trans-5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester
• 英文别名: ethyl trans-5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carboxylate；ethyl (2S,3S)-2-benzoyl-3,5-diphenyl-2,3-dihydrofuran-4-carboxylate
• 化学式: C₂₆H₂₂O₄
• 分子量: 398.458
• InChiKey: BYNYVHIXFHHLJQ-OFVILXPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alpha-氯乙酰苯 、 (Z)-2-benzoyl-3-phenylacrylic acid ethyl ester 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以79%的产率得到trans-5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  2,3-二氢呋喃合成中的吡啶鎓叶立德

  摘要：

  已经开发了一种从容易获得的起始烯酮和吡啶鎓盐合成 2,3-二氢呋喃的新方法。该协议可以为以立体选择性方式制备 2,3-二氢呋喃提供一种新颖有效的方法。为了提高该反应的效率，还开发了一锅法，其中吡啶鎓盐由相应的卤化物原位生成。

  DOI：

  10.1055/s-2006-926300

文献信息

• α-Nitro carbonyl compounds in the synthesis of 2,3-dihydrofurans
  作者：Che-Ping Chuang、Kuang-Po Chen、Yu-Lin Hsu、An-I. Tsai、Shui-Te Liu

  DOI：10.1016/j.tet.2008.05.122

  日期：2008.8

  A new method for the synthesis of 2,3-dihydrofurans from readily available starting enones and alpha-nitro carbonyl compounds has been developed. This protocol can provide a novel and effective methodology for the preparation of 2,3-dihydrofurans in a stereoselective fashion. With 1,4-dien-3-ones, 2,3-dihydrofurans and cyclohexenecarboxylates were produced and high chemoselectivity was observed in different solvents. (C) 2008 Elsevier Ltd. All rights reserved.
• N-Phenacylpyridinium bromides in the one-pot synthesis of 2,3-dihydrofurans
  作者：Che-Ping Chuang、Kuang-Po Chen

  DOI：10.1016/j.tet.2011.12.035

  日期：2012.2

  A one-pot three-component process for the synthesis of highly functionalized 2,3-dihydrofurans from 1,3-dicarbonyl compounds, aromatic aldehydes, and N-phenacylpyridinium bromides has been developed. Benzylidene 1,3-dicarbonyl compounds could be generated in situ from aromatic aldehydes and 1,3-dicarbonyl compounds and then reacted smoothly with N-phenacylpyridinium bromides to produce 2,3-dihydrofurans in moderate to good yields. Piperidine/acetonitrile is the optimal condition for this process. To increase the efficiency of this reaction, this one-pot process was also conducted solvent-free under classical heating conditions and grinding conditions. (C) 2012 Elsevier Ltd. All rights reserved.