(4-methylbenzyloxy)dimethylphenylsilane | 58864-00-9

• 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: (4-methylbenzyloxy)dimethylphenylsilane
• 英文别名: Dimethyl-[(4-methylphenyl)methoxy]-phenylsilane
• CAS: 58864-00-9
• 化学式: C₁₆H₂₀OSi
• 分子量: 256.42
• InChiKey: LUYVOKOHWRCSIM-UHFFFAOYSA-N

物化性质

• 沸点：
  337.5±21.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二甲基苯基硅烷 、 对甲基苯甲醛 在 2,6-二甲基吡啶 、 C₂₆H₂₀P⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以89%的产率得到(4-methylbenzyloxy)dimethylphenylsilane
  参考文献：
  名称：

  磷鎓离子作为掩蔽鏻催化剂：机理评价和在合成中的应用

  摘要：

  介绍了磷鎓离子的利用；描述了优化和加宽的三元环结构以及将这些离子用作使用硅烷进行无金属羰基还原的有效预催化剂。介绍了鏻离子的完整表征，初步的实验和计算机制研究表明，它们充当“掩蔽鏻”源，可通过开环访问。催化通过 {Ph 2 P + } 的缔合转移到羰基亲核试剂 H–SiR 3 进行C=O 基团上的键加成，以及产物被进一步当量的羰基底物的缔合置换，从而完成催化循环。详细介绍了导致乙烯基膦形成的竞争性停循环过程，用于二苯甲酮的氢化硅烷化，在 [硅烷] 中观察到相反的顺序。实验上，副产物（包括非循环乙烯基膦）的形成有利于鏻阳离子上的给电子取代基，而吸电子取代基促进催化氢化硅烷化。这些观察结果在并行计算研究中得到了合理化。

  DOI：

  10.1021/acscatal.1c01133

文献信息

• Efficient carbon-supported heterogeneous molybdenum-dioxo catalyst for chemoselective reductive carbonyl coupling
  作者：Shengsi Liu、Jiaqi Li、Titel Jurca、Peter C. Stair、Tracy L. Lohr、Tobin J. Marks

  DOI：10.1039/c7cy00336f

  日期：——

  Reductive coupling of various carbonyl compounds to the corresponding symmetric ethers with dimethylphenylsilane is reported using a carbon-supported dioxo-molybdenum catalyst. The catalyst is air- and mositure-stable and can be easily separated from the reaction mixture for recycling. In addition, the catalyst is chemoselective, thus enabling the synthesis of functionallized ethers without requiring

  据报道，使用碳负载的二氧钼钼催化剂可将各种羰基化合物与二甲基苯基硅烷还原偶联至相应的对称醚上。该催化剂是空气和水分稳定的，并且可以容易地从反应混合物中分离出来以进行再循环。另外，该催化剂是化学选择性的，因此能够合成官能化的醚而无需牺牲性配体或保护基团。
• Bideau, Franck Le; Coradin, Thibaud; Henique, Josette, Chemical Communications, 2001, # 15, p. 1408 - 1409
  作者：Bideau, Franck Le、Coradin, Thibaud、Henique, Josette、Samuel, Edmond

  DOI：——

  日期：——
• Efficient hydrosilylation of carbonyl compounds by 1,1,3,3-tetramethyldisiloxane catalyzed by Au/TiO2
  作者：Eleni Vasilikogiannaki、Ioannis Titilas、Charis Gryparis、Anastasia Louka、Ioannis N. Lykakis、Manolis Stratakis

  DOI：10.1016/j.tet.2014.03.094

  日期：2014.9

  1,1,3,3-Tetramethyldisiloxane (TMDS) is a highly reactive reducing reagent in the Au/TiO2-catalyzed hydrosilylation of carbonyl compounds relative to monohydrosilanes. The reduction of aldehydes or ketones with TMDS can be performed on many occasions at ambient conditions within short reaction times and at low loading levels of gold, whereas typical monohydrosilanes require excess heating and prolonged time for completion. The product yields are excellent, while almost stoichiometric amounts of carbonyl compounds and TMDS can be used. It is postulated that the enhanced reactivity of TMDS is attributed to the formation of a gold dihydride intermediate. This intermediate is also supported by the fact that double hydrosilylation of carbonyl compounds by TMDS is a negligible pathway. (C) 2014 Elsevier Ltd. All rights reserved.
• Role of Low-Valent Rhenium Species in Catalytic Hydrosilylation Reactions with Oxorhenium Catalysts
  作者：Jessica L. Smeltz、Paul D. Boyle、Elon A. Ison

  DOI：10.1021/om300654q

  日期：2012.9.10

  The catalytic competency of a Re(III) complex has been demonstrated. In the presence of silane, oxorhenium(V) catalysts are deoxygenated to produce species that are significantly more active than the metal oxo precursors in hydrosilylation reactions. The results presented suggest that, in evaluating mechanisms for catalytic hydrosilylation reactions that involve high-valent metal oxo complexes, the activity of species that may be generated by deoxygenation of the metal with silane should also be systematically investigated as potential catalysts.