2-[(三甲基硅烷基)甲基]-丙二酸二乙酯 | 17962-38-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-[(三甲基硅烷基)甲基]-丙二酸二乙酯
• 中文别名: 2-[(三甲基硅基)甲基]丙二酸乙酯
• 英文名称: diethyl<(trimethylsilyl)methyl>malonate
• 英文别名: diethyl 2-((trimethylsilyl)methyl)malonate；diethyl trimethylsilylcarboxylic acid；diethyl trimethylsilylmethylmalonate；me3Si{et-2-(COOet)2}；trimethylsilanylmethyl-malonic acid diethyl ester；Trimethylsilylmethyl-malonsaeure-diaethylester；Propanedioic acid, [(trimethylsilyl)methyl]-, diethyl ester；diethyl 2-(trimethylsilylmethyl)propanedioate
• CAS: 17962-38-8
• 化学式: C₁₁H₂₂O₄Si
• 分子量: 246.379
• InChiKey: ZEOGFXACYDZIKN-UHFFFAOYSA-N

物化性质

• 沸点：
  119°C 13mm
• 密度：
  0,969 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  2-[(三甲基硅烷基)甲基]-丙二酸二乙酯 在 氢氧化钾 作用下， 生成 3-三甲基硅基丙酸
  参考文献：
  名称：

  Synthesis and investigation of the dipole moments of ?-(n-alkyldimethylsilyl)propionic acids

  摘要：

  DOI：

  10.1007/bf00947552
• 作为产物：
  描述：

  sodium diethylmalonate 、 氯甲基三甲基硅烷 以 not given 为溶剂， 生成 2-[(三甲基硅烷基)甲基]-丙二酸二乙酯
  参考文献：
  名称：

  Organosilicon acids

  摘要：

  公开号：

  US02589445A1

文献信息

• A NOVEL SYNTHESIS OF TERMINAL OLEFINS BY ANODIC OXIDATION OF CARBOXYLIC ACIDS HAVING A TRIMETHYLSILYL GROUP ON THE β-POSITION
  作者：Tatsuya Shono、Hiroshi Ohmizu、Naoki Kise

  DOI：10.1246/cl.1980.1517

  日期：1980.12.5

  Anodic oxidation of carboxylic acids having a trimethylsilyl group on the β-position gave exclusively terminal olefins in reasonable yields.

  在β-位具有三甲基甲硅烷基的羧酸的阳极氧化以合理的产率仅产生端烯烃。
• Synthesis of rac-2′-(trimethylsilyl)isovaline: A novel silicon-containing α,α-dialkylated α-amino acid
  作者：Steffen Falgner、Ginka Buchner、Reinhold Tacke

  DOI：10.1016/j.jorganchem.2010.08.027

  日期：2010.11

  An efficient, convenient, and reliable multi-step synthesis of rac-2′-(trimethylsilyl)isovaline (rac-3) that uses inexpensive reagents in all steps has been developed, starting from diethyl malonate (overall yield 28%). Compound rac-3 is the first α-ethylated α,α-dialkylated silicon-containing α-amino acid.

  从丙二酸二乙酯（总收率28％）开始，开发了一种在所有步骤中均使用廉价试剂的rac -2'-（三甲基甲硅烷基）异戊酸（rac - 3）的高效，便捷和可靠的多步合成方法。化合物rac - 3是第一个α-乙基化的α，α-二烷基化的含硅的α-氨基酸。
• Palladium-catalyzed trimethylenemethane reaction to form methylenetetrahydrofurans. Reactions of substituted TMM precursors and mechanistic interpretation
  作者：Barry M. Trost、Steven A. King

  DOI：10.1021/ja00157a061

  日期：1990.1
• 2-Alkoxycarbonylallyltrimethylsilanes as new reagents of 2-alkoxycarbonylallylation of electrophiles
  作者：Akira Hosomi、Hidehiko Hashimoto、Hideki Sakurai

  DOI：10.1016/s0040-4039(00)77748-3

  日期：1980.1
• β-Silyl Effects on the Stabilities of Carbanions and Carbon-Centered Radicals Derived from Ethyl Thionacetates, Diethyl Malonates, and Ethyl Acetoacetates
  作者：Shizhong Zhang、Frederick G. Bordwell

  DOI：10.1021/jo951506g

  日期：1996.1.1

  The effects of an alpha-Me(3)SiCH(2) group on the equilibrium acidities in DMSO of the acidic C-H bonds in esters, including ethyl thionacetate, diethyl malonate, and ethyl acetoacetate, were found to differ from that of an alpha-MeCH(2) group by less than 1 kcal/mol, pointing to little or no stabilizing effect of a beta-Me(3)Si group on carbanion stabilities. On the other hand, substitution of an alpha-Me(3)SiCH(2) group for one of the acidic hydrogen atoms in these esters to give Me(3)SiCH(2)CH(2)C(=S)OEt, Me(3)SiCH(2)CH(CO(2)Et)(2), and Me(3)SiCH(2)CH(CO(2)Et)COCH3 was found to decrease the homolytic bond dissociation energies (BDEs) of the remaining acidic C-H bonds by 7.1, 8.2, and 7.1 kcal/mol, respectively, relative to those of the parent esters and by 2.7, 4.5, and 4.4 kcal/mol, respectively, relative to the BDEs of the acidic C-H bonds in the corresponding MeCH(2)-substituted esters. The differences in BDEs observed between the Me(3)SiCH(2)- and the MeCH(2)-substituted ester derivatives are indicative of the presence of 3-5 kcal/mol C-H bond stabilizing effects of beta-Me(3)Si groups, relative to those of beta-Me groups, on the corresponding carbon radicals. The BDE value of the acidic C-H bond in Me3(C)CH(2)CH(2)C(=S)OEt was found to be 86.4 kcal/mol, which represents a 0.6 kcal/mol increase in BDE relative to that of the acidic C-H bond in MeCH(2)CH(2)C(=S)OEt. This result demonstrates the absence of a stabilizing effect of a beta-tert-butyl group on an open-chain carbon-centered radical. This is contrary to an apparent 6.4 kcal/mol C-H bond stabilizing effect of the beta-tert-butyl group in 9-neopentylfluorene, relative to that in fluorene, which is attributed to the relief of steric strain in forming the radical.