6,7-Dibutoxy-16,23-diazatetracyclo[20.4.0.04,9.012,17]hexacosa-1(22),4,6,8,12(17),13,15,23,25-nonaen-2,10,18,20-tetrayne | 1005340-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,7-Dibutoxy-16,23-diazatetracyclo[20.4.0.04,9.012,17]hexacosa-1(22),4,6,8,12(17),13,15,23,25-nonaen-2,10,18,20-tetrayne
• CAS: 1005340-04-4
• 化学式: C₃₂H₂₆N₂O₂
• 分子量: 470.571
• InChiKey: ICQJPPHYRGLDMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[2-[4,5-Dibutoxy-2-[2-(2-ethynylpyridin-3-yl)ethynyl]phenyl]ethynyl]-2-ethynylpyridine 在 copper(l) iodide 、 1,2-二(二苯基膦基)乙烷二氯化钯(II) air 、 碘 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 以40%的产率得到6,7-Dibutoxy-16,23-diazatetracyclo[20.4.0.04,9.012,17]hexacosa-1(22),4,6,8,12(17),13,15,23,25-nonaen-2,10,18,20-tetrayne
  参考文献：
  名称：

  Synthesis, Spectroscopy, and Theoretical Calculations for a Series of Push−Pull [14]-Pyridoannulenes

  摘要：

  [GRAPHICS]Three new isomeric dipyridoannulenes were synthesized and characterized. These molecules possess differing conjugation pathways between the substituent alkoxy donating groups and the pyridyl acceptor groups. Optical absorption and emission properties of the dipyridoannulenes and their corresponding acyclic precursors were measured and correlated to structural differences and used to evaluate conjugation effectiveness and charge-transfer pathways. Optical properties of protonated dipyridoannulenes were also measured and found to be somewhat insensitive to the degree of protonation. Density functional studies of these systems at the B3LYP/6-31G* level provided insight into their stabilities, polarities, and quinoidal character. An analysis of the HOMO and LUMO molecular orbitals provided further information regarding charge-transfer behavior. These systems are good metal binding candidates, as the pyridine moiety can act as both an electron-acceptor and a site for metal coordination.

  DOI：

  10.1021/jo7019724

文献信息

• Synthesis, Spectroscopy, and Theoretical Calculations for a Series of Push−Pull [14]-Pyridoannulenes
  作者：Matthew G. Lauer、James W. Leslie、Ashley Mynar、Shelly A. Stamper、Anthony D. Martinez、Adrian J. Bray、Senai Negassi、Kevin McDonald、Eric Ferraris、Aaron Muzny、Shawn McAvoy、Christopher P. Miller、Keith A. Walters、Keith C. Russell、Evan Wang、Betsy Nuez、Carol Parish

  DOI：10.1021/jo7019724

  日期：2008.1.1

  [GRAPHICS]Three new isomeric dipyridoannulenes were synthesized and characterized. These molecules possess differing conjugation pathways between the substituent alkoxy donating groups and the pyridyl acceptor groups. Optical absorption and emission properties of the dipyridoannulenes and their corresponding acyclic precursors were measured and correlated to structural differences and used to evaluate conjugation effectiveness and charge-transfer pathways. Optical properties of protonated dipyridoannulenes were also measured and found to be somewhat insensitive to the degree of protonation. Density functional studies of these systems at the B3LYP/6-31G* level provided insight into their stabilities, polarities, and quinoidal character. An analysis of the HOMO and LUMO molecular orbitals provided further information regarding charge-transfer behavior. These systems are good metal binding candidates, as the pyridine moiety can act as both an electron-acceptor and a site for metal coordination.