Benzyl 5-formyl-3-hexyl-4-methylpyrrole-2-carboxylate | 185621-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl 5-formyl-3-hexyl-4-methylpyrrole-2-carboxylate
• CAS: 185621-37-8
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: LLUYQFGDFSJAEO-UHFFFAOYSA-N

物化性质

• 沸点：
  506.7±50.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Benzyl 5-formyl-3-hexyl-4-methylpyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 氧气 、 碳酸氢钠 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.16h， 生成 2,8-Dihexyl-3,7-dimethyl-5,15-diphenylporphyrin
  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：

  Methyl 3-hexyl-4-methylpyrrole-2-carboxylate 在 sodium acetate 、 sodium 、 三氯氧磷 作用下， 反应 30.17h， 生成 Benzyl 5-formyl-3-hexyl-4-methylpyrrole-2-carboxylate
  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