3-(cyclohex-2-enyl)-4-hydroxy-6-methyl-pyran-2-one | 115580-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(cyclohex-2-enyl)-4-hydroxy-6-methyl-pyran-2-one
• 英文别名: 3-(Cyclohex-2-en-1-yl)-4-hydroxy-6-methyl-2H-pyran-2-one；3-cyclohex-2-en-1-yl-4-hydroxy-6-methylpyran-2-one
• CAS: 115580-37-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: AUBATJJQRXQLRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(cyclohex-2-enyl)-4-hydroxy-6-methyl-pyran-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到3-cyclohexyl-4-hydroxy-6-methyl-2-pyrone
  参考文献：
  名称：

  Palladium-catalyzed C-alkylations of the highly acidic and enolic triacetic acid lactone. Mechanism and stereochemistry

  摘要：

  DOI：

  10.1021/jo00257a023
• 作为产物：
  描述：

  3-乙酰氧基环己烯 在 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 17.0h， 生成 3-(cyclohex-2-enyl)-4-hydroxy-6-methyl-pyran-2-one
  参考文献：
  名称：

  钯催化的模型聚酮化合物的区域选择性烯丙基化中的铜保护：3,5-二氧己酸甲酯

  摘要：

  通过钯催化的铜（II）配合物1a的钯催化烯丙基化反应，即使在仲和叔基团的情况下，也可以在C-2位置完成模型聚酮化合物系统3,5-二氧己酸甲酯的区域选择性烯丙基化。初步结果表明，钴（II）配合物1b也可能有用。所得二酮酸酯3的环化，得到在C-3区域选择性烯丙基化的三乙酸内酯衍生物5。

  DOI：

  10.1016/s0040-4039(00)99414-0

文献信息

• Palladium catalyzed allylic C-alkylation of highly acidic and enolic heterocyclic substrates: tetronic acid and triacetic acid lactone
  作者：Marcial Moreno-Mañas、Maria Prat、Jordi Ribas、Albert Virgili

  DOI：10.1016/s0040-4039(00)80156-2

  日期：——

  Tetronic acid (pKa 3.76) and triacetic acid lactone (pKa 4.94) have been alkylated at their active carbon atoms by means of thermodinamically controlled palladium catalyzed allylic alkylations.

  已通过热丁二胺控制的钯催化的烯丙基烷基化作用将四氢苯甲酸（pK a 3.76）和三乙酸内酯（pK a 4.94）烷基化。
• Regioselective Heterocyclization of 3-(Cyclohex-2′-enyl)-4-hydroxy-6-methylpyran-2-one
  作者：Krishna C. Majumdar、Subhojit Ghosh

  DOI：10.1007/s007060200109

  日期：2002.9.1

  Regioselective heterocyclization of 3-(cyclohex-2-enyl)-4-hydroxy-6-methyl pyran-2-one with various reagents afforded different heterocycles. With N-iodosuccinimide in acetonitrile at 0-5degreesC it gave 6-methyl-9'-iodo-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, with C5H5NHBr3 or C6H12N4HBr3 in CHCl3 at 0-5degreesC it furnished 6-methyl-9'-bromo-2'-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one. Cold concentrated H2SO4 lead to 6-methyl-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, whereas PdCl2(PhCN)(2) in C6H6 at 80degreesC afforded 9-methyl benzofuro[3,2-c]pyran-2-one.
• Solid‐State Regioselective Cyclization Initiated by the Electrophilic Attack on the Double Bond by N‐Bromosuccinimide on Montmorillonite K‐10 Clay Support under Microwave Irradiation
  作者：K. C. Majumdar、H. Rahaman、B. Roy

  DOI：10.1080/00397910701228992

  日期：2007.5

  3-AllyI-4-hydroxy-coumarins and pyrones were regioselectively cyclized with N-bromosuccinimide (NBS) on solid phase under microwave irradiation in excellent yield. NBS on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective cyclization has been used for the first time.
• Stannic Chloride–Iodine: An Efficient Reagent for Regioselective Synthesis of Furan–Fused Heterocycles
  作者：K. C. Majumdar、A. Biswas、P. P. Mukhopadhyay

  DOI：10.1080/00397910701470982

  日期：2007.8.1

  SnCl4-I-2-mediated cyclization of ortho-cyclohexenyl phenol and ortho-cyclohexenyl enol derivatives of coumarin, uracil, dimedone, and pyrone at room temperature for 1 h give the linear cyclized products in 78-90% yield, which, on treatment with 10% Pd-C at 250 degrees C for 1-2 h, afford corresponding aromatized products in 80-84% yield.
• MORENO-MANAS, MARCIAL;RIBAS, JORDI;VIRGILI, ALBERT, J. ORG. CHEM., 53,(1988) N2, C. 5328-5335
  作者：MORENO-MANAS, MARCIAL、RIBAS, JORDI、VIRGILI, ALBERT

  DOI：——

  日期：——