2,2-dimethyl-6-[2-(trimethylsilyloxy)-2-phenylethyl]-4H-1,3-dioxin-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-6-[2-(trimethylsilyloxy)-2-phenylethyl]-4H-1,3-dioxin-4-one
• 英文别名: 6-(2-phenyl-2-trimethylsiloxyethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one；2,2-Dimethyl-6-(2-phenyl-2-trimethylsilyloxyethyl)-1,3-dioxin-4-one；2,2-dimethyl-6-(2-phenyl-2-trimethylsilyloxyethyl)-1,3-dioxin-4-one
• 化学式: C₁₇H₂₄O₄Si
• 分子量: 320.461
• InChiKey: WYRCALJVZVVHQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-[2-(trimethylsilyloxy)-2-phenylethyl]-4H-1,3-dioxin-4-one 在 三氟乙酸 作用下， 生成 6-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid

  摘要：

  The vinylogous aldol reaction of O-silyl dienolates deriving from 2,2-dimethyl-[1,3]-dioxin-4-ones proceeds in moderate to excellent yields in the presence of catalytic amounts of PhCOOH under solvent-free conditions. Modest to good yields can be obtained by using silica gel or 3 A molecular sieves as heterogeneous catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.152
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 咪唑 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2,2-dimethyl-6-[2-(trimethylsilyloxy)-2-phenylethyl]-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  酰基乙烯酮与 α-羟基酮反应合成酰基呋喃酮：在一步多组分合成 Cadiolide B 及其类似物中的应用

  摘要：

  在碱性条件下，在羟基酮的存在下，通过相应的二恶英酮的热裂解，以一步法制备了官能化的酰基呋喃酮。添加醛作为第三个反应伙伴时也会发生多组分反应，从而快速获得卡地内酯 B 及其类似物。

  DOI：

  10.1002/ejoc.201300166

文献信息

• The Mukaiyama Aldol and Mukaiyama–Michael Reactions Promoted by Commercially Available Molecular Sieves
  作者：Shunichi Hashimoto、Masahiro Anada、Takuya Washio、Yudai Watanabe

  DOI：10.3987/com-09-s(s)133

  日期：——

  The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 angstrom molecular sieves (4 angstrom MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles for this reaction. For the first time, it has been found that 4 angstrom MS can promote the Mukaiyama Michael addition reactions of silyl ketene acetals to alpha,beta-enones.
• Versatile Synthesis of Acylfuranones by Reaction of Acylketenes with α-Hydroxy Ketones: Application to the One-Step Multicomponent Synthesis of Cadiolide B and Its Analogues
  作者：Philippe Alexandre Peixoto、Agathe Boulangé、Stéphane Leleu、Xavier Franck

  DOI：10.1002/ejoc.201300166

  日期：2013.6

  Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues.

  在碱性条件下，在羟基酮的存在下，通过相应的二恶英酮的热裂解，以一步法制备了官能化的酰基呋喃酮。添加醛作为第三个反应伙伴时也会发生多组分反应，从而快速获得卡地内酯 B 及其类似物。
• Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid
  作者：Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetlet.2005.06.152

  日期：2005.9

  The vinylogous aldol reaction of O-silyl dienolates deriving from 2,2-dimethyl-[1,3]-dioxin-4-ones proceeds in moderate to excellent yields in the presence of catalytic amounts of PhCOOH under solvent-free conditions. Modest to good yields can be obtained by using silica gel or 3 A molecular sieves as heterogeneous catalysts. (c) 2005 Elsevier Ltd. All rights reserved.