5-[[5-[(5-carboxy-3-ethyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-4-ethyl-3-methyl-1H-pyrrole-2-carboxylic acid | 502759-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[[5-[(5-carboxy-3-ethyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-4-ethyl-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 502759-63-9
• 化学式: C₂₃H₂₉N₃O₄
• 分子量: 411.501
• InChiKey: RKFTVBBIBOQRBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  122
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-diformylindene 、 5-[[5-[(5-carboxy-3-ethyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-4-ethyl-3-methyl-1H-pyrrole-2-carboxylic acid 在 三氟乙酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以50%的产率得到8,17-diethyl-7,12,18-trimethyl-21-carbabenzo[b]porphyrin
  参考文献：
  名称：

  Conjugated Macrocycles Related to the Porphyrins. 25. Proton NMR Spectroscopic Evidence for a Preferred [18]Annulene Substructure in Carbaporphyrins from the Magnitude of Selected ⁴J_H,H CHCCH₃ Coupling Constants

  摘要：

  Two new benzocarbaporphyrins with four or five alkyl substituents have been synthesized by the "3 + 1" MacDonald methodology. At lower temperatures, the proton NMR spectrum of the asymmetrically substituted carbaporphyrin 8 gave two NH resonances, while carbaporphyrin 9, which retains a plane of symmetry, gave only one resonance of this kind. As no additional peaks were seen for the remaining protons, these data strongly support the proposal that a single tautomer predominates in solution where the two NH protons flank the interior CH. Carbaporphyrin 8, which has a CH=CMe unit on the pyrrolic ring opposite the indene moiety, gave a long-range coupling constant of (4)J(Me,H) = 1.3-1.4 Hz. On the other hand, the CH=CMe units of 9, which correspond to the pyrrole rings on each side of the carbocyclic moiety, gave (4)J(Me,H) = 0.9-1.0 Hz. These values are in accord with those expected if the exterior carbon-carbon bonds of the pyrrole units next to the indene ring are part of a fully delocalized 18pi electron system, while the C=C bond of the remaining pyrrole ring retains substantial olefinic character.

  DOI：

  10.1021/jo020703u
• 作为产物：
  描述：

  3-甲基-1H-吡咯-2-甲酸乙酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙二醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 34.0h， 生成 5-[[5-[(5-carboxy-3-ethyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-4-ethyl-3-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Conjugated Macrocycles Related to the Porphyrins. 25. Proton NMR Spectroscopic Evidence for a Preferred [18]Annulene Substructure in Carbaporphyrins from the Magnitude of Selected ⁴J_H,H CHCCH₃ Coupling Constants

  摘要：

  Two new benzocarbaporphyrins with four or five alkyl substituents have been synthesized by the "3 + 1" MacDonald methodology. At lower temperatures, the proton NMR spectrum of the asymmetrically substituted carbaporphyrin 8 gave two NH resonances, while carbaporphyrin 9, which retains a plane of symmetry, gave only one resonance of this kind. As no additional peaks were seen for the remaining protons, these data strongly support the proposal that a single tautomer predominates in solution where the two NH protons flank the interior CH. Carbaporphyrin 8, which has a CH=CMe unit on the pyrrolic ring opposite the indene moiety, gave a long-range coupling constant of (4)J(Me,H) = 1.3-1.4 Hz. On the other hand, the CH=CMe units of 9, which correspond to the pyrrole rings on each side of the carbocyclic moiety, gave (4)J(Me,H) = 0.9-1.0 Hz. These values are in accord with those expected if the exterior carbon-carbon bonds of the pyrrole units next to the indene ring are part of a fully delocalized 18pi electron system, while the C=C bond of the remaining pyrrole ring retains substantial olefinic character.

  DOI：

  10.1021/jo020703u

文献信息

• Conjugated Macrocycles Related to the Porphyrins. 25. Proton NMR Spectroscopic Evidence for a Preferred [18]Annulene Substructure in Carbaporphyrins from the Magnitude of Selected ⁴<i>J</i>_H,H CHCCH₃ Coupling Constants
  作者：Dachun Liu、Timothy D. Lash

  DOI：10.1021/jo020703u

  日期：2003.3.1

  Two new benzocarbaporphyrins with four or five alkyl substituents have been synthesized by the "3 + 1" MacDonald methodology. At lower temperatures, the proton NMR spectrum of the asymmetrically substituted carbaporphyrin 8 gave two NH resonances, while carbaporphyrin 9, which retains a plane of symmetry, gave only one resonance of this kind. As no additional peaks were seen for the remaining protons, these data strongly support the proposal that a single tautomer predominates in solution where the two NH protons flank the interior CH. Carbaporphyrin 8, which has a CH=CMe unit on the pyrrolic ring opposite the indene moiety, gave a long-range coupling constant of (4)J(Me,H) = 1.3-1.4 Hz. On the other hand, the CH=CMe units of 9, which correspond to the pyrrole rings on each side of the carbocyclic moiety, gave (4)J(Me,H) = 0.9-1.0 Hz. These values are in accord with those expected if the exterior carbon-carbon bonds of the pyrrole units next to the indene ring are part of a fully delocalized 18pi electron system, while the C=C bond of the remaining pyrrole ring retains substantial olefinic character.