trans-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester
• 英文别名: ethyl 4-acetyl-5-methyl-3-phenyl-trans-2,3-dihydrofuran-2-carboxylate；ethyl 4-acetyl-2,3-dihydro-5-methyl-3-phenylfuran-2-carboxylate；ethyl 4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylate；ethyl (2S,3S)-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylate
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: LHABTOVEPNCEEC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 3.0h， 以44%的产率得到cis-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  基于1,4-二氮杂双环[2.2.2]辛烷（DABCO）催化卤化物与烯酮的反应，轻松合成高度官能化的二氢呋喃

  摘要：

  在1，4-二氮杂双环[2.2.2]辛烷（DABCO）存在下，用亲电子烯烃2处理卤化物5得到相应的二氢呋喃3和4，在大多数情况下以良好的至优异的产率和立体选择性。此外，在1，8-二氮杂双环[5.4.0]十一烷基-7-烯（DBU）的存在下，立体异构体3和4可以容易地彼此转化。

  DOI：

  10.1016/j.tet.2005.07.009
• 作为产物：
  描述：

  ethyl 4-acetyl-2-nitro-5-oxo-3-phenylhexanoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以48%的产率得到trans-4-acetyl-5-methyl-3-phenyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  10.1134/s1070428012070196

  摘要：

  DOI：

  10.1134/s1070428012070196

文献信息

• Pyridinium Ylides in the Synthesis of 2,3-Dihydrofurans
  作者：Che-Ping Chuang、An-I Tsai

  DOI：10.1055/s-2006-926300

  日期：——

  A new method for the synthesis of 2,3-dihydrofurans from readily available starting enones and pyridinium salts has been developed. This protocol can provide a novel and effective methodology for the preparation of 2,3-dihydrofurans in a stereoselective fashion. To increase the efficiency of this reaction the one-pot process was also developed, in which the pyridinium salts were generated in situ from

  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。
• Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles viapyridine catalyzed formal [4+1] annulation
  作者：Chun-Rong Liu、Ben-Hu Zhu、Jun-Cheng Zheng、Xiu-Li Sun、Zuowei Xie、Yong Tang

  DOI：10.1039/c0cc02347g

  日期：——

  A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, α-ylidene-β-diketones and α,β-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively, in up to 96% yield with high diastereoselectivities.

  已开发出一种吡啶催化的亚胺循环反应，该反应能生成二氢呋喃和二氢吡咯。在催化量的吡啶和Fe(Tcpp)Cl的存在下，α-亚胺-β-二酮和α,β-不饱和亚胺与二氮乙酸酯反应，分别提供二氢呋喃和二氢吡咯，产率高达96%，并且具有很高的立体选择性。
• Highly Diastereoselective and Enantioselective Formal [4 + 1] Ylide Annulation for the Synthesis of Optically Active Dihydrofurans
  作者：Jun-Cheng Zheng、Chun-Yin Zhu、Xiu-Li Sun、Yong Tang、Li-Xin Dai

  DOI：10.1021/jo801135j

  日期：2008.9.1

  On the basis of the reactions of camphor-derived sulfur ylide with alpha-ylidene-beta-diketones, highly efficient and selective synthesis of optically active dihydrofurans has been achieved.

  基于樟脑衍生的硫内鎓盐与α-亚丙基-β-二酮的反应，已经实现了光学活性二氢呋喃的高效和选择性的合成。
• 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.
• A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones
  作者：Zhanjun Yang、Mingjin Fan、Ruizhu Mu、Weimin Liu、Yongmin Liang

  DOI：10.1016/j.tet.2005.07.009

  日期：2005.9

  Treatment of halides 5 with electrophilic alkenes 2 afforded the corresponding dihydrofurans 3 and 4 in the presence of 1, 4-diazabicyclo[2.2.2]octane (DABCO) with good to excellent yields and in a stereoselective manner in most cases. Moreover, the stereoisomers 3 and 4 could be easily transformed each other in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

  在1，4-二氮杂双环[2.2.2]辛烷（DABCO）存在下，用亲电子烯烃2处理卤化物5得到相应的二氢呋喃3和4，在大多数情况下以良好的至优异的产率和立体选择性。此外，在1，8-二氮杂双环[5.4.0]十一烷基-7-烯（DBU）的存在下，立体异构体3和4可以容易地彼此转化。