ethyl 4-(1,3-benzodioxol-5-carbonyl)-2-(4-methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylate

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: ethyl 4-(1,3-benzodioxol-5-carbonyl)-2-(4-methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylate
• 英文别名: ethyl (2R,3S,4R)-4-(1,3-benzodioxole-5-carbonyl)-2-(4-methoxyphenyl)-5-oxooxolane-3-carboxylate
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: PUSPDLIXVINEOI-HBFSDRIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4-(1,3-benzodioxol-5-carbonyl)-2-(4-methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylate 在 palladium on activated charcoal 氢气 、 甲基磺酰氯 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Vicinal dianions of diethyl α-aroylsuccinates: a general synthetic route to α-aroyl- and α-arylidene-γ-butyrolactones

  摘要：

  Vicinal dianions derived from diethyl alpha-aroylsuccinates were found to react with carbonyl compounds beta-regioselectively to afford alpha-aroyl-gamma-butyrolactones, which were converted into alpha-arylidene-gamma-butyrolactones by reduction with H-2/Pd-C followed by elimination employing methanesulfonyl chloride in pyridine. The method provides a general and convenient route to alpha-aroyland alpha-arylidene-gamma-butyrolactones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01622-8
• 作为产物：
  描述：

  富马酸二乙酯 在 3-benzyl-5-(2-dihydroxyethyl)-4-methylthiazolium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 生成 ethyl 4-(1,3-benzodioxol-5-carbonyl)-2-(4-methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Vicinal dianions of diethyl α-aroylsuccinates: a general synthetic route to α-aroyl- and α-arylidene-γ-butyrolactones

  摘要：

  Vicinal dianions derived from diethyl alpha-aroylsuccinates were found to react with carbonyl compounds beta-regioselectively to afford alpha-aroyl-gamma-butyrolactones, which were converted into alpha-arylidene-gamma-butyrolactones by reduction with H-2/Pd-C followed by elimination employing methanesulfonyl chloride in pyridine. The method provides a general and convenient route to alpha-aroyland alpha-arylidene-gamma-butyrolactones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01622-8

文献信息

• Syntheses of (±)-thuriferic acid ethyl ester, its analogues and (±)-picropodophyllone
  作者：Manat Pohmakotr、Taweechote Komutkul、Patoomratana Tuchinda、Samrarn Prabpai、Palangpon Kongsaeree、Vichai Reutrakul

  DOI：10.1016/j.tet.2005.03.069

  日期：2005.5

  (±)-Thuriferic acid ethyl ester, its analogues as well as (±)-picropodophyllone have been prepared. The synthetic strategy is based on the utility of vicinal dianions derived from α-aroylsuccinic esters.

  已经制备了（±）-硫代磷酸乙酯，其类似物以及（±）-吡鬼臼酮。合成策略基于衍生自α-芳酰基琥珀酸酯的邻位二价阴离子的效用。
• Vicinal dianions of diethyl α-aroylsuccinates: a general synthetic route to α-aroyl- and α-arylidene-γ-butyrolactones
  作者：Manat Pohmakotr、Laddawan Sampaongoen、Arisara Issaree、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/s0040-4039(03)01622-8

  日期：2003.8

  Vicinal dianions derived from diethyl alpha-aroylsuccinates were found to react with carbonyl compounds beta-regioselectively to afford alpha-aroyl-gamma-butyrolactones, which were converted into alpha-arylidene-gamma-butyrolactones by reduction with H-2/Pd-C followed by elimination employing methanesulfonyl chloride in pyridine. The method provides a general and convenient route to alpha-aroyland alpha-arylidene-gamma-butyrolactones. (C) 2003 Elsevier Ltd. All rights reserved.