1-pentafluorobenzoyl-5,5-dimethyldipyrromethane | 1205673-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-pentafluorobenzoyl-5,5-dimethyldipyrromethane
• 英文别名: (2,3,4,5,6-pentafluorophenyl)-[5-[2-(1H-pyrrol-2-yl)propan-2-yl]-1H-pyrrol-2-yl]methanone
• CAS: 1205673-81-9
• 化学式: C₁₈H₁₃F₅N₂O
• 分子量: 368.306
• InChiKey: VVTGNOUMUBWFAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-5,5-dimethyldipyrromethane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2,3,4,5,6-pentafluorophenyl)-[5-[2-(1H-pyrrol-2-yl)propan-2-yl]-1H-pyrrol-2-yl]methanol
  参考文献：
  名称：

  Investigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole

  摘要：

  Two complementary dipyrromethane + dipyrromethanemonocarbinol routes to a meso-substituted 5-isocorrole were investigated. While both routes could afford the identical 5-isocorrole, self-condensation of the different dipyrromethanemonocarbinol precursors could potentially lead to a second porphyrinoid of different structure (a porphyrin or a porphodimethene). The two reaction routes were examined to compare the distribution of porphyrinoid products, probe the effect of key reaction parameters on the product distribution, and identify conditions for the efficient preparation of the 5-isocorrole so that its spectral properties and stability toward light and air could be assessed. For each route, a systematic survey of reaction parameters was performed via analytical-scale reactions monitored for the yields of the 5-isocorrole and self-condensation product by HPLC. The two reaction routes were found to afford very different product distributions in accordance with the anticipated nucleophilicity of the dipyrromethane and dipyrromethanemonocarbinol precursors. The most promising reaction condition (InCl3, 0.32 mM) was performed on a preparative-scale providing the 5-isocorrole in an isolated yield of 31 % (102 mg). Spectroscopic analysis was consistent with the 5-isocorrole Structure. The stability of the 5-isocorrole in dilute solution upon exposure to light and air was assessed by UV-vis spectroscopy and HPLC and was found to be excellent.

  DOI：

  10.1021/jo902452c
• 作为产物：
  描述：

  2,2'-(2,2-丙烷二基)二(1H-吡咯) 、 S-2-pyridyl pentafluorobenzothioate 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到1-pentafluorobenzoyl-5,5-dimethyldipyrromethane
  参考文献：
  名称：

  Investigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole

  摘要：

  Two complementary dipyrromethane + dipyrromethanemonocarbinol routes to a meso-substituted 5-isocorrole were investigated. While both routes could afford the identical 5-isocorrole, self-condensation of the different dipyrromethanemonocarbinol precursors could potentially lead to a second porphyrinoid of different structure (a porphyrin or a porphodimethene). The two reaction routes were examined to compare the distribution of porphyrinoid products, probe the effect of key reaction parameters on the product distribution, and identify conditions for the efficient preparation of the 5-isocorrole so that its spectral properties and stability toward light and air could be assessed. For each route, a systematic survey of reaction parameters was performed via analytical-scale reactions monitored for the yields of the 5-isocorrole and self-condensation product by HPLC. The two reaction routes were found to afford very different product distributions in accordance with the anticipated nucleophilicity of the dipyrromethane and dipyrromethanemonocarbinol precursors. The most promising reaction condition (InCl3, 0.32 mM) was performed on a preparative-scale providing the 5-isocorrole in an isolated yield of 31 % (102 mg). Spectroscopic analysis was consistent with the 5-isocorrole Structure. The stability of the 5-isocorrole in dilute solution upon exposure to light and air was assessed by UV-vis spectroscopy and HPLC and was found to be excellent.

  DOI：

  10.1021/jo902452c

文献信息

• Investigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole
  作者：Danette L. Flint、Rachel L. Fowler、Timothy D. LeSaulnier、Andrew C. Long、Anna Y. O’Brien、G. Richard Geier

  DOI：10.1021/jo902452c

  日期：2010.2.5

  Two complementary dipyrromethane + dipyrromethanemonocarbinol routes to a meso-substituted 5-isocorrole were investigated. While both routes could afford the identical 5-isocorrole, self-condensation of the different dipyrromethanemonocarbinol precursors could potentially lead to a second porphyrinoid of different structure (a porphyrin or a porphodimethene). The two reaction routes were examined to compare the distribution of porphyrinoid products, probe the effect of key reaction parameters on the product distribution, and identify conditions for the efficient preparation of the 5-isocorrole so that its spectral properties and stability toward light and air could be assessed. For each route, a systematic survey of reaction parameters was performed via analytical-scale reactions monitored for the yields of the 5-isocorrole and self-condensation product by HPLC. The two reaction routes were found to afford very different product distributions in accordance with the anticipated nucleophilicity of the dipyrromethane and dipyrromethanemonocarbinol precursors. The most promising reaction condition (InCl3, 0.32 mM) was performed on a preparative-scale providing the 5-isocorrole in an isolated yield of 31 % (102 mg). Spectroscopic analysis was consistent with the 5-isocorrole Structure. The stability of the 5-isocorrole in dilute solution upon exposure to light and air was assessed by UV-vis spectroscopy and HPLC and was found to be excellent.