3,11,19-Tri(pyrimidin-2-yl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-2,4,10,12,18,20-hexone | 1422526-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,11,19-Tri(pyrimidin-2-yl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-2,4,10,12,18,20-hexone
• 英文别名: 3,11,19-tri(pyrimidin-2-yl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-2,4,10,12,18,20-hexone
• CAS: 1422526-73-5
• 化学式: C₃₆H₂₁N₉O₆
• 分子量: 675.619
• InChiKey: ZXBCVPAQGFNKRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  51
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 间苯二甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以4%的产率得到3,11,19-Tri(pyrimidin-2-yl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-2,4,10,12,18,20-hexone
  参考文献：
  名称：

  Trezimides and Tennimides: New Imide-Based Macrocycles

  摘要：

  The reaction of isophthaloyl dichloride with 2-aminopyridine or 2-aminopyrimidine provides a facile entry into a new class of imide-based "3 + 3" macrocyclic trimer (trezimide), together with the known tetramer scaffold (tennimide). The trezimides can adopt two distinct asymmetric conformations in the solid state, isolated as (P) in (IO)(3) (from 2-aminopyridine) and (R) in (26IO)(3) (from 2-aminopyrimidine). The tennimide crystal structure (26IO)(4) (from 2-aminopyrimidine) exhibits three discrete conformational states, highlighting subtle geometric changes with the tennimide channel (pore) open (o) and/or closed (c), as noted by three macrocycle conformations with their channel pores observed as cc/oc/oo. Macrocycle formation (though in competition with oligomer/polymer formation) relies on the o-pyr(im)idine N functionality and preorganized imide hinge (the "CO center dot center dot center dot CO" twist) together with the inherent flexibility of the isophthaloyl groups.

  DOI：

  10.1021/jo302448h

文献信息

• Trezimides and Tennimides: New Imide-Based Macrocycles
  作者：Pavle Mocilac、John F. Gallagher

  DOI：10.1021/jo302448h

  日期：2013.3.15

  The reaction of isophthaloyl dichloride with 2-aminopyridine or 2-aminopyrimidine provides a facile entry into a new class of imide-based "3 + 3" macrocyclic trimer (trezimide), together with the known tetramer scaffold (tennimide). The trezimides can adopt two distinct asymmetric conformations in the solid state, isolated as (P) in (IO)(3) (from 2-aminopyridine) and (R) in (26IO)(3) (from 2-aminopyrimidine). The tennimide crystal structure (26IO)(4) (from 2-aminopyrimidine) exhibits three discrete conformational states, highlighting subtle geometric changes with the tennimide channel (pore) open (o) and/or closed (c), as noted by three macrocycle conformations with their channel pores observed as cc/oc/oo. Macrocycle formation (though in competition with oligomer/polymer formation) relies on the o-pyr(im)idine N functionality and preorganized imide hinge (the "CO center dot center dot center dot CO" twist) together with the inherent flexibility of the isophthaloyl groups.