二甲基苯基甲硅烷基乙酸 | 17887-62-6

• 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: 二甲基苯基甲硅烷基乙酸
• 英文名称: (dimethylphenylsilyl)acetic acid
• 英文别名: dimethylphenylsilyl acetic acid；dimethylphenylsilylacetic acid；me2(me-cox)Siph；(dimethyl-phenyl-silanyl)-acetic acid；(Dimethyl-phenyl-silyl)-essigsaeure；2-[dimethyl(phenyl)silyl]acetic acid
• CAS: 17887-62-6
• 化学式: C₁₀H₁₄O₂Si
• mdl: MFCD01862810
• 分子量: 194.305
• InChiKey: AZXBEYAODSEDFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  二甲基苯基甲硅烷基乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 生成 (dimethylphenylsilyl)ketene
  参考文献：
  名称：

  Kostyuk,A.S. et al., Journal of general chemistry of the USSR, 1979, vol. 49, p. 1346 - 1353

  摘要：

  DOI：
• 作为产物：
  描述：

  (dimethylphenylsilyl)ketene 在 水 作用下， 以 氘代乙腈 为溶剂， 反应 14.0h， 生成 二甲基苯基甲硅烷基乙酸
  参考文献：
  名称：

  Phenyldimethylsilyl-Substituted Ketenes and Bisketenes

  摘要：

  The phenyldimethylsilyl-substituted monoketene PhMe(2)SiCH=C=O (1) and bisketene (PhMe(2)SiC=C=O)(2) (3) have been prepared and compared to the corresponding Me(3)Si- and t-BuMe(2)Si-substituted species. The C-13, O-17, and Si-29 NMR spectra fit the pattern shown by other silylketenes and provide no evidence for transmission of a substituent effect of the Ph group through the silicon to the ketenyl group, as has been proposed for PhMe(2)Si-substituted radicals. The UV spectrum of 1 does show a longer lambda and greater epsilon than for t-BuMe(2)SiCH=C=O, and this may indicate some interaction of the phenyl group with the ketene chromophore, while the greater reactivity of 1 in hydration compared to t-BuMe(2)SiCH=C=O is ascribed to the inductive effect of the phenyl. The very similar ring-opening reactivity of the bis(phenyldimethylsilyl)cyclobutenedione (6) to form 3 compared to the bis(Me(3)Si) analogues also provides no evidence of a significant interaction of the phenyl with the ketene. A new type of stabilized 1,8-bisketene based on the arylbis(dimethylsilyl) grouping, namely, 1,4-bis(ketenyldimethylsilyl)benzene (12), has been prepared for the first time.

  DOI：

  10.1021/jo9605197

文献信息

• A Desilylative Approach to Alkyl Substituted C(1)‐Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions
  作者：Yihong Wang、Claire M. Young、Honglei Liu、Will C. Hartley、Max Wienhold、David. B. Cordes、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1002/anie.202208800

  日期：2022.9.19

  The catalytic generation of unsubstituted and alkyl substituted C(1)-ammonium enolates from α-silyl-α-alkyl substituted carboxylic acids using the isothiourea HyperBTM has been developed and applied in enantioselective [2+2]-cycloaddition reactions.

  使用异硫脲 HyperBTM 从 α-甲硅烷基-α-烷基取代的羧酸催化生成未取代和烷基取代的 C(1)-烯醇化铵已被开发并应用于对映选择性 [2+2]-环加成反应。
• Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones
  作者：Yihong Wang、Claire M. Young、David B. Cordes、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/acs.joc.2c02688

  日期：2023.6.16

  on both reaction components. Solely [2 + 2] cycloaddition products are observed when using α,β-substituted trifluoromethylenones or α-trialkylsilyl acetic acid derivatives; both [2 + 2] and [4 + 2] cycloaddition products are observed when using β-substituted trifluoromethylenones and α-alkyl-α-trialkylsilyl acetic acids as reactants, with the [2 + 2] cycloaddition as the major reaction product. The beneficial

  已开发出异硫脲催化的 C(1)-烷基和 C(1)-未取代的烯醇铵与 β- 和 α,β-取代的三氟亚甲基酮的区域和对映选择性形式 [2 + 2] 环加成反应。在所有情况下，观察到[2 + 2]-环加成优先于替代的[4 + 2]-环加成，使β-内酯具有优异的非对映选择性和对映选择性（34个例子，高达>95:5 dr，>99： 1 呃）。该过程的区域选择性取决于两种反应组分上取代基的性质。当使用α,β-取代的三氟亚甲基酮或α-三烷基甲硅烷基乙酸衍生物时，仅观察到[2+2]环加成产物；当使用β-取代的三氟亚甲基酮和α-烷基-α-三烷基甲硅烷基乙酸作为反应物时，观察到[2+2]和[4+2]环加成产物，以[2+2]环加成作为主要反应产物。该方案中酸组分内的 α-甲硅烷基取代基的有益作用已通过对照实验得到证明。
• Weiguny, Jens; Schaefer, Hans J., Liebigs Annalen der Chemie, 1994, # 3, p. 235 - 242
  作者：Weiguny, Jens、Schaefer, Hans J.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 22, page 68 - 71
  作者：

  DOI：——

  日期：——
• A convenient method for the synthesis of α-silylacetic acids
  作者：Alex V. Shtelman、James Y. Becker

  DOI：10.1016/j.tetlet.2008.03.050

  日期：2008.5

  A method is described for the preparation of alpha-silylacetic acids of the type R(3)SiCH(2)CO(2)H by treating trimethylsilyl acetate with LDA followed by quenching with chlorosilanes. (C) 2008 Elsevier Ltd. All rights reserved.