4-Hexyl-5-carbomethoxy-3-methylpyrrole-2-carboxylic acid | 185621-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-Hexyl-5-carbomethoxy-3-methylpyrrole-2-carboxylic acid
• 英文别名: 4-hexyl-5-methoxycarbonyl-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 185621-35-6
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: NJMUTJYTIXZESE-UHFFFAOYSA-N

物化性质

• 沸点：
  460.5±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  79.39
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Hexyl-5-carbomethoxy-3-methylpyrrole-2-carboxylic acid 在 platinum(IV) oxide 氢气 、 碘 、 sodium acetate 、 sodium 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.17h， 生成 1,9-(Dibenzyloxycarbonyl)-2,8-dihexyl-3,7-dimethyl-5-phenyldipyrromethane
  参考文献：
  名称：

  Aryl Ring Rotation in Porphyrins. A Carbon-13 NMR Spin−Lattice Relaxation Time Study

  摘要：

  Overall tumbling and internal rotational motions in porphyrins bearing meso aryl substituents and, in some cases, flanking alkyl groups at the beta-pyrrolic positions have been determined using C-13 spin-lattice relaxation time measurements. In deuteriochloroform solution at 303 K, the overall reorientation of all three porphyrins investigated occurs with diffusion coefficients of similar to 1 x 10(9) s(-1). In porphyrins with only hydrogen at the beta-pyrrolic positions, the meso phenyl rings undergo rotations about their single bonds to the porphyrin with diffusion coefficients of similar to 4 x 10(9) s(-1). Introduction of methyl substituents at the beta-pyrrolic positions adjacent to the phenyl rings reduces these motions, but only to similar to 1 x 10(9) s(-1). Thus, significant internal motions are present in both types of molecules. These motions occur on the time scale of many photoinduced electron and energy transfer processes in porphyrins covalently linked to electron or energy donors or accepters through meso aryl groups. Thus, the internal librational motions may affect rates of photoinduced electron and energy transfer, even in relatively ''rigid'' molecular constructs.

  DOI：

  10.1021/jp962209y
• 作为产物：
  描述：

  ethyl 4-hexyl-3,5-dimethylpyrrole-2-carboxylate 在 palladium on activated charcoal 磺酰氯 、 氢气 、 sodium acetate 、 sodium 作用下， 以 四氢呋喃 为溶剂， 50.0~90.0 ℃ 、2.13 kPa 条件下， 反应 37.0h， 生成 4-Hexyl-5-carbomethoxy-3-methylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  Aryl Ring Rotation in Porphyrins. A Carbon-13 NMR Spin−Lattice Relaxation Time Study

  摘要：

  Overall tumbling and internal rotational motions in porphyrins bearing meso aryl substituents and, in some cases, flanking alkyl groups at the beta-pyrrolic positions have been determined using C-13 spin-lattice relaxation time measurements. In deuteriochloroform solution at 303 K, the overall reorientation of all three porphyrins investigated occurs with diffusion coefficients of similar to 1 x 10(9) s(-1). In porphyrins with only hydrogen at the beta-pyrrolic positions, the meso phenyl rings undergo rotations about their single bonds to the porphyrin with diffusion coefficients of similar to 4 x 10(9) s(-1). Introduction of methyl substituents at the beta-pyrrolic positions adjacent to the phenyl rings reduces these motions, but only to similar to 1 x 10(9) s(-1). Thus, significant internal motions are present in both types of molecules. These motions occur on the time scale of many photoinduced electron and energy transfer processes in porphyrins covalently linked to electron or energy donors or accepters through meso aryl groups. Thus, the internal librational motions may affect rates of photoinduced electron and energy transfer, even in relatively ''rigid'' molecular constructs.

  DOI：

  10.1021/jp962209y