(E)-1-(furan-2-yl)-4-hydroxybut-2-en-1-one | 1005326-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(furan-2-yl)-4-hydroxybut-2-en-1-one
• CAS: 1005326-82-8
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: SCSJSWPZRHEOLU-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(furan-2-yl)-4-hydroxybut-2-en-1-one 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 2,2'-联呋喃
  参考文献：
  名称：

  Sc（OTf）3催化芳基环氧乙烷二酯与γ-羟基烯酮的反应合成2,5-二取代的呋喃

  摘要：

  通过在与γ-羟基烯酮的新反应中使用供体-受体环氧乙烷开发了2,5-二取代呋喃的便捷合成方法。发现Sc（OTf）3是最好的催化剂，在温和的反应条件下，以中等到良好的产率获得了2,5-二取代的呋喃。该反应的范围相当合适，可以合成具有芳基和杂芳族基团的二取代呋喃。

  DOI：

  10.1021/acs.joc.7b00133
• 作为产物：
  描述：

  乙醇醛二聚体 、 dimethyl (2-(furan-2-yl)-2-oxoethyl)phosphonate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 生成 (E)-1-(furan-2-yl)-4-hydroxybut-2-en-1-one
  参考文献：
  名称：

  Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons

  摘要：

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.

  DOI：

  10.1021/ja076802c

文献信息

• Chloramphenicol base chemistry. Part 10 1 : Asymmetric synthesis of α -hydroxy chiral alcohols via intramolecular Michael additions of γ -hydroxy- α , β -unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts
  作者：Haifeng Wang、Linjie Yan、Yan Wu、Fener Chen

  DOI：10.1016/j.tet.2017.03.076

  日期：2017.5

  γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE

  我们已经开发了氯霉素碱脲催化的γ-羟基-α，β-不饱和烯酮的分子内迈克尔加成。所得产物的氧化提供了以良好的效率和对映选择性容易地获得相应的α-羟基手性醇的反应，该反应显示出广泛的底物范围。通过合成（R）-2-羟基-4-苯基丁酸（R）-2-羟基-4-苯基丁酸酯进一步证明了该方法的实用性，这是构建ACE抑制剂盐酸贝那普利的关键组成部分。
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
• Synthesis of 2,5-Disubstituted Furans from Sc(OTf)₃ Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones
  作者：Keshab Mondal、Subhas Chandra Pan

  DOI：10.1021/acs.joc.7b00133

  日期：2017.4.21

  A convenient synthesis of 2,5-disubstituted furan was developed by employing donor–acceptor oxiranes in a new reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,5-disubstituted furans are obtained in moderate to good yields under mild reaction conditions. The scope of the reaction is quite decent, allowing for the synthesis of disubstituted furans having aryl and heteroaromatic

  通过在与γ-羟基烯酮的新反应中使用供体-受体环氧乙烷开发了2,5-二取代呋喃的便捷合成方法。发现Sc（OTf）3是最好的催化剂，在温和的反应条件下，以中等到良好的产率获得了2,5-二取代的呋喃。该反应的范围相当合适，可以合成具有芳基和杂芳族基团的二取代呋喃。