methyl α-<(trimethylsilyl)methyl>acetoacetate | 67262-88-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl α-<(trimethylsilyl)methyl>acetoacetate
• 英文别名: methyl 3-oxo-2-(trimethylsilylmethyl)butyroate；methyl 3-oxo-2-trimethylsilylmethylbutyrate；methyl 2-(trimethylsilyl)acetoacetate；Methyl 3-oxo-2-(trimethylsilylmethyl)butanoate
• CAS: 67262-88-8
• 化学式: C₉H₁₈O₃Si
• 分子量: 202.326
• InChiKey: ROQRVKQQYDXGMS-UHFFFAOYSA-N

物化性质

• 沸点：
  40-44 °C(Press: 0.1 Torr)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl α-<(trimethylsilyl)methyl>acetoacetate 在 boron trifluoride diacetate 作用下， 以 乙醚 、 氘代氯仿 为溶剂， 反应 2.67h， 生成 环己乙酸,4-[4-(4-氨基-7,7-二甲基-7H-嘧啶并[4,5-b][1,4]噁嗪-6-基)苯基]-,顺-
  参考文献：
  名称：

  Fleming, Ian; Patel, Shailesh K.; Urch, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 115 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-oxo-2-<(phenylthio)trimethylsilylmethyl>butyrate 在 镍 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以98%的产率得到methyl α-<(trimethylsilyl)methyl>acetoacetate
  参考文献：
  名称：

  Fleming, Ian; Patel, Shailesh K.; Urch, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 115 - 124

  摘要：

  DOI：

文献信息

• 3-Chloro-2-[(diethoxyphosphoryl)oxy]-1-propene: a new reagent for a one-pot cyclopentenone annelation. Synthesis of desoxyallethrolone, cis-jasmone, and methylenomycin B
  作者：S. C. Welch、J. M. Assercq、J. P. Loh、S. A. Glase

  DOI：10.1021/jo00384a012

  日期：1987.4
• Fleming, Ian; Goldhill, Jon, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1493 - 1498
  作者：Fleming, Ian、Goldhill, Jon

  DOI：——

  日期：——
• γ-Silyl-stabilized tertiary ions? Solvolysis of­4-(trimethylsilyl)-2-chloro-2-methylbutane
  作者：Leon J. Tilley、V. J. Shiner

  DOI：10.1002/(sici)1099-1395(199907)12:7<564::aid-poc164>3.0.co;2-2

  日期：1999.7

  Rate constant, isotope-effect, and product studies of the solvolysis of 4-(trimethylsilyl)-2-chloro-2-methylbutane, 11, and its carbon analog, 2-chloro-2,5,5-trimethylhexane, 10, in aqueous ethanol and aqueous 2,2,2-trifluoroethanol (TFE) indicate very little participation of the gamma-silyl substituent. These results are in sharp contrast to earlier reports on secondary gamma-silyl substituted systems, in which the beck lobe of the silicon-carbon bond has been shown to overlap with the carbocation p-orbital to form a so-called 'percaudally' stabilized intermediate. While the solvolytic behaviors of 11 and 10 are nearly identical in ethanol, differences in the TFE lead to the conclusion that there is a minor amount of participation by the silyl substituent in that solvent. Interestingly, this observation lends credence to an earlier suggestion that TFE is better than ethanol at stabilizing more highly delocalized ions. Copyright (C) 1999 John Wiley st Sons, Ltd.
• FLEMING I.; GOLDHILL J., J. CHEM. SOC. PERKIN TRANS., 1980, PART 1, NO 7, 1493-1498
  作者：FLEMING I.、 GOLDHILL J.

  DOI：——

  日期：——
• Fleming, Ian; Patel, Shailesh K.; Urch, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 115 - 124
  作者：Fleming, Ian、Patel, Shailesh K.、Urch, Christopher J.

  DOI：——

  日期：——