5-allyl-4-hydroxy-6-methyl-2-pyrone | 131675-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-allyl-4-hydroxy-6-methyl-2-pyrone
• CAS: 131675-24-6
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: GCVOGCAQIPYAJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 1-phenylprop-2-ynyl carbonate 、 5-allyl-4-hydroxy-6-methyl-2-pyrone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以68%的产率得到(Z)-7-allyl-3-benzylidene-6-methyl-2H-furo[3,2-c]pyran-4(3H)-one
  参考文献：
  名称：

  Regiocontrolled Construction of Furo[3,2-c]pyran-4-one Derivatives by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 4-Hydroxy-2-pyrones

  摘要：

  The reaction of propargylic carbonates with 4-hydroxy-2-pyrones in the presence of a palladium catalyst is described. By the choice of the reaction temperature, two types of the substituted furo[3,2-c]pyran-4-one derivatives were regioselectively synthesized, respectively.

  DOI：

  10.1021/jo3027092
• 作为产物：
  描述：

  3-(2-propenyl)-2,4-pentanedione 在 N,N'-羰基二咪唑 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 5-allyl-4-hydroxy-6-methyl-2-pyrone
  参考文献：
  名称：

  Cervello, Jordi; Marquet, Jorge; Moreno-Manas, Marcial, Synthetic Communications, 1990, vol. 20, # 13, p. 1931 - 1941

  摘要：

  DOI：

文献信息

• Direct cyclization of 1,3-diaryl propargylic alcohols with β-dicarbonyl compounds by palladium-boric acid dual-catalyst system
  作者：Masahiro Yoshida、Shoko Ohno、Sayaka Eguchi、Tomotaka Mizuguchi、Kenji Matsumoto、Kosuke Namba

  DOI：10.1016/j.tet.2016.07.055

  日期：2016.9

  Palladium and boric acid-catalyzed cyclization of underivatized 1,3-diaryl propargylic alcohols with 1,3-cyclohexanediones has been developed. Boric acid plays a role for the efficient activation of the propargylic alcohols. Various substituted tetrahydrobenzofuranones were obtained in moderate to good yields. Reactions using 4-hydroxy-2-pyrones as the nucleophile also proceeded to afford the substituted

  已经开发了钯和硼酸与1，3-环己二酮对未衍生的1，3-二芳基炔丙醇的环化。硼酸对于有效活化炔丙醇起着作用。以中等至良好的产率获得了各种取代的四氢苯并呋喃酮。使用4-羟基-2-吡喃酮作为亲核试剂的反应也进行，得到取代的二氢呋喃基吡喃酮。
• Synthesis of pyrone-annulated 2-oxabicyclo[3.3.1]nonanes by palladium-catalyzed cyclization of 4-hydroxy-2-pyrones with allylic bisacetates
  作者：Masahiro Yoshida、Miki Shibata、Saaya Mukae、Kouki Kinoshita、Kenji Matsumoto、Tsukasa Hirokane

  DOI：10.1016/j.tetlet.2019.151262

  日期：2019.12

  Cyclization of 4-hydroxy-2-pyrones with allylic bisacetates by a palladium catalyst is described. Pyrone-annulated 2-oxabicyclo[3.3.1]nonane derivatives were regioselectively produced from the reaction of 4-hydroxy-2-pyrones with 1,4-diacetoxy-2-cyclohexene at high temperature. The reaction would proceed via a migration of the π-allylpalladium intermediate.

  描述了通过钯催化剂用烯丙基双乙酸酯对4-羟基-2-吡喃酮的环化。吡咯环化的2-氧杂双环[3.3.1]壬烷衍生物是由4-羟基-2-吡喃酮与1,4-二乙酰氧基-2-环己烯在高温下反应区域选择性生成的。该反应将通过π-烯丙基铝中间体的迁移而进行。
• GERVELLO, JORDI;MARQUET, JORGE;MORENO-MANAS, MARCIAL, SYNTH. COMMUN., 20,(1990) N3, C. 1931-1941
  作者：GERVELLO, JORDI、MARQUET, JORGE、MORENO-MANAS, MARCIAL

  DOI：——

  日期：——
• Cervello, Jordi; Marquet, Jorge; Moreno-Manas, Marcial, Synthetic Communications, 1990, vol. 20, # 13, p. 1931 - 1941
  作者：Cervello, Jordi、Marquet, Jorge、Moreno-Manas, Marcial

  DOI：——

  日期：——
• Regiocontrolled Construction of Furo[3,2-<i>c</i>]pyran-4-one Derivatives by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 4-Hydroxy-2-pyrones
  作者：Masahiro Yoshida、Tomomi Nakagawa、Kouki Kinoshita、Kozo Shishido

  DOI：10.1021/jo3027092

  日期：2013.2.15

  The reaction of propargylic carbonates with 4-hydroxy-2-pyrones in the presence of a palladium catalyst is described. By the choice of the reaction temperature, two types of the substituted furo[3,2-c]pyran-4-one derivatives were regioselectively synthesized, respectively.