2-phenyl-5-propylfuran | 18150-85-1

• 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: 2-phenyl-5-propylfuran
• CAS: 18150-85-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: KAHOHUNIGHPDFE-UHFFFAOYSA-N

物化性质

• 沸点：
  104-105 °C(Press: 0.7 Torr)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-二氮杂-1-苯乙酮 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 48.33h， 生成 2-phenyl-5-propylfuran
  参考文献：
  名称：

  Cyclization Reactions of Rhodium Carbene Complexes. Effect of Composition and Oxidation State of the Metal

  摘要：

  Treatment of o-(1,7-octadiynyl)benzoyldiazoethane with rhodium(II) octanoate in pentane resulted in a double internal/internal alkyne insertion reaction producing a labile bicyclo[4.1.0]hept-1(7)ene derivative which readily undergoes a Diels-Alder reaction with diphenylisobenzofuran. Changing the solvent from pentane to CH2Cl2 afforded a 2:1 mixture of cis- and trans-alkenyl-substituted indenones. Stepwise cyclization involving a set of dipolar intermediates occurs in CH2Cl2 whereas metallocyclobutenes are involved when pentane is used as the solvent. The rhodium(II) carboxylate catalyzed reaction of unsymmetrically substituted cyclopropenes gives substituted furans derived from cleavage of the less substituted beta-bond. Thus, treatment of 3-benzoyl-3-methyl-1-(n-butyl)cyclopropene with Rh2OAc4 afforded a 26:1 mixture of 2-phenyl-3-methyl-4-(n-butyl)- and 2-phenyl-3-methyl-5-(n-butyl)furan. In contrast, the [ClRh(CO)(2)](2)-catalyzed reaction resulted in cleavage of the more substituted sigma-bond producing only 2-phenyl-3-methyl-5-(n-butyl)furan. Both reactions involve electrophilic attack of the rhodium metal on the less substituted carbon atom of the cyclopropene pi-bond to give the most stabilized cyclopropyl carbocation. Ring opening followed by rapid electrocyclization to the furan occurs with the Rh(IH) catalyst. With the Rh(I) catalyst, the ring-opened species preferentially cyclizes to a metallocyclobutene intermediate which then equilibrates with the thermodynamically more stable isomer prior to furan formation. The Rh(I)-catalyzed reaction of 3-benzoyl-1-propylcyclopropene with various terminal alkynes gives 4-alkyl-4-propyl-7-phenyloxepins in good yield. These reactions involve electrophilic attack of the rhodium metal on the more substituted carbon of the cyclopropene; pi-bond to give a rhodium carbene complex, This metallo carbenoid undergoes a subsequent [2 + 2] cycloaddition with terminal acetylenes, The resulting rhodacycle rearranges by a formal 1,5-sigmatropic shift, and this is followed by reductive elimination of rhodium to produce the observed oxepin.

  DOI：

  10.1021/jo962271r

文献信息

• A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F₅
  作者：Robert J. Lee、Martin R. Lindley、Gareth J. Pritchard、Marc C. Kimber

  DOI：10.1039/c7cc03229c

  日期：——

  Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant

  利用了Appel反应条件来影响内合成过氧化物的温和生物合成激发的脱水作用，以递送多取代的富电子呋喃。与传统的脱水程序不同，此方法不含金属和酸，可以在氧化还原中性条件下实现。通常适用于一定范围的芳基和烷基取代的内过氧化物，并且对官能团具有耐受性。此外，该程序已用于提供呋喃脂肪酸（FFA）F 5的有效全合成。
• A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans
  作者：Stanley Chang、Saheena Desai、Daniel B. Leznoff、Nabyl Merbouh、Robert Britton

  DOI：10.1002/ejoc.201300305

  日期：2013.6

  Feist–Benary furan synthesis has been developed that involves a lithium aldol reaction between a methyl ketone and an α-chloroaldehyde followed by a thermally induced tetrahydrofuran formation/dehydration sequence and affords 2,5-disubstituted furans in good overall yield. This process is demonstrated on multigram scale and is amenable to the production of symmetric or asymmetric furans that incorporate

  已经开发了一种改进的 Feist-Benary 呋喃合成，它涉及甲基酮和 α-氯醛之间的锂醇醛反应，然后是热诱导的四氢呋喃形成/脱水序列，并以良好的总产率提供 2,5-二取代呋喃。该过程在多克规模上得到证明，并且适用于生产包含一系列取代基（例如，芳基、叔丁基、二茂铁基）的对称或不对称呋喃。
• A simple synthesis of dienones via isomerization of alkynones effected by palladium catalysts
  作者：Barry M. Trost、Thomas. Schmidt

  DOI：10.1021/ja00215a051

  日期：1988.3

  Les alcynones sont preparees a partir d'acides N-methyl O-methyl hydroxamiques et d'alcynes lithies. L'isomerisation de ces alcynones en dienones s'effectue avec une excellente chimioselectivite

  Les alcynones sont 制备了一部分 N-甲基 O-甲基异羟肟酸和 d'alcynes lithies。L'异构化 de ces alcynones en dinones s'effectue avec uneexcelle chimioselectivite
• Efficient Synthesis of 2-Mono- and 2,5-Disubstituted Furans via the CuI-Catalyzed Cycloisomerization of Alkynyl Ketones
  作者：Alexander V. Kel'i、Vladimir Gevorgyan

  DOI：10.1021/jo010832v

  日期：2002.1.1

  A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

  开发了一种温和，通用，有效的方法，该方法通过CuI催化的炔基酮的环异构化反应合成2-单取代和2,5-二取代的呋喃。结果表明，使用该方法可轻松合成同时含有酸和碱不稳定基团的呋喃。提出了这种转换的合理机制。
• Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans
  作者：Xiaojun Hu、Bingwei Zhou、Hongwei Jin、Yunkui Liu、Liming Zhang

  DOI：10.1039/d0cc01238f

  日期：——

  An efficient synthesis of 2,5-disubstituted furans directly from alkynyl ketones has been developed via tandem gold(I)-catalyzed isomerization of alkynyl ketones to allenyl ketones and cycloisomerization. The key to the success of this chemistry is the use of a biphenyl-2-ylphosphine ligand featuring a critical remote tertiary amino group.

  通过串联金（I）催化的炔基酮异构化为烯丙基酮和环异构化，已经开发了直接从炔基酮直接合成2,5-二取代的呋喃的方法。该化学方法成功的关键是使用具有关键远程叔氨基的联苯-2-基膦配体。