2-[乙氧基(二甲基)甲硅烷基]丙酸乙酯 | 72227-79-3

• 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: 2-[乙氧基(二甲基)甲硅烷基]丙酸乙酯
• 英文名称: Ethyl 2-(ethoxydimethylsilyl)propionate
• 英文别名: Ethyl 2-[ethoxy(dimethyl)silyl]propanoate
• CAS: 72227-79-3
• 化学式: C₉H₂₀O₃Si
• 分子量: 204.341
• InChiKey: RXZATYJNUSLTHA-UHFFFAOYSA-N

物化性质

• 沸点：
  211.7±13.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醇 、 Diazo(trimethylsilyl)essigsaeure-methylester 生成 2-[乙氧基(二甲基)甲硅烷基]丙酸乙酯
  参考文献：
  名称：

  Photochemical decomposition of trimethylsilyl diazoacetates in alcohols

  摘要：

  DOI：

  10.1021/ja00515a038

文献信息

• Synthesis of α-(Alkoxysilyl)acetic esters. A route to 1,2 diols
  作者：Olivier Andrey、Yannick Landais、Denis Planchenault、Valéry Weber

  DOI：10.1016/0040-4020(95)00763-x

  日期：1995.10

  Si-H insertion of a carbenoid, generated by decomposition of N2CHCO2Et, followed by a nucleophilic attack onto the Si-Cl bond by an alcohol. Alkylation of the title esters, reduction of the ester function and finally oxidation of the C-Si bond provide a facile entry to 1,2-diols.

  描述了获得α-（烷氧基甲硅烷基）乙酸酯的简单方法及其应用。它涉及在一个罐中进行的两步序列：铑催化类固醇的Si-H插入，该分解是由N 2 CHCO 2 Et的分解产生的，然后是由醇对Si-Cl键的亲核攻击。标题酯的烷基化，酯官能度的降低以及最后C-Si键的氧化为1,2-二醇提供了便捷的入口。
• Highly regioselective carbonylation of vinylsilanes: a remarkable effect of organosilicon substituent
  作者：Ryo Takeuchi、Naomi Ishii、Nobuhiro Sato

  DOI：10.1039/c39910001247

  日期：——

  The Pd-catalysed hydroesterification of vinylsilanes affords β-silyl esters 1 in high yields with high selectivity, whereas α-silyl esters 2 are obtained in high yields with high selectivity by the Co catalyst.

  Pd 催化乙烯基硅烷的氢酯化反应以高产率和高选择性得到 β-甲硅烷基酯 1，而通过 Co 催化剂以高产率和高选择性获得 α-甲硅烷基酯 2。
• A one pot synthesis of α-(alkoxysilyl)acetic esters
  作者：Olivier Andrey、Yannick Landais、Denis Planchenault

  DOI：10.1016/s0040-4039(00)60483-5

  日期：1993.4

  An efficient synthesis of α-(alkoxysilyl)acetic esters by SiH insertion of carbenes, generated by rhodium catalysed decomposition of diazoacetic esters, followed by nucleophilic displacement of Cl by ROH has been developed. Alkylation of these α-silyl carbonyls followed by Tamao oxidation of the CSi bond allow an easy access to terminal diols.

  通过铑催化重氮乙酸酯的分解，然后通过ROH亲核取代Cl，可生成有效的合成方法，该方法是通过羧甲基的SiH插入生成羧甲基的SiH来高效合成α-（烷氧基甲硅烷基）乙酸酯。这些α-甲硅烷基羰基的烷基化，然后C TamSi键的Tamoo氧化使容易获得末端二醇。
• The highly regioselective carbonylation of vinylsilanes
  作者：Ryo Takeuchi、Naomi Ishii、Masaharu Sugiura、Nobuhiro Sato

  DOI：10.1021/jo00041a025

  日期：1992.7

  The hydroesterification of vinylsilanes, catalyzed by transition-metal complexes, afforded both beta-silyl esters 2 and alpha-silyl esters 3 in high yield. The Pd(II) complex-catalyzed reaction showed high beta-regioselectivity, whereas the Co2(CO)8-catalyzed reaction showed high alpha-regioselectivity. Vinylsilanes which bore trialkyl-, diphenylmethyl-, dimethylethoxy-, trimethoxy-, diphenylfluoro-, and difluorophenylsilyl groups were regioselectively, and some cases regiospecifically, hydroesterified. Pd(II) complexes were also shown to be effective catalysts of the hydrocarboxylation of vinylsilanes. Hydrocarboxylation was beta-regiospecific and gave excellent yields of beta-silyl carboxylic acids. Reasonable mechanisms for the reactions are described.
• Photochemical decomposition of trimethylsilyl diazoacetates in alcohols
  作者：Wataru Ando、Akira Sekiguchi、Tsuneo Hagiwara、Toshihiko Migita、Vinay Chowdhry、F. H. Westheimer、Seetha L. Kammula、Marilyn Green、Maitland Jones

  DOI：10.1021/ja00515a038

  日期：1979.10