3,5-diazido-1-(tert-butyl)benzene | 1029002-25-2

• 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: 3,5-diazido-1-(tert-butyl)benzene
• 英文别名: 3,5-diazido-1-tert-butylbenzene；3,5-diazido-1-tertbutylbenzene；1,3-Diazido-5-tert-butylbenzene；1,3-diazido-5-tert-butylbenzene
• CAS: 1029002-25-2
• 化学式: C₁₀H₁₂N₆
• 分子量: 216.245
• InChiKey: UEVAIBRXNKZSLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.7
• 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 、 (碘乙炔基)苯 在 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到1,1'-(5-tert-butyl-1,3-phenylene)bis(5-iodo-4-phenyl-1H-1,2,3-triazole)
  参考文献：
  名称：

  Multifunctional Deuterated and Tritiated ‘Click’ Molecular Probes via ­Palladium-Mediated Reductive Deiodination of 5-Iodo-1,2,3-Triazoles

  摘要：

  Tritiated compounds are invaluable tools for in vitro and in vivo studies on bioactive molecules. Here we describe a click-chemistry'-based strategy for deuteration and tritiation of multifunctional compounds and multimodal molecular imaging probes. The method relies on a palladium-mediated reductive deiodination of 5-iodo-1,2,3-triazoles in the presence of NaBD4, deuterium or tritium gas.

  DOI：

  10.1055/s-0033-1340940
• 作为产物：
  描述：

  1-(tert-butyl)-3,5-diiodobenzene 在 copper(l) iodide 、 sodium azide 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以96%的产率得到3,5-diazido-1-(tert-butyl)benzene
  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

• Light Propagation in High-Spin Organic Microtubes Self-Assembled from Shape Persistent Macrocycles Carrying Oxo-Verdazyl Biradicals
  作者：Pramiti Hui、Rajadurai Chandrasekar

  DOI：10.1002/adma.201300540

  日期：2013.6.4

  A 1D paramagnetic organic tube self‐assembled from a “clicked” shape‐persistent macrocycle carrying high‐spin oxoverdazyl biradicals shows optical wave guiding behavior.

  一维顺磁有机管是由“点击”形状持久大环自组装而成，并带有高自旋的氧杂二氮杂双自由基，显示出光波导的行为。
• Strong, Size-Selective, and Electronically Tunable C−H···Halide Binding with Steric Control over Aggregation from Synthetically Modular, Shape-Persistent [3_<i>4</i>]Triazolophanes
  作者：Yongjun Li、Amar H. Flood

  DOI：10.1021/ja803341y

  日期：2008.9.10

  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.
• 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
• ‘Cleft-form’ electrochemical anion chemosensor with amide and triazole donor groups
  作者：Qian-Yong Cao、Tuhin Pradhan、Min Hee Lee、Dong Hoon Choi、Jong Seung Kim

  DOI：10.1016/j.tetlet.2012.06.118

  日期：2012.9

  A novel 'cleft-form' electrochemical anion receptor bearing amide and triazole donor groups, 1, has been synthesized and characterized. Among various anions, 1 shows a significant anodic shift response for H2PO4- and F-, with its multiple N-H center dot center dot center dot anion and C-H center dot center dot center dot anion interactions, which is supported by theoretical calculation and NMR titration results. (C) 2012 Elsevier Ltd. All rights reserved.
• A Pyrrolyl-Based Triazolophane: A Macrocyclic Receptor With CH and NH Donor Groups That Exhibits a Preference for Pyrophosphate Anions
  作者：Jonathan L. Sessler、Jiajia Cai、Han-Yuan Gong、Xiaoping Yang、Jonathan F. Arambula、Benjamin P. Hay

  DOI：10.1021/ja107098r

  日期：2010.10.13

  A pyrrolyl-based triazolophane, incorporating CH and NH donor groups, acts as a receptor for the pyrophosphate anion in chloroform solution. It shows selectivity for this trianion, followed by HSO4- > H2PO4- > Cl- > Br- (all as the corresponding tetrabutylammonium salts), with NH-anion interactions being more important than CH-anion interactions. In the solid state, the receptor binds the pyrophosphate anion in a clip-like slot via NH and CH hydrogen bonds.