5-propylfuran-2(3H)-one | 26524-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-propylfuran-2(3H)-one
• 英文别名: 2(3H)-Furanone, 5-propyl-；5-propyl-3H-furan-2-one
• CAS: 26524-73-2
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: LQXOMGOPQGMWAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-propylfuran-2(3H)-one 在 sodium acetate 作用下， 以 乙酸酐 、 苯 为溶剂， 反应 1.0h， 生成 (4S,4aS,7aR)-4-Furan-2-yl-2-propyl-4a,7a-dihydro-4H-1,6,8-trioxa-s-indacene-5,7-dione
  参考文献：
  名称：

  3H-呋喃-2-酮的3-亚芳基衍生物。马来酸酐的合成与反应

  摘要：

  DOI：

  10.1007/bf02253159
• 作为产物：
  描述：

  3-庚炔酸 在 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以58%的产率得到5-propylfuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885

文献信息

• Enantioselective vinylogous Michael addition of β,γ-unsaturated butenolide to 2-iminochromenes
  作者：Vijay Gupta、Ravi P. Singh

  DOI：10.1039/c9nj01584a

  日期：——

  An efficient organocatalyzed asymmetric synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles via vinylogous Michael addition of non-activated β,γ-unsaturated butenolide to 2-iminochromenes has been realized.

  已经实现了通过将未活化的β，γ-不饱和丁烯内酯乙烯基键合到2-亚氨基色酮上的有效的有机催化不对称合成2-氨基-4-（2-呋喃酮）-4 H-亚甲基-3-腈。
• Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4<i>H</i>-chromene-3-carbonitriles
  作者：Vijay Gupta、Debashish Sahu、Shailja Jain、Kumar Vanka、Ravi P. Singh

  DOI：10.1039/c9ob01345h

  日期：——

  Highly syn-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium tert-butoxide has been realised. The reaction proceeds via a tandem Knoevenagel/Pinner/vinylogous Michael condensation.

  三种组分（水杨醛、马来酸二腈和丁烯酮）在钠叔丁醇存在下高度选择性地统一，实现了反应。该反应通过串联Knoevenagel/Pinner/亲烯Michael缩合进行。
• Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins
  作者：Madhu Sudan Manna、Vikas Kumar、Santanu Mukherjee

  DOI：10.1039/c2cc31700a

  日期：——

  A direct vinylogous Michael reaction of gamma-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (up

  借助新鉴定的奎宁衍生的双官能催化剂，开发了γ-取代的共轭丁烯内酯与硝基烯烃的直接乙烯基迈克尔反应，可合成具有连续四级和三级立体中心的致密功能化产物，并具有出色的非对映选择性（> 20：1 dr）和高对映选择性（高达99：1 er）。
• Et3N catalyzed direct α-addition cascade isomerization of deconjugated butenolides with α-ketoesters for the synthesis of α,γ-disubstituted butenolide derivatives
  作者：Zhe-Yao Huang、Hong Yang、Lin Zhou、Qing-Han Li、Zhi-Gang Zhao

  DOI：10.1016/j.tet.2022.132740

  日期：2022.4

  γ-disubstituted butenolides are widespread occurrences in numerous pharmacologically active molecules. In this paper, a highly efficient method for the synthesis of α,γ-disubstituted butenolide derivatives via a direct α-addition cascade isomerization of deconjugated butenolides with α-ketoesters using Et3N as catalyst, has been successfully developed. A series of α,γ-disubstituted butenolides have been

  α,γ-二取代丁烯内酯广泛存在于许多药理活性分子中。本文成功开发了一种以 Et 3 N 为催化剂，通过去共轭丁烯内酯与 α-酮酯直接 α-加成级联异构化合成 α,γ-二取代丁烯内酯衍生物的高效方法。一系列 α,γ-二取代丁烯内酯的产率高达 97%，具有优异的区域选择性（高达 >19/1 rr）。据我们所知，迄今为止，在直接α-加成级联异构化制备α,γ-二取代丁烯内酯中应用去共轭丁烯内酯尚无先例。
• Catalytic asymmetric formal γ-allylation of deconjugated butenolides
  作者：Amit K. Simlandy、Santanu Mukherjee

  DOI：10.1039/c5ob02362a

  日期：——

  A formal γ-allylation of deconjugated butenolides is reported based on a two-step sequence consisting of a catalytic diastereo- and enantioselective vinylogous nucleophilic addition to vinyl sulfones and Julia–Kocienski olefination. This highly modular approach delivers densely functionalized butenolides containing a quaternary stereogenic centre in excellent yield with high enantioselectivity.

  据报道，基于两个步骤的序列，由共轭非对映体和对映体选择性的乙烯基亲核加成到乙烯基砜中，并进行茱莉亚-科辛斯基的烯化反应，可以得到解偶联的丁烯内酯的正式γ-烯丙基化反应。这种高度模块化的方法以极高的收率和高对映选择性提供了含有四级立体异构中心的密集功能化丁烯内酯。