4-Benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

• 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: 4-Benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: QZHUNOVBEZXHJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 在 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以89%的产率得到ethyl (2R*,3S*,4R*)-4-benzoyl-4-fluoro-5-oxo-2-phenyltetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  立体选择性合成1-氟-exo，exo -2,6-diaryl-3,7-dioxabicyclocyclo [3.3.0]辛烷：（±）-1-Fluoromembrine的合成

  摘要：

  描述了1-氟-exo，exo -2,6-二芳基-3,7-二氧杂双环[3.3.0]辛烷的立体选择性合成。合成策略涉及使用Selectfluor立体选择性地氟化3,4-反-4,5-顺-3-芳基-5-芳基对圆锥酸酯，以高收率得到相应的氟化对圆锥酸酯，以单一异构体的形式进行还原反应。的LiAlH 4或DIBALH接着酸或路易斯酸的条件下形成Furofuran型，得到了一系列1-氟的外型，外切-furofurans在中等产率。合成协议还提供了对（±）-1-氟甲基苯丙氨酸的访问。

  DOI：

  10.1021/acs.joc.5b00970
• 作为产物：
  描述：

  富马酸二乙酯 在 sodium ethanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 4-Benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester
  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

• Vicinal dianions of diethyl α-aroylsuccinates: preparation of functionalized-2,3-dihydrofurans and -furans, and diaxial 2,4-diaryl-3,7-dioxabicyclo[3.3.0]octanes
  作者：Manat Pohmakotr、Arisara Issaree、Laddawan Sampaongoen、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/j.tetlet.2003.09.005

  日期：2003.10

  treatment of the adducts obtained with a catalytic amount of p-toluenesulfonic acid in refluxing toluene. cis-2,3-Dihydrofurans are used as precursors for the preparation of tetrasubstituted furans and diaxial 2,4-diaryl-3,7-dioxabicyclo[3.3.0]octanes.

  在回流甲苯中用催化量的对甲苯磺酸处理加成物后，α-芳基琥珀酸二乙酯的邻位二价阴离子与芳族醛反应，以提供功能化的2,3-二氢呋喃为主要产物，并与γ-丁内酯一起提供。顺式-2,3-二氢呋喃用作制备四取代呋喃和双轴2,4-二芳基-3,7-二氧杂双环[3.3.0]辛烷的前体。
• 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.
• Stereoselective Synthesis of 1-Fluoro-<i>exo</i>,<i>exo</i>-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
  作者：Teerachai Punirun、Darunee Soorukram、Chutima Kuhakarn、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1021/acs.joc.5b00970

  日期：2015.8.21

  Stereoselective synthesis of 1-fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes is described. The synthetic strategy involves stereoselective fluorination of 3,4-trans-4,5-cis-3-aroyl-5-arylparaconic esters using Selectfluor to afford the corresponding fluorinated paraconic esters in good yields as a single isomer, which are subjected to reduction employing LiAlH4 or DIBALH followed by furofuran

  描述了1-氟-exo，exo -2,6-二芳基-3,7-二氧杂双环[3.3.0]辛烷的立体选择性合成。合成策略涉及使用Selectfluor立体选择性地氟化3,4-反-4,5-顺-3-芳基-5-芳基对圆锥酸酯，以高收率得到相应的氟化对圆锥酸酯，以单一异构体的形式进行还原反应。的LiAlH 4或DIBALH接着酸或路易斯酸的条件下形成Furofuran型，得到了一系列1-氟的外型，外切-furofurans在中等产率。合成协议还提供了对（±）-1-氟甲基苯丙氨酸的访问。