2,6-bis(4-bromobenzyloxy)benzaldehyde | 135351-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis(4-bromobenzyloxy)benzaldehyde
• 英文别名: 2,6-bis[(4-bromophenyl)methoxy]benzaldehyde
• CAS: 135351-85-8
• 化学式: C₂₁H₁₆Br₂O₃
• 分子量: 476.164
• InChiKey: DRTOVXLRSDSELW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  吡咯 、 2,6-bis(4-bromobenzyloxy)benzaldehyde 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 meso-tetrakis<2,6-bis(4-bromobenzyloxy)phenyl>porphyrin
  参考文献：
  名称：

  面部受累卟啉的合成。一种光收集天线复合体的方法

  摘要：

  通过两步式一瓶室温卟啉合成，将2，6-二和2,4,6-三苄氧基苯甲醛以9-52％的产率转化为相应的八-和十二-苄氧基卟啉。

  DOI：

  10.1016/s0040-4039(00)74308-5
• 作为产物：
  描述：

  2,6-二甲氧基苯甲醛 在 aluminum tri-bromide 、 potassium carbonate 作用下， 以 二硫化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,6-bis(4-bromobenzyloxy)benzaldehyde
  参考文献：
  名称：

  Synthesis of porphyrins tailored with eight facially-encumbering groups. An approach to solid-state light-harvesting complexes

  摘要：

  Synthetic models of the photosynthetic antenna complexes must achieve long-range 3-dimensional order encompassing a large number of porphyrinic pigments with limited direct contact of the pigments. In order to develop solid-state antenna complexes, we have synthesized porphyrins bearing benzyloxy groups projecting over both faces and optionally also around the periphery of the porphyrin. Routes have been established for prefunctionalizing benzaldehydes with various benzyloxy groups. Reaction of 2,6-bis, 3,5-bis, or 2,4,6-tris(benzyloxy)benzaldehydes with pyrrole via the room temperature two-step one-flask porphyrin reaction provides direct access to the facially-encumbered porphyrins. The benzyloxybenzaldehydes react as efficiently as methoxybenzaldehydes, indicating the utility of the -OCH2- unit for introducing large substituents near the face of the porphyrin. The octakis and dodecakis(benzyloxy)porphyrins exhibit characteristic porphyrin absorption and fluorescence properties in solution. The crystal structure of meso-tetrakis[2,6-bis(2,3 4,5,6-pentafluorobenzyloxy)phenyl] porphyrin has been determined. The pentafluorobenzyloxy substituents provide a cavity on each side of the porphyrin plane which has an approximate cylindrical shape with a diameter of similar to 7.5 Angstrom and a height of greater than or equal to 4.5 Angstrom. The porphyrin core parameters are those obtained for free base derivatives in which the inner hydrogen atoms are ordered. Crystal data: a = 14.759(1) Angstrom, b = 25.519 (2) Angstrom, c = 13.100(1) Angstrom, alpha = 100.04(1), beta = 99.83 (1), gamma = 88.25(1), V = 4767.3 (6) Angstrom(3), all measurements at 127 K, triclinic, space group P-1(-), Z = 2 R(1)(F) = 0.097, for 10020 ''observed'' data, and wR(2)(F-2) = 0.275 for 17761 total unique (all) data.

  DOI：

  10.1016/s0040-4020(01)89413-8