(allyloxy)phenyldimethylsilane | 13360-20-8

• 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: (allyloxy)phenyldimethylsilane
• 英文别名: (allyloxy)dimethylphenylsilane；Dimethyl-phenyl-prop-2-enoxysilane
• CAS: 13360-20-8
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: UZAIMYWRLZVDEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  76-78 °C(Press: 9 Torr)
• 密度：
  0.9419 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (allyloxy)phenyldimethylsilane 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 scandium tris(trifluoromethanesulfonate) 、 三环己基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3S)-3-Cyclohexyl-3-methoxy-2-methyl-propionaldehyde
  参考文献：
  名称：

  醛与乙醛的立体选择性Sc（OTf）3-催化的醛基二取代的甲硅烷基烯醇醚的羟醛反应

  摘要：

  易于和模块化获得立体定义的二取代醛衍生的甲硅烷基烯醇醚，使其成功应用于立体选择性羟醛反应中，从而提供了具有优异收率和非对映体比率的产物。此Mukaiyama-aldol反应的违反直觉的立体化学行为是由非经典的开放过渡态引起的。

  DOI：

  10.1002/anie.202101634
• 作为产物：
  描述：

  二甲基苯基硅烷 、 烯丙醇 在 hydrido(triphenylphosphine)copper(I) hexamer air 作用下， 以 苯 为溶剂， 反应 4.0h， 以93%的产率得到(allyloxy)phenyldimethylsilane
  参考文献：
  名称：

  Lorenz, Catrin; Schubert, Ulrich, Chemische Berichte, 1995, vol. 128, # 12, p. 1267 - 1270

  摘要：

  DOI：

文献信息

• Rhodium Carbene Complexes as Versatile Catalyst Precursors for SiH Bond Activation
  作者：Anneke Krüger、Martin Albrecht

  DOI：10.1002/chem.201102197

  日期：2012.1.9

  Rhodium(III) complexes comprising monoanionic C,C,C‐tridentate dicarbene ligands activate SiH bonds and catalyse the hydrolysis of hydrosilanes to form silanols and siloxanes with concomitant release of H2. In dry MeNO2, selective formation of siloxanes takes place, while changing conditions to wet THF produces silanols exclusively. Silyl ethers are formed when ROH is used as substrate, thus providing

  包括单阴离子Ç铑（III）络合物，C，C-三齿配体dicarbene激活的Si  H键和催化氢硅烷的水解以形成硅烷醇和硅氧烷的H伴随释放2。在干燥的MeNO 2中，会选择性地形成硅氧烷，而改变条件以使湿THF专门产生硅烷醇。当将ROH用作底物时会形成甲硅烷基醚，因此为保护以H 2为唯一副产物的醇提供了一条温和的途径。对于炔烃，发生相当快速的氢化硅烷化，而羰基不受影响。Si的进一步扩展H键活化成二氢硅烷得到硅酮和聚甲硅烷基醚。使用氘代硅烷的机理研究表明氘掺入了异常的卡宾配体中，因此表明了涉及杂化SiH键裂解的配体辅助机制。
• Reduction of Allylpalladium(II)chloride Dimer by Formation of Allyloxy­silanes
  作者：Scott Denmark、Russell Smith

  DOI：10.1055/s-2006-951516

  日期：2006.11

  The reduction ofallylpalladium(II)chloride dimer (APC) to a Pd(0) species can be effected by reaction with alkali metal silanolates. The reduction is extremely rapid in the presence of chelating bisphosphine ligands and for a variety of silanolates.

  烯丙基氯化钯 (II) 二聚体 (APC) 还原为 Pd(0) 物质可以通过与碱金属硅烷醇盐反应来实现。在螯合双膦配体和各种硅烷醇化物存在的情况下，还原速度非常快。
• Direct transformation of allylic and benzylic alcohols or their silylated derivatives into organolithium compounds
  作者：Emma Alonso、David Guijarro、Miguel Yus

  DOI：10.1016/0040-4020(95)00709-h

  日期：1995.10

  The reaction of allylic or benzylic alcohols 1 with n-butyllithium followed by treatment with lithium powder and a catalytic amount of DTBB (5 mol %) in THF at room temperature gives a solution of the corresponding alkyllithium reagent, which reacts in situ with different electrophiles to yield the expected products 2. Alternatively, the O-silylated derivatives of the same alcohols are lithiated under Barbier-type reaction conditions to afford the same reaction products with better yields.
• An Efficient Solvent-Free Route to Silyl Esters and Silyl Ethers
  作者：Yuko Ojima、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1002/adsc.200900230

  日期：2009.6

  Abstractmagnified imageDinuclear metal complexes, especially (p‐cymene)ruthenium dichloride dimer [RuCl2(p‐cymene)]2}, have been found to exhibit high catalytic performance for the dehydrosilylation of various kinds of carboxylic acids and alcohols. The dehydrosilylation with [RuCl2(p‐cymene)]2 proceeded efficiently with only one equivalent of silane with respect to substrate (carboxylic acids or alcohols) under solvent‐free conditions to give the corresponding silyl esters and ethers in excellent yields with a high turnover number (TON) and frequency (TOF). The 1H NMR spectrum of a toluene‐d8 solution of [RuCl2(p‐cymene)]2 and a silane showed a signal assignable to the ruthenium hydride species. In contrast, no new signals were detected in the 1H NMR spectrum of a toluene‐d8 solution of [RuCl2(p‐cymene)]2 and a carboxylic acid or an alcohol. Therefore, the ruthenium metal in [RuCl2(p‐cymene)]2 activates a silane to afford the hydride intermediate, possibly a silylmetal hydride species. Then, the nucleophilic attack of a substrate (carboxylic acid or alcohol) to the hydride intermediate proceeds to give the corresponding silylated product. The present dehydrosilylation with an optically active silane proceeded exclusively under inversion of stereochemistry at the chiral silicon center, suggesting that the nucleophilic attack of a substrate to the hydride intermediate occurs from the backside of the ruthenium‐silicon bond.
• Zaslavskaya, T. N.; Reikhsfel'd, V. O.; Filippov, N. A., Journal of general chemistry of the USSR, 1980, vol. 50, # 11, p. 2001 - 2005
  作者：Zaslavskaya, T. N.、Reikhsfel'd, V. O.、Filippov, N. A.、Shornik, N. A.

  DOI：——

  日期：——