Dialkylboron Mask for the α-Acylpyrrole Motif
  作者：Syeda Huma H. Zaidi、Kannan Muthukumaran、Shun-ichi Tamaru、Jonathan S. Lindsey

  DOI：10.1021/jo048587d

  日期：2004.11.1

  1,9-Diacyldipyrromethanes are important precursors to porphyrins, yet synthetic access remains limited owing to (1) poor conversion in the 9-acylation of 1-acyldipyrromethanes and (2) handling difficulties because acy1dipyrromethanes typically streak upon chromatography and give amorphous powders upon attempted crystallization. A reliable means for converting a dipyrromethane to a 1-acyldipyrromethane-dialkylboron complex was recently developed, where the dialkylboron (BR2) unit renders the complex hydrophobic and thereby facilitates isolation. Herein a refined preparation of 1,9-diacyldipyrromethanes is presented that employs the 1-acyldipyrromethane-BR2 complex as a substrate for 9-acylation. The dialkylboron unit provides protection for the alpha-acylpyrrole unit. 9-Acylation requires formation of the pyrrolyl-MgBr reagent and the presence of 1 equiv of a nonnucleophilic base to quench the proton liberated upon alpha-acylation. Reaction of the 1-acyldipyrromethane-BR2 complex (1 equiv) with mesitylmagnesium. bromide (2 equiv) followed by the addition of an acylating agent (S-2-pyridyl thioate or acid chloride, 1.1 equiv) gives the corresponding 1,9-diacyldipyrromethane-BR2 complex. The acylation method afforded 1,9-diacyldipyrromethaneBR(2) complexes with limited or no chromatography in yields of 64-92%. The 1,9-diacyldipyrromethane-BR2 complexes are stable to routine handling, are readily soluble in common organic solvents, crystallize readily, and can now be prepared in multigram quantities through use of stoichiometric quantities of reagents.