4-(3-methyl-3-hydroxybut-1-yn-1-yl)benzaldehyde-formyl-13C | 945904-58-5

• 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: 4-(3-methyl-3-hydroxybut-1-yn-1-yl)benzaldehyde-formyl-13C
• 英文别名: 4-(3-hydroxy-3-methylbut-1-ynyl)benzaldehyde
• CAS: 945904-58-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 189.215
• InChiKey: SLKHCIZTANAAEH-QBZHADDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-methyl-3-hydroxybut-1-yn-1-yl)benzaldehyde-formyl-13C 、 吡咯 、 2,4,6-三甲基苯甲醛 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc diacetate 作用下， 以 氯仿 、 甲醇 为溶剂， 反应 2.0h， 以14%的产率得到5-[4-(3-methyl-3-hydroxybut-1-yn-1-yl)phenyl]-10,15,20-trimesitylporphinatozinc(II)-(5-13C)
  参考文献：
  名称：

  Meso-¹³C-Labeled Porphyrins for Studies of Ground-State Hole Transfer in Multiporphyrin Arrays

  摘要：

  Understanding electronic communication among interacting chromophores provides the foundation for a variety of applications. The ground-state electronic communication in diphenylethyne-linked zinc-porphyrin dyads has been investigated by a novel molecular design strategy that entails introduction of a C-13-atom (*) at specific sites of the porphyrins where there is substantial electron density in the relevant frontier (highest occupied) molecular orbital. The site of C-13 substitution is at a meso-position, either the site of attachment of the linker (proximal, "P") or the site trans to the linker (distal, "D"). The substituents (R) at the non-linking meso-positions are mesityl, tridec-7-yl ("swallowtail"), or p-tolyl groups. Altogether five isotopically labeled porphyrin dyads have been prepared. The hole/electron-transfer properties of one-electron oxidized dyads have been examined by electron paramagnetic resonance (EPR) spectroscopy. The introduction of the meso-C-13 label provides a "clock" (via the hyperfine interactions) that allows investigation of a time scale for hole transfer that is 3-4 times shorter than that provided by the natural abundance N-14 nuclei of the pyrrole nitrogen atoms. The EPR studies indicate that the hole transfer, which has been previously shown to be fast on the time scale of the N-14 hyperfine clock (similar to 220 ns), remains fast on the time scale of the C-13 hyperfine clock (similar to 50 ns).

  DOI：

  10.1021/jo070593x
• 作为产物：
  描述：

  4-iodobenzo<13C>nitrile 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 TEA 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-(3-methyl-3-hydroxybut-1-yn-1-yl)benzaldehyde-formyl-13C
  参考文献：
  名称：

  Meso-¹³C-Labeled Porphyrins for Studies of Ground-State Hole Transfer in Multiporphyrin Arrays

  摘要：

  Understanding electronic communication among interacting chromophores provides the foundation for a variety of applications. The ground-state electronic communication in diphenylethyne-linked zinc-porphyrin dyads has been investigated by a novel molecular design strategy that entails introduction of a C-13-atom (*) at specific sites of the porphyrins where there is substantial electron density in the relevant frontier (highest occupied) molecular orbital. The site of C-13 substitution is at a meso-position, either the site of attachment of the linker (proximal, "P") or the site trans to the linker (distal, "D"). The substituents (R) at the non-linking meso-positions are mesityl, tridec-7-yl ("swallowtail"), or p-tolyl groups. Altogether five isotopically labeled porphyrin dyads have been prepared. The hole/electron-transfer properties of one-electron oxidized dyads have been examined by electron paramagnetic resonance (EPR) spectroscopy. The introduction of the meso-C-13 label provides a "clock" (via the hyperfine interactions) that allows investigation of a time scale for hole transfer that is 3-4 times shorter than that provided by the natural abundance N-14 nuclei of the pyrrole nitrogen atoms. The EPR studies indicate that the hole transfer, which has been previously shown to be fast on the time scale of the N-14 hyperfine clock (similar to 220 ns), remains fast on the time scale of the C-13 hyperfine clock (similar to 50 ns).

  DOI：

  10.1021/jo070593x