Methyl 2,3-dioxo-3-thiophen-2-ylpropanoate | 1610628-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,3-dioxo-3-thiophen-2-ylpropanoate
• 英文别名: methyl 2,3-dioxo-3-thiophen-2-ylpropanoate
• CAS: 1610628-76-6
• 化学式: C₈H₆O₄S
• 分子量: 198.199
• InChiKey: ZQLQGIHOOGORRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氧代-3-(2-噻吩基)丙酸甲酯 在 2,2,6,6-四甲基哌啶氧化物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 12.08h， 生成 Methyl 2,3-dioxo-3-thiophen-2-ylpropanoate 、 3-(thiophen-2-yl)-2-hydroxy-3-oxo-propionic acid methyl ester
  参考文献：
  名称：

  DDQ-mediated oxidation of sp3 C–H bond for the direct synthesis of vicinal tricarbonyl compounds

  摘要：

  A facile and direct synthetic method was developed for the construction of vicinal tricarbonyl compounds (VTCs) in moderate to excellent yields (46-92%), by treating the readily available 1,3-dicarbonyl compounds with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The reaction pathway involves the DDQ-mediated oxidative activation of sp(3) C-H bond and subsequent coupling to TEMPO to form the key intermediate TEMPO-substrate adduct, which can be further converted to VTC products promoted by DDQ (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.021

文献信息

• DDQ-mediated oxidation of sp3 C–H bond for the direct synthesis of vicinal tricarbonyl compounds
  作者：Zheng-Lin Wang、Xing-Lan An、Li-Shi Ge、Jing-Hai Jin、Xiaoyan Luo、Wei-Ping Deng

  DOI：10.1016/j.tet.2014.04.021

  日期：2014.6

  A facile and direct synthetic method was developed for the construction of vicinal tricarbonyl compounds (VTCs) in moderate to excellent yields (46-92%), by treating the readily available 1,3-dicarbonyl compounds with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The reaction pathway involves the DDQ-mediated oxidative activation of sp(3) C-H bond and subsequent coupling to TEMPO to form the key intermediate TEMPO-substrate adduct, which can be further converted to VTC products promoted by DDQ (C) 2014 Elsevier Ltd. All rights reserved.