1-[3-Tert-butyl-5-[4-(3-tert-butyl-5-ethynylphenyl)triazol-1-yl]phenyl]-4-(3-tert-butyl-5-ethynylphenyl)triazole | 1029002-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[3-Tert-butyl-5-[4-(3-tert-butyl-5-ethynylphenyl)triazol-1-yl]phenyl]-4-(3-tert-butyl-5-ethynylphenyl)triazole
• CAS: 1029002-31-0
• 化学式: C₃₈H₄₀N₆
• 分子量: 580.776
• InChiKey: YJJPYMLNZDMBFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diazido-1-(tert-butyl)benzene 、 1-[3-Tert-butyl-5-[4-(3-tert-butyl-5-ethynylphenyl)triazol-1-yl]phenyl]-4-(3-tert-butyl-5-ethynylphenyl)triazole 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以70%的产率得到8,17,26,35-Tetratert-butyl-2,3,4,12,13,14,20,21,22,30,31,32-dodecazanonacyclo[31.3.1.12,5.16,10.111,14.115,19.120,23.124,28.129,32]tetratetraconta-1(37),3,5(44),6(43),7,9,11(42),12,15(41),16,18,21,23(40),24,26,28(39),29(38),30,33,35-icosaene
  参考文献：
  名称：

  Strong, Size-Selective, and Electronically Tunable C−H···Halide Binding with Steric Control over Aggregation from Synthetically Modular, Shape-Persistent [3₄]Triazolophanes

  摘要：

  A series of shape-persistent [3(4)]triazolophanes bearing t-butyl or triethylene glycol (OTg) substituents on the phenylene linkers have been prepared in a modular manner from simple building blocks. Triazolophane-halide binding affinities were determined using UV titrations in order to help in understanding the driving forces behind the large receptor-anion binding strengths supported solely by CH hydrogen-bond donors. The fixed size of the central cavity provides a means for selective recognition of Cl- and Br- anions with large binding strengths (K-a > 1 000 000 M-1; Delta G > -8.5 kcal mol(-1)). The smaller F- and larger I- anions are bound less tightly by similar to 1 and similar to 3 orders of magnitude, respectively. The four triazole-based H-bond donors are believed to be of primary importance, while the four phenylene CH H-bond donors take on a secondary role. Consistent with this idea, the binding affinity can be tuned by as much as 1 kcal mol-1 by changing the character of the four phenylene-based substituents from more (OTg) to less (t-butyl) electron-donating. Preorganization was also found to play a central role, on the basis of comparisons with a foldamer analogue that shows much-reduced binding. Aggregation was facilitated as the substituents were changed from t-butyl to OTg, increasing the degree of self-association from K-E approximate to 0 to 230 M-1 in CD2Cl2. Diffusion NMR experiments established aggregation as opposed to dimerization. These findings indicate the importance of the cavity size for selective anion recognition as well as the role of the phenylene linkers in tuning the binding strengths and modulating the aggregation of the [3(4)]triazolophanes.

  DOI：

  10.1021/ja803341y
• 作为产物：
  描述：

  1-(tert-butyl)-3,5-diiodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 8.5h， 生成 1-[3-Tert-butyl-5-[4-(3-tert-butyl-5-ethynylphenyl)triazol-1-yl]phenyl]-4-(3-tert-butyl-5-ethynylphenyl)triazole
  参考文献：
  名称：

  芳族和脂肪族CH氢键争夺氯离子，同时与Triazolophanes内的离子配对竞争。

  摘要：

  三唑烷用作竞争脂肪族丙烯CH氢键供体与芳香亚苯基竞争的场所。更长的脂肪族的C  ħ ⋅⋅⋅氯-氢键从的基于丙烯的triazolophane内氯化物的位置计算。通过考虑所有低能构象，计算出氯离子结合的气相能（ΔG结合，ΔH结合，ΔS结合）和构型熵（ΔS config）。从Δ结合降低所计算的气相自由能的亚苯基和基于丙烯的triazolophanes节目之间的比较ģ绑定= -194到-182千焦摩尔-1，分别与适度的焓-比熵的补偿。对这些差异进行了实验研究。的1 H NMR光谱对丙烯triazolophane的结构研究的1：1个的氯化物络合物是用较弱的丙烯CH氢键相一致。为了量化在二氯甲烷两个triazolophanes之间的亲和力的差异，这是至关重要的，以获得准确的结合模型。确定了四个平衡点。除了1：1个复合及2:1夹心形成，所述四丁基氯化铵盐（TBA的离子配对+ ⋅氯- ）和阳离子配对的TBA

  DOI：

  10.1002/chem.201002340

文献信息

• Pure CH Hydrogen Bonding to Chloride Ions: A Preorganized and Rigid Macrocyclic Receptor
  作者：Yongjun Li、Amar H. Flood

  DOI：10.1002/anie.200704717

  日期：2008.3.25