5-allyl-3-phenylfuran-2(5H)-one | 1427729-81-4

• 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-allyl-3-phenylfuran-2(5H)-one
• 英文别名: 4-phenyl-2-prop-2-enyl-2H-furan-5-one
• CAS: 1427729-81-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KPKFSMPYNVGQFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基环丙基-2-烯-1-羧酸 在 rhodium(II) pivalate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.17h， 生成 5-allyl-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Selective Syntheses of Δ^α,β and Δ^β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements

  摘要：

  Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Delta(beta,gamma) butenolides via a Cialsen rearrangement or to the corresponding Delta(alpha,beta) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.

  DOI：

  10.1021/ol400264a

文献信息

• Palladium-Catalyzed Asymmetric Allylic Alkylation of Cyclic Dienol Carbonates: Efficient Route to Enantioenriched γ-Butenolides Bearing an All-Carbon α-Quaternary Stereogenic Center
  作者：Jeremy Fournier、Oscar Lozano、Candice Menozzi、Stellios Arseniyadis、Janine Cossy

  DOI：10.1002/anie.201206368

  日期：2013.1.21

  Allyl dienol carbonates (1) served as substrates for the title reaction to afford the furanones 2 in both high yields and high enantioselectivities. These furanones were eventually converted into valuable building blocks including γ‐tertiary and γ‐quaternary furanones (3) as well as β‐quaternary butyrolactones (4). This method was used as a key step in the total synthesis of (−)‐nephrosteranic acid

  α，β，γ：碳酸烯丙二烯酯（1）作为标题反应的底物，以高收率和高对映选择性同时提供呋喃酮2。这些呋喃酮最终被转化为有价值的结构单元，包括γ-叔和γ-季呋喃酮（3）以及β-季丁内酯（4）。该方法被用作（-）-肾甾酸和（-）-木纤维酸的全合成过程中的关键步骤。
• 3 AND 5 ALKYL AND PHENYL 4-(HYDROXY OR ACYLOXY)-ALKYL SUBSTITUTED 2(5H)-FURANONES AS ANTI-INFLAMMATORY AGENTS
  申请人：Allergan

  公开号：EP0755389A1

  公开（公告）日：1997-01-29
• US5451686A
  申请人：——

  公开号：US5451686A

  公开（公告）日：1995-09-19
• [EN] 3 AND 5 ALKYL AND PHENYL 4-(HYDROXY OR ACYLOXY)-ALKYL SUBSTITUTED 2(5H)-FURANONES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] 2(5H)-FURANONES SUBSTITUES PAR ALKYLE ET PHENYLE EN POSITION 3 ET 5 ET PAR (HYDROXY OU ACYLOXY)-ALKYLE EN POSITION 4 UTILISES EN TANT QU'AGENTS INFLAMMATOIRES
  申请人：ALLERGAN

  公开号：WO1995028394A1

  公开（公告）日：1995-10-26

  (EN) Novel anti-inflammatory furanone compounds have formula (1), where R1 independently is H, phenyl, C1-C6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl of 1 to 9 carbons and n is an integer having the values of 1 or 2, and where when n is 1, the R1 group is attached either to the 3 or to the 5 position of the 2-furanone, when n is 2, then R1 is attached to both the 3 and 5 positions, with the proviso that when n is 1, then R1 is not H; Y1 is H, alkyl of 1 to 20 carbons, phenyl C1-C20 alkyl, C1-C20 alkenyl containing one or more olefinic bonds, PO(OH)2, PO(OH)OR2, PO(OH)R2, PO(OR2)2, where R2 is independently alkyl of 1 to 20 carbons, phenyl, halogen substituted phenyl or C1-C6 alkyl substituted phenyl, further Y1 is CO-R3, CO-OR3, CONHR3, SO2R3, SO2NHR3, (CH2)p-O-R3, or (CH2)p-O-(CH2)m-O-R3, where p and m are integers and are independently 1 to 20 and R3 is H, C1-C20 alkyl, C1-C20 alkenyl containing one or more olefinic bonds, phenyl, halogen substituted phenyl or C1-C6 alkyl substituted phenyl, with the proviso that when Y1 is CO-OR3 or CONHR3, then R3 is not hydrogen; Y2 is H, an alkyl group of 1 to 25 carbons, phenyl, naphthyl, phenyl (C1-C20)alkyl-, naphthyl (C1-C20)alkyl-, halogen substituted phenyl, C1-C6 alkyl substituted phenyl, halogen substituted naphthyl, C1-C6 substituted naphthyl.(FR) La présente invention concerne de nouveaux composés anti-inflammatoires à base de furanones représentés par la formule générale (1). Dans cette formule générale (1), R1 représente indépendamment H, phényle, phényle à substitution alkyle C1-C6, phényle à substitution halogène, ou alkyle portant 1 à 9 carbones, n étant un entier valant 1 ou 2, et lorsque n vaut 1, le groupe R1 est rattaché soit en position 3 ou 5 du 2-furanone, ou, lorsque n vaut 2, le groupe R1 est rattaché en même temps aux deux positions 3 et 5, sous réserve que lorsque n vaut 1 R1 soit différent de H; Y1 représente H, alkyle portant 1 à 20 carbones, phényle-alkyle C1-C20, alcényle C1-C20 portant au moins une liaison oléfinique, PO(OH)2, PO(OH)OR2, PO(OH)R2, PO(OR2)2, R2 représentant indépendamment alkyle à 1 à 20 carbones, phényle, phényle à substitution halogène ou phényle à substitution alkyle C1-C6, et en outre, Y1 représente CO-R3, CO-OR3, CONHR3, SO2R3, SO2NHR3, (CH2)p-O-R3 ou (CH2)p-O-(CH2)m-O-R3, p et m étant des entiers valant indépendamment 1 à 20, R3 représentant H, alkyle C1-C20, alcényle C1-C20 portant au moins une liaison oléfinique, phényle, phényle à substitution halogène ou phényle à substitution alkyle C1-C6, sous la réserve que, lorsque Y1 représente CO-OR3 ou CONHR3 R3 ne soit pas hydrogène; Y2 représente H, un groupe alkyle portant 1 à 25 carbones, phényle, naphtyle, phényle-alkyle (C1-C20), naphthyle-alkyle (C1-C20), phényle à substitution halogène, phényle à substitution alkyle C1-C6, naphtyle à substitution halogène, naphthyle à substitution C1-C6.
• Selective Syntheses of Δ^α,β and Δ^β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements
  作者：Xiaocong Xie、Yi Li、Joseph M. Fox

  DOI：10.1021/ol400264a

  日期：2013.4.5

  Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Delta(beta,gamma) butenolides via a Cialsen rearrangement or to the corresponding Delta(alpha,beta) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.