3-Trimethylsilyloxy-2,2-dimethyl-3-phenyl-propionsaeure-aethylester | 17875-59-1

• 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: 3-Trimethylsilyloxy-2,2-dimethyl-3-phenyl-propionsaeure-aethylester
• 英文别名: Ethyl 2,2-dimethyl-3-phenyl-3-trimethylsilyloxypropanoate
• CAS: 17875-59-1
• 化学式: C₁₆H₂₆O₃Si
• 分子量: 294.466
• InChiKey: LGDVLIONTWPHEI-UHFFFAOYSA-N

物化性质

• 沸点：
  81 °C(Press: 0.1 Torr)
• 密度：
  0.9804 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Trimethylsilyloxy-2,2-dimethyl-3-phenyl-propionsaeure-aethylester 在 盐酸 、 乙醇 作用下， 生成 ethyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate
  参考文献：
  名称：

  Birkofer,L. et al., Chemische Berichte, 1962, vol. 95, p. 971 - 976

  摘要：

  DOI：
• 作为产物：
  描述：

  bromozinc(1+);3-ethoxy-2,2-dimethyl-3-oxo-1-phenylpropan-1-olate 以87%的产率得到
  参考文献：
  名称：

  LAPKIN I. I.; CEMEHOB V. I.; SAJTKULOVA F. G., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1978, 21, HO 11, 1694-1696

  摘要：

  DOI：

文献信息

• Chemoselective aldol condensation in 5 mol dm−3 lithium perchlorate–nitromethane. A comparison with lithium perchlorate–diethyl ether medium
  作者：R. Sudha、S. Sankararaman

  DOI：10.1039/a900095j

  日期：——

  Aldol reactions of silyl enol ethers with aldehydes proceed in 5 mol dm–3 lithium perchlorate–nitromethane medium at ambient temperature. The reaction is highly chemoselective such that only aldehydes and cyclic ketones reacted while acyclic and aromatic ketones failed to react. The same reaction is not promoted in 5 mol dm–3 lithium perchlorate–diethyl ether medium. The difference between these two

  甲硅烷基烯醇醚与醛的醛醇缩合反应在环境温度为5 mol dm –3高氯酸锂–硝基甲烷的介质中进行。该反应是高度化学选择性的，使得仅醛和环状酮反应而无环和芳族酮不能反应。相同的反应不是在5摩尔分米促进-3的高氯酸锂-乙醚平台。两种介质之间的差异可通过与在乙醚中相比，在硝基甲烷中锂离子的路易斯酸酸度增加来解释。
• Aldol reactions, conjugate additions, and alkylation reactionsof O-silylated ketene acetals under neutral conditions
  作者：Yoshinori Yamamoto、Kazuhiro Maruyama、Kiyoshi Matsumoto

  DOI：10.1016/s0040-4039(01)80105-2

  日期：1984.1

  Aldol reactions, conjugate additions, and alkylation reactions of O-silylated ketene acetals take place under neutral conditions by using a high pressure technique.

  O-甲硅烷基化的乙烯酮缩醛的醛醇缩合反应，共轭加成和烷基化反应是在中性条件下通过高压技术进行的。
• Mukaiyama Aldol Reactions Catalyzed by Zirconocene Bis(triflate) Complexes:  Stereochemistry and Mechanisms for C−C Bond Formation
  作者：Shuqiong Lin、Georgiy V. Bondar、Christopher J. Levy、Scott Collins

  DOI：10.1021/jo971803g

  日期：1998.3.1

  The aldol condensations of alpha- and beta-(benzyloxy) aldehydes with enol silanes, catalyzed by Cp2Zr(OTf)(2) . THF or Cp2Zr(OTf)(2), in a variety of solvents were studied. The simple diastereoselectivity of these reactions is modest and comparable to that observed using simple aldehydes of similar steric requirements. Studies have revealed that TMSOTf is directly produced on reaction with the zirconocene catalyst with the enol silane in nitroalkane solvent or is formed during catalysis in dichloromethane solution. Although TMSOTf is known to catalyze cross-aldol reactions under these conditions, the rate of this process is not always competitive with that observed using the zircanocene catalysts. In particular, sterically unhindered or aromatic aldehydes react via a mechanism that appears to be mainly Zr-catalyzed, based on both the difference in rate between Zr- and Si-mediated reactions as well as differences in enol silane/silyl triflate reactivity in crossover-type experiments. With sterically hindered aldehydes in dichloromethane or nitromethane, catalysis is mediated by Si. The Zr-catalyzed process occurs via formation of a Zr-aldolate complex from aldehyde and enol silane, with liberation of TMSOTf, followed by rate-limiting O-silylatian of the metal aldolate by TMSOTf, as revealed by both model studies and in situ monitoring during catalysis.
• Parmee, Emma R.; Tempkin, Orin; Masamune, Satoru, Journal of the American Chemical Society, 1991, vol. 113, # 24, p. 9365 - 9366
  作者：Parmee, Emma R.、Tempkin, Orin、Masamune, Satoru、Abiko, Atsushi

  DOI：——

  日期：——
• Iron complexes as catalysts in aldol additions
  作者：Lino Colombo、Fausta Ulgheri、Laura Prati

  DOI：10.1016/s0040-4039(01)93915-2

  日期：1989.1