1,9-diformyl-5-trifluoromethyldipyrromethane | 351884-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,9-diformyl-5-trifluoromethyldipyrromethane
• 英文别名: 5-[2,2,2-trifluoro-1-(5-formyl-1H-pyrrol-2-yl)ethyl]-1H-pyrrole-2-carbaldehyde
• CAS: 351884-81-6
• 化学式: C₁₂H₉F₃N₂O₂
• 分子量: 270.211
• InChiKey: XBIYEDZJIFCYFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,9-diformyl-5-trifluoromethyldipyrromethane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 dipyrromethane-1,9-dicarbinol
  参考文献：
  名称：

  Design and synthesis of manganese porphyrins with tailored lipophilicity: Investigation of redox properties and superoxide dismutase activity

  摘要：

  Thirteen new manganese porphyrins and two porphodimethenes bearing one to three different substituents at the meso positions in a variety of architectures have been synthesized. The substituents employed generally are (i) electron-withdrawing to time the reduction potential to the desirable range (near +0.3 V vs NHE), and/or (ii) lipophilic to target the interior of lipid bilayer membranes and/or the blood-brain barrier. The influence of the substituents on the Mn-II /Mn-II reduction potentials has been characterized. and the superoxide disimutase activity of the compounds has been examined. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.015
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 5-(trifluoromethyl)dipyrromethane 在 三氯氧磷 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到1,9-diformyl-5-trifluoromethyldipyrromethane
  参考文献：
  名称：

  Investigations on the directive effects of a single meso-substituent via nitration of 5,12,13,17,18-pentasubstituted porphyrins: syntheses of conjugated β-nitroporphyrins

  摘要：

  Vilsmeier formylation of 5-substituted 1,9-diunsubstituted dipyrromethanes afforded 1,9-diformyldipyrromethanes in good yields. Their MacDonald condensation with tetra-beta -alkyldipyrromethanes produced 5,12,13,17,18-pentasubstituted porphyrins. A mesoelectron-donating group, presumably acting by destabilizing the porphyrin at, ground state, directs the nitrations to the mese-carbons. beta -Nitration takes place on porphyrins bearing a meso-electron-withdrawing group. Unhindered beta -nitro groups are shown to exert stronger electronic effects relative to meso-nitro groups by conjugating effectively with the porphyrin macrocycle. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00329-5

文献信息

• Design and synthesis of manganese porphyrins with tailored lipophilicity: Investigation of redox properties and superoxide dismutase activity
  作者：Dorothée Lahaye、Kannan Muthukumaran、Chen-Hsiung Hung、Dorota Gryko、Júlio S. Rebouças、Ivan Spasojević、Ines Batinić-Haberle、Jonathan S. Lindsey

  DOI：10.1016/j.bmc.2007.07.015

  日期：2007.11

  Thirteen new manganese porphyrins and two porphodimethenes bearing one to three different substituents at the meso positions in a variety of architectures have been synthesized. The substituents employed generally are (i) electron-withdrawing to time the reduction potential to the desirable range (near +0.3 V vs NHE), and/or (ii) lipophilic to target the interior of lipid bilayer membranes and/or the blood-brain barrier. The influence of the substituents on the Mn-II /Mn-II reduction potentials has been characterized. and the superoxide disimutase activity of the compounds has been examined. (C) 2007 Elsevier Ltd. All rights reserved.
• Investigations on the directive effects of a single meso-substituent via nitration of 5,12,13,17,18-pentasubstituted porphyrins: syntheses of conjugated β-nitroporphyrins
  作者：Anura Wickramasinghe、Laurent Jaquinod、Daniel J Nurco、Kevin M Smith

  DOI：10.1016/s0040-4020(01)00329-5

  日期：2001.5

  Vilsmeier formylation of 5-substituted 1,9-diunsubstituted dipyrromethanes afforded 1,9-diformyldipyrromethanes in good yields. Their MacDonald condensation with tetra-beta -alkyldipyrromethanes produced 5,12,13,17,18-pentasubstituted porphyrins. A mesoelectron-donating group, presumably acting by destabilizing the porphyrin at, ground state, directs the nitrations to the mese-carbons. beta -Nitration takes place on porphyrins bearing a meso-electron-withdrawing group. Unhindered beta -nitro groups are shown to exert stronger electronic effects relative to meso-nitro groups by conjugating effectively with the porphyrin macrocycle. (C) 2001 Elsevier Science Ltd. All rights reserved.