3-(二甲基硅烷基)吡啶 | 252974-70-2

• 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
• 中文名称: 3-(二甲基硅烷基)吡啶
• 英文名称: dimethyl(3-pyridyl)silane
• 英文别名: dimethyl(pyridin-3-yl)silane
• CAS: 252974-70-2
• 化学式: C₇H₁₁NSi
• 分子量: 137.257
• InChiKey: VJNQMPKFQBFCAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(二甲基硅烷基)吡啶 在 水 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到3-羟基吡啶
  参考文献：
  名称：

  芳基硅烷和芳基甲氧基硅烷的无氟氧化法合成苯酚

  摘要：

  已经开发了快速，有效的方法来由芳基氢硅烷的氧化制备苯酚。芳烃取代基和氟化助催化剂对这一过程的影响表明，尽管缺电子的芳烃可从氢硅烷中直接氧化，但富含电子的芳烃可通过使用均相或非均相过渡金属催化氧化为甲氧基硅烷而从硅烷活化中受益。还报道了将这两种氧化结合成流线型流程，该流程涉及对反应中间体的最少处理。

  DOI：

  10.1021/jo301363h
• 作为产物：
  描述：

  3-溴吡啶 、 二甲基一氯硅烷 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以78%的产率得到3-(二甲基硅烷基)吡啶
  参考文献：
  名称：

  使用二甲基（吡啶基）硅烷的烯烃和炔烃的金属催化氢化硅烷化。

  摘要：

  描述了使用二甲基（吡啶基）硅烷的烯烃和炔烃的金属催化的氢化硅烷化。使用二甲基（2-吡啶基）硅烷（2-PyMe（2）SiH）进行的烯烃氢化硅烷化在催化量的RhCl（PPh（3））（3）的存在下几乎完全区域选择性地进行得很好。通过利用2-PyMe（2）Si基团的相标签属性，通过简单的酸碱提取，氢化硅烷化产物的纯度大于95％。还证明了催化剂的战略性回收。使用2-PyMe（2）SiH的炔烃的氢化硅烷化与Pt（CH（2）= CHSiMe（2））（2）O / P（t-Bu）（3）催化剂进行，得到烯基二甲基（2-吡啶基）硅烷，产率高，区域选择性高。还进行了2-PyMe（2）SiH与其他相关的氢硅烷（3-PyMe（2）SiH，4-PyMe（2）SiH和PhMe（2）SiH）的反应性比较。在铑催化的反应中，氢硅烷的反应顺序为2-PyMe（2）SiH >> 3-PyMe（2）SiH，4-PyMe（2）SiH，

  DOI：

  10.1021/jo0163389

文献信息

• Oxidation of 2-Pyridyldimethylsilyl Group to Hydroxyl Group by H₂O₂/KF. Implication of Fluoride Ion Accelerated 2-Pyridyl−Silyl Bond Cleavage
  作者：Kenichiro Itami、Koichi Mitsudo、Jun-ichi Yoshida

  DOI：10.1021/jo990740u

  日期：1999.11.1
• 2-Pyridylsilyl group as a multifunctional “phase tag" for solution phase synthesis
  作者：Jun-ichi Yoshida、Kenichiro Itami、Koichi Mitsudo、Seiji Suga

  DOI：10.1016/s0040-4039(99)00474-8

  日期：1999.4

  2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective "phase: tag" for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2-PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utilitiy Of 2-PyMe2Si group as a "phase tag", a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.