2,4-dimethoxyacetophenone trimethylsilyl enol ether | 125304-90-7

• 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: 2,4-dimethoxyacetophenone trimethylsilyl enol ether
• 英文别名: {[1-(2,4-dimethoxyphenyl)ethenyl]oxy}trimethylsilane；2,4-dimethoxy-α-(trimethylsiloxy)styrene；1-(2,4-dimethoxyphenyl)ethenoxy-trimethylsilane
• CAS: 125304-90-7
• 化学式: C₁₃H₂₀O₃Si
• 分子量: 252.386
• InChiKey: TXPSVGZWTZJCGR-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±27.0 °C(predicted)
• 密度：
  0.976±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxyacetophenone trimethylsilyl enol ether 在 六甲基磷酰三胺 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Drewes, Siegfried E.; Hogan, Craig J.; Kaye, Perry T., Journal of the Chemical Society. Perkin transactions I, 1989, p. 1585 - 1591

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 2,4-二甲氧基苯乙酮 在 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以60 %的产率得到2,4-dimethoxyacetophenone trimethylsilyl enol ether
  参考文献：
  名称：

  Sulfur‐Free Radical RAFT Polymerization of Methacrylates in Homogeneous Solution: Design of exo ‐Olefin Chain‐Transfer Agents (R−CH ₂ C(=CH ₂ )Z)

  摘要：

  AbstractIn this work, the development of exo‐olefin compounds (R−CH2C(=CH2)Z) as chain‐transfer agents for the sulfur‐free reversible addition‐fragmentation chain transfer (RAFT) radical polymerization of methacrylates in homogeneous solution is described. A series of exo‐olefin compounds with a methyl methacrylate (MMA) dimer structure as the R group and a substituted α‐methylstyrene unit as the −CH2C(=CH2)Z (Z: Ph−Y) group were synthesized and used for the radical polymerization of MMA in toluene and PhC(CF3)2OH. These compounds underwent transfer of the CH2C(=CH2)Z group via addition‐fragmentation of the propagating methacryloyl radical. More electron‐donating (Y) substituents, such as methoxy and dimethylamino groups, produced polymers with narrower molecular weight distributions. A continuous monomer addition method further improved molecular weight control and enabled the synthesis of colorless, sulfur‐free, multiblock copolymers of methacrylates in homogeneous solutions.

  DOI：

  10.1002/anie.202212633

文献信息

• Difluorohomologation of Ketones
  作者：Mikhail D. Kosobokov、Vitalij V. Levin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1021/acs.orglett.5b00097

  日期：2015.2.6

  CF2 fragment is described. The reaction involves silylation, room-temperature difluorocyclopropanation of silyl enol ethers, and selective ring opening of cyclopropanes under acidic conditions. The whole three-step sequence is conveniently performed in a one-pot mode.

  描述了一种使CF 2片段与酮同源的方法。该反应包括甲硅烷基化，甲硅烷基烯醇醚的室温二氟环丙烷化和在酸性条件下环丙烷的选择性开环。整个三步顺序可在一锅模式下方便地执行。
• Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins
  作者：Lun Li、Kimberly A. Wasik、Brian J. Frost、Laina M. Geary

  DOI：10.1016/j.tetlet.2019.151370

  日期：2020.1

  described. When DCA was used as a solution in diethyl ether, we found that the silyl group was transferred to the vinyl group, resulting in stereochemically pure tetrasubstituted olefins. However, when DCA was used as a solution in the more polar acetonitrile, protonation was the major pathway, and trisubstituted olefins were the dominant products.

  描述了甲硅烷基烯醇醚与二氯乙炔（DCA）的银催化反应。当将DCA用作乙醚溶液时，我们发现甲硅烷基转移到了乙烯基上，生成了立体化学纯的四取代烯烃。但是，当将DCA用作极性更大的乙腈中的溶液时，质子化是主要途径，而三取代的烯烃是主要产物。
• Importance of the Hydroxymethyk-quinuclidine Fragment in the Catalytic Asymmetric Aldol Reactions Utilizing Quaternary Ammonium Fluorides Derived from Cinchona Alkaloids
  作者：Takayuki Shioiri、Akemi Bohsako、Akira Ando

  DOI：10.3987/com-95-s28

  日期：——

  The hydroxymethyl-quinuclidine fragment in quaternary ammonium fluorides derived from cinchona alkaloids proved to play an important role on the stereochemical course in the fluoride ion catalyzed aldol reactions.
• DREWES, SIEGFRIED E.;HOGAN, CRAIG J.;KAYE, PERRY T.;ROOS, GREGORY H. P., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1585-1591
  作者：DREWES, SIEGFRIED E.、HOGAN, CRAIG J.、KAYE, PERRY T.、ROOS, GREGORY H. P.

  DOI：——

  日期：——