1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane
• 英文别名: 1,3-bis(3-pyridyl)tetramethyldisiloxane；1,1,3,3-Tetramethyl-1,3-bis(pyridin-3-yl)disiloxane；[dimethyl(pyridin-3-yl)silyl]oxy-dimethyl-pyridin-3-ylsilane
• 化学式: C₁₄H₂₀N₂OSi₂
• 分子量: 288.497
• InChiKey: WEFXAFIZFZVEKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl-1-oxide)disiloxane
  参考文献：
  名称：

  Synthesis and characterization of pyridinyldisiloxanes and their bis-N-oxides

  摘要：

  DOI：

  10.1016/0022-328x(87)87005-5
• 作为产物：
  描述：

  3-pyridyldimethylsilanol 反应 1.0h， 以36%的产率得到1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane
  参考文献：
  名称：

  Bis(pyridyl)siloxane Oligomeric Ligands for Palladium(II) Acetate: Synthesis and Binding Properties

  摘要：

  The complexation of a series of new bis(meia-pyridyl)methylsiloxane ligands with palladium(II) acetate in dilute toluene-d(8) solution was studied by (1)H NMR at 233-363 K, measuring the binding affinity and ring chain distribution as a function of ligand structure, temperature, and concentration. Significant differences in the ring distribution and Pd binding affinity were observed as a function of siloxane chain length, with hexa- and heptasiloxane spacers binding Pd most effectively. The (1)H NMR resonance of the singlet ortho aromatic proton was shifted unusually far downfield for the bidentate complex; the effect was strongest for the shortest chains and disappeared for chains with 10 or more siloxane units. Fitting the experimental data to a modified Jacobson-Stockmayer model demonstrated that the bidentate bis(pyridyl)siloxane complexes function as chelates in the concentration range 1-10 mM. Variable-temperature studies showed that all of the observed cyclic coordination oligomers are strainless. Therefore, entropic effects are implicated as the main cause of the observed trends in binding affinity, particularly the loss of conformational freedom of the siloxane chain upon binding.

  DOI：

  10.1021/om100316n
• 作为试剂：
  描述：

  碘苯 、 木榴油 在 copper(l) iodide 、 potassium carbonate 、 1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以61%的产率得到2-甲氧基苯基苯醚
  参考文献：
  名称：

  铜 (I)/吡啶官能化硅烷催化乌尔曼二芳基醚合成

  摘要：

  图形摘要 摘要 Ullmann 型二芳基醚合成在温和条件下在 DMF/K2CO3 中使用吡啶官能化硅烷作为配体进行。以良好的收率获得了产物。该方法耐受多种官能团，在受阻二芳基醚和杂芳基醚的合成中有效。

  DOI：

  10.1080/10426507.2015.1119135

文献信息

• Silanes
  申请人：Indiana University Foundation

  公开号：US04855433A1

  公开（公告）日：1989-08-08

  Novel silylpyridine monomers and dimers and their N-oxide derivatives and poly(methylpyridinylsiloxane) polymers and copolymers and their N-oxide derivatives have utility as inverse phase transfer catalysts.

  新型硅基吡啶单体和二聚体及其N-氧化物衍生物以及聚(甲基吡啶基硅氧烷)聚合物和共聚物及其N-氧化物衍生物在反相转移催化剂中具有实用性。
• Unusual anion effects on the solution-behavior of cyclodimeric Pd(II) complex
  作者：Yoon Kyong Ryu、Cho Rong Kim、Tae Hwan Noh、Jae Kyun Lee、Ok-Sang Jung

  DOI：10.1016/j.molstruc.2009.08.033

  日期：2009.12

  Unusual anion effects on the solution-behavior of [(dppp)Pd(m-ptms)](2)(X)(4) (dppp = 1,3-bis(diphenylphosphino)propane; m-ptms = 1,3-bis(3-pyridyl)tetramethyldisiloxane; X = CF3SO3-, PF6-, ClO4-, and NO3-). based on the H-1 NMR chemical shifts and conductivity, were observed. The fluxionality of the cyclodimeric skeleton was found to be sensitive to the Hoffmeister series of anions. (C) 2009 Elsevier B.V. All rights reserved.
• ZELDIN, MARTEL
  作者：ZELDIN, MARTEL

  DOI：——

  日期：——
• ZELDIN M.; XU JIAN-MIN; TIAN CHENG-XIANG, J. ORGANOMET. CHEM., 326,(1987) N 3, 341-346
  作者：ZELDIN M.、 XU JIAN-MIN、 TIAN CHENG-XIANG

  DOI：——

  日期：——
• Bis(pyridyl)siloxane Oligomeric Ligands for Palladium(II) Acetate: Synthesis and Binding Properties
  作者：Michael N. Missaghi、John M. Galloway、Harold H. Kung

  DOI：10.1021/om100316n

  日期：2010.9.13

  The complexation of a series of new bis(meia-pyridyl)methylsiloxane ligands with palladium(II) acetate in dilute toluene-d(8) solution was studied by (1)H NMR at 233-363 K, measuring the binding affinity and ring chain distribution as a function of ligand structure, temperature, and concentration. Significant differences in the ring distribution and Pd binding affinity were observed as a function of siloxane chain length, with hexa- and heptasiloxane spacers binding Pd most effectively. The (1)H NMR resonance of the singlet ortho aromatic proton was shifted unusually far downfield for the bidentate complex; the effect was strongest for the shortest chains and disappeared for chains with 10 or more siloxane units. Fitting the experimental data to a modified Jacobson-Stockmayer model demonstrated that the bidentate bis(pyridyl)siloxane complexes function as chelates in the concentration range 1-10 mM. Variable-temperature studies showed that all of the observed cyclic coordination oligomers are strainless. Therefore, entropic effects are implicated as the main cause of the observed trends in binding affinity, particularly the loss of conformational freedom of the siloxane chain upon binding.