2,2,6-trimethyl-5-(thiophen-3-yl)-4H-1,3-dioxin-4-one | 168636-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,6-trimethyl-5-(thiophen-3-yl)-4H-1,3-dioxin-4-one
• 英文别名: 2,2,6-Trimethyl-5-thiophen-3-yl-1,3-dioxin-4-one；2,2,6-trimethyl-5-thiophen-3-yl-1,3-dioxin-4-one
• CAS: 168636-91-7
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: FICVFQCEOQIMPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2,6-trimethyl-5-iodo-4H-1,3-dioxin-4-one 、 3-噻吩三氟硼酸钾 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氢氧化铵 作用下， 以 水 为溶剂， 反应 0.92h， 以73%的产率得到2,2,6-trimethyl-5-(thiophen-3-yl)-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters

  摘要：

  The high efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a-b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a-n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.027

文献信息

• Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters
  作者：Adriano S. Vieira、Rodrigo L.O.R. Cunha、Clécio F. Klitzke、Julio Zukerman-Schpector、Hélio A. Stefani

  DOI：10.1016/j.tet.2009.11.027

  日期：2010.1

  The high efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a-b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a-n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier Ltd. All rights reserved.