3-(3-(dimethyl(phenyl)silyl)-3-phenylpropanoyl)oxazolidin-2-one | 1039768-44-9

• 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: 3-(3-(dimethyl(phenyl)silyl)-3-phenylpropanoyl)oxazolidin-2-one
• 英文别名: (S)-3-(1-oxo-3-dimethylphenylsilyl-3-phenylpropyl)-2-oxazolidinone；3-[(3S)-3-[dimethyl(phenyl)silyl]-3-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 1039768-44-9
• 化学式: C₂₀H₂₃NO₃Si
• 分子量: 353.493
• InChiKey: ZNAOXVHSPVBEJV-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-3-(1-oxo-3-phenyl-2-propen-1-yl)-2-oxazolidinone 、 (二甲基苯硅烷基)硼酸频那醇酯 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 水 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以60%的产率得到3-(3-(dimethyl(phenyl)silyl)-3-phenylpropanoyl)oxazolidin-2-one
  参考文献：
  名称：

  铑（I）催化亲核硅的1,4-加成

  摘要：

  铑（I）催化的硅-硼键活化，即通过Rh I -OH络合物将硅从硼转变为铑（I），可以将亲核硅共轭转移到α，β上-不饱和受体。预制的或原位形成的阳离子铑（I）-联萘酚配合物可催化这种新型的碳-硅键形成，具有出色的对映体控制能力，环状羰基和羧基化合物的ee为92％至> 99％ee，无环羧基化合物的ee> 99％。

  DOI：

  10.1016/j.tet.2009.01.111

文献信息

• An Insoluble Copper(II) Acetylacetonate–Chiral Bipyridine Complex that Catalyzes Asymmetric Silyl Conjugate Addition in Water
  作者：Taku Kitanosono、Lei Zhu、Chang Liu、Pengyu Xu、Shu̅ Kobayashi

  DOI：10.1021/jacs.5b11418

  日期：2015.12.16

  Acicular purplish crystals were obtained from Cu(acac)(2) and a chiral bipyridine ligand. Although the crystals were not soluble, they nevertheless catalyzed asymmetric silyl conjugate addition of lip ophilic substrates in water. Indeed, the reactions proceeded efficiently only in water; they did not proceed well either in organic solvents or in mixed water/organic solvents in which the catalyst/substrates were soluble. This is in pronounced contrast to conventional organic reactions wherein the catalyst/substrates tend to be in solution. Several advantages of the chiral Cu(II) catalysis in water over previously reported catalyst systems have been demonstrated. Water is expected to play a prominent role in constructing and stabilizing sterically confined transition states and accelerating subsequent protonation to achieve high yields and enantioselectivities.
• Catalytic Asymmetric CSi Bond Formation to Acyclic α,β-Unsaturated Acceptors by RhI-Catalyzed Conjugate Silyl Transfer Using a SiB Linkage
  作者：Christian Walter、Martin Oestreich

  DOI：10.1002/anie.200800361

  日期：2008.5.5