2,4,6-tri(2,3,4,5,6-pentafluorobenzyloxy)benzaldehyde | 135351-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4,6-tri(2,3,4,5,6-pentafluorobenzyloxy)benzaldehyde
• 英文别名: 2,4,6-tris(pentafluorobenzyloxy)benzaldehyde；2,4,6-Tris[(2,3,4,5,6-pentafluorophenyl)methoxy]benzaldehyde
• CAS: 135351-90-5
• 化学式: C₂₈H₉F₁₅O₄
• 分子量: 694.353
• InChiKey: HZZXTXLTHDFENZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  吡咯 、 2,4,6-tri(2,3,4,5,6-pentafluorobenzyloxy)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<2,4,6-tri(2,3,4,5,6-pentafluorobenzyloxy)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：

  五氟苯甲醇 、 间苯三酚甲醛 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以40%的产率得到2,4,6-tri(2,3,4,5,6-pentafluorobenzyloxy)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

文献信息

• One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks
  作者：Chang-Hee Lee、Jonathan S. Lindsey

  DOI：10.1016/s0040-4020(01)89282-6

  日期：1994.1

  corresponding bis-dipyrromethane. The reaction of a meso-substituted dipyrromethane with an aldehyde under the conditions of the two-step one-flask porphyrin synthesis affords a direct route to trans-substituted meso-porphyrins. Acidolysis of the dipyrromethane is negligible under the conditions of the porphyrin-forming reaction. Four porphyrins bearing peripheral functional groups and facially-encumbering

  在不存在溶剂的情况下，在室温下醛与过量的吡咯的反应得到内消旋取代的二吡咯甲烷。该反应催化的用三氟乙酸或用BF 3 SO（ET）2。通过结晶或通过在二氧化硅上用含有1％三乙胺的洗脱液的快速色谱法纯化二吡咯甲烷。该反应与脂族或芳族醛，包括2，6-二取代的苯甲醛兼容。以这种方式制备了九种二吡咯甲烷，产率为47-86％，表明反应的范围很广。二吡咯甲烷在没有光和空气的情况下以纯化形式稳定。与对苯二甲醛和吡咯的类似反应得到相应的双-二吡咯甲烷。一个的反应内消旋取代的二吡咯甲烷与醛两步一个烧瓶中卟啉合成，得到一个直接的路线的条件下，以反式-取代的内消旋-卟啉。在形成卟啉的条件下，二吡咯甲烷的酸解作用可以忽略不计。已制备了带有外围官能团和面部阻碍基团的四种卟啉，它们是线性卟啉阵列合成中的关键组成部分。
• Synthesis of porphyrins tailored with eight facially-encumbering groups. An approach to solid-state light-harvesting complexes
  作者：Richard W. Wagner、Jonathan S. Lindsey、Ilona Turowska-Tyrk、W.Robert Scheidt

  DOI：10.1016/s0040-4020(01)89413-8

  日期：——

  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.
• Synthesis of facially-encumbered porphyrins. An approach to light-harvesting antenna complexes
  作者：Richard W. Wagner、James Ruffing、Bradly V. Breakwell、Jonathan S. Lindsey

  DOI：10.1016/s0040-4039(00)74308-5

  日期：1991.4

  2,6-di- and 2,4,6-tri-benzyloxybenzaldehydes are converted to the respective octa- and dodeca-benzyloxy porphyrins in 9–52% yields via the two-step one-flask room-temperature porphyrin synthesis.

  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。