3-iodo-1-tert-butyl-5-(trimethylsilylethynyl)benzene | 184349-51-7

• 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-iodo-1-tert-butyl-5-(trimethylsilylethynyl)benzene
• 英文别名: 2-(3-Tert-butyl-5-iodophenyl)ethynyl-trimethylsilane
• CAS: 184349-51-7
• 化学式: C₁₅H₂₁ISi
• 分子量: 356.322
• InChiKey: ZDFXZZAVEJGCMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-iodo-1-tert-butyl-5-(trimethylsilylethynyl)benzene 在 potassium fluoride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 3-iodo-5-ethynyl-1-tert-butylbenzene
  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 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以62%的产率得到3-iodo-1-tert-butyl-5-(trimethylsilylethynyl)benzene
  参考文献：
  名称：

  纯CH氢键与氯离子的键合：一种预先组织好的刚性大环受体。

  摘要：

  DOI：

  10.1002/anie.200704717

文献信息

• Solid-Phase Synthesis of Phenylacetylene Oligomers Utilizing a Novel 3-Propyl-3-(benzyl-supported) Triazene Linkage
  作者：James C. Nelson、James K. Young、Jeffrey S. Moore

  DOI：10.1021/jo961250u

  日期：1996.11.15

  Sequence-specific phenylacetylene oligomers consisting of functionalized monomers (hexyl benzoate, hexyl phenyl ether, benzonitrile, and tert-butylphenyl) are synthesized in gram quantities using solid-phase methods. Growing oligomers are attached to a divinylbenzene cross-linked polystyrene support by the 1-aryl-3-propyl-3-(benzyl-supported) triazene moiety. This linkage is obtained by reaction of arenediazonium tetrafluoroborate salts with a n-propylamino-modified Merrifield resin. Condensation strategies are described, producing oligomers with higher yields and simplified procedures compared to solution-phase methods. Terminal acetylene is protected with a trimethylsilyl group. After deprotection of the resin-bound terminal acetylene, an aryl iodide monomer or an aryl iodide-terminated oligomer is coupled to the supported oligomer using a palladium(0) catalyst. The cycle can be repeated to produce sequence-specific oligomers of varying length and functionality. The resulting oligomers are liberated from the polymer support by cleavage of the 1-aryl-3-propyl-3-(benzyl-supported) triazene group by reaction with iodomethane producing an aryl iodide.