1,4-bis(mesityl(1H-pyrrol-2-yl)methyl)benzene | 1186025-65-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4-bis(mesityl(1H-pyrrol-2-yl)methyl)benzene
• 英文别名: 1,4-bis((2,4,6-trimethylphenyl)(2-pyrrolyl)methyl)benzene；2-[[4-[1H-pyrrol-2-yl-(2,4,6-trimethylphenyl)methyl]phenyl]-(2,4,6-trimethylphenyl)methyl]-1H-pyrrole
• CAS: 1186025-65-9
• 化学式: C₃₄H₃₆N₂
• 分子量: 472.673
• InChiKey: NDFQNZVMRSGFGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-bis(mesityl(1H-pyrrol-2-yl)methyl)benzene 、 1,4-bis(mesitylhydroxymethyl)benzene 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以9.7 %的产率得到
  参考文献：
  名称：

  Breaking Global Diatropic Current to Tame Diradicaloid Character: Thiele's Hydrocarbon Under Macrocyclic Constraints

  摘要：

  A diradical/biradical character of organic derivatives is one of the key aspects of contemporary research focusing on the fundamental studies followed by potential applicability relying on the unique optical, electronic, or magnetic properties assigned to unpaired electrons. A precise involvement of two p‐phenylenes into a cyclophane‐like conjugated, diatropic system creates a flexible molecule with the two different characters of both subunits (benzene and quinone) imprinting into the structure a Kekulé delocalized system. A dynamic of both carbocyclic subunits, and their mutual interaction generates a singlet open‐shell state (J=−1.25 kcal/mol) as documented spectroscopically (NMR and EPR). The extended theoretical analysis has proved a correlation between dihedral angle and the diradicaloid character that shifts from a closed‐shell singlet to an open‐shell state, eventually showing the y₀=0.86 for 78 degrees and ΔE_ST=−0.34 kcal/mol.

  DOI：

  10.1002/anie.202400780
• 作为产物：
  描述：

  magnesium,1,3,5-trimethylbenzene-6-ide,bromide 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 1,4-bis(mesityl(1H-pyrrol-2-yl)methyl)benzene
  参考文献：
  名称：

  Breaking Global Diatropic Current to Tame Diradicaloid Character: Thiele's Hydrocarbon Under Macrocyclic Constraints

  摘要：

  A diradical/biradical character of organic derivatives is one of the key aspects of contemporary research focusing on the fundamental studies followed by potential applicability relying on the unique optical, electronic, or magnetic properties assigned to unpaired electrons. A precise involvement of two p‐phenylenes into a cyclophane‐like conjugated, diatropic system creates a flexible molecule with the two different characters of both subunits (benzene and quinone) imprinting into the structure a Kekulé delocalized system. A dynamic of both carbocyclic subunits, and their mutual interaction generates a singlet open‐shell state (J=−1.25 kcal/mol) as documented spectroscopically (NMR and EPR). The extended theoretical analysis has proved a correlation between dihedral angle and the diradicaloid character that shifts from a closed‐shell singlet to an open‐shell state, eventually showing the y₀=0.86 for 78 degrees and ΔE_ST=−0.34 kcal/mol.

  DOI：

  10.1002/anie.202400780

文献信息

• Steric Control in the Synthesis of <i>p</i>-Benziporphyrins. Formation of a Doubly N-Confused Benzihexaphyrin Macrocycle
  作者：Marcin Stȩpień、Bartosz Szyszko、Lechosław Latos-Grażyński

  DOI：10.1021/ol9016222

  日期：2009.9.3

  The use of 1,4-phenylene-containing tripyrrane analogs provides a general route to expanded p-benziporphyrins. The course of macrocyclization shows a striking dependence on the steric bulk of meso substituents.

  含1，4-亚苯基的三吡喃类似物的使用提供了扩展对-苯并卟啉的一般途径。大环化的过程显示出对内消旋取代基的空间体积的显着依赖性。
• Breaking Global Diatropic Current to Tame Diradicaloid Character: Thiele's Hydrocarbon Under Macrocyclic Constraints
  作者：Piotr Banachowicz、Mainak Das、Krzysztof Kruczała、Miłosz Siczek、Zbigniew Sojka、Monika Kijewska、Miłosz Pawlicki

  DOI：10.1002/anie.202400780

  日期：2024.4.22

  A diradical/biradical character of organic derivatives is one of the key aspects of contemporary research focusing on the fundamental studies followed by potential applicability relying on the unique optical, electronic, or magnetic properties assigned to unpaired electrons. A precise involvement of two p‐phenylenes into a cyclophane‐like conjugated, diatropic system creates a flexible molecule with the two different characters of both subunits (benzene and quinone) imprinting into the structure a Kekulé delocalized system. A dynamic of both carbocyclic subunits, and their mutual interaction generates a singlet open‐shell state (J=−1.25 kcal/mol) as documented spectroscopically (NMR and EPR). The extended theoretical analysis has proved a correlation between dihedral angle and the diradicaloid character that shifts from a closed‐shell singlet to an open‐shell state, eventually showing the y₀=0.86 for 78 degrees and ΔE_ST=−0.34 kcal/mol.