3-Methylidenespiro[chromene-2,1'-cyclohexane]-4-one | 291290-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Methylidenespiro[chromene-2,1'-cyclohexane]-4-one
• 英文别名: 3-methylidenespiro[chromene-2,1'-cyclohexane]-4-one
• CAS: 291290-83-0
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: UAEVLOZMPINDNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  phenylhydroxamoyl chloride 、 3-Methylidenespiro[chromene-2,1'-cyclohexane]-4-one 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到C₂₂H₂₁NO₃
  参考文献：
  名称：

  Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels–Alder reactions

  摘要：

  The locked s-cis enone system present in 3-methylenequinol-4-ones and chroman-4-ones offers substantial further synthetic opportunities as illustrated by the ability to function as a 2 pi-component in 1,3-dipolar cycloaddition reactions, or as a 2 pi- or 4 pi-component in Diels-Alder reactions. Cascade molecular queuing-cycloadditions/cyclocondensation are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01177-1
• 作为产物：
  描述：

  环己乙炔 、 2-碘苯酚 、 一氧化碳 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 甲苯 为溶剂， 45.0~70.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以67%的产率得到3-Methylidenespiro[chromene-2,1'-cyclohexane]-4-one
  参考文献：
  名称：

  Synthesis of quinol-4-ones and chroman-4-ones via a palladium-catalysed cascade carbonylation–allene insertion

  摘要：

  Palladium(0)-catalysed termolecular queuing processes involving oxidative addition to aryl iodides followed by low pressure carbonylation, allene insertion and capture of the resulting pi-allyl palladium(II) species by an internal O- or N-nucleophile occur in good yields. One-pot 3-methylene chromanone/quinolone synthesis-Michael addition-stereoselective reduction are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01176-x

文献信息

• Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels–Alder reactions
  作者：Ronald Grigg、Angela Liu、Duncan Shaw、Selvaratnam Suganthan、Melanie L Washington、Diane E Woodall、Gnanamoly Yoganathan

  DOI：10.1016/s0040-4039(00)01177-1

  日期：2000.9

  The locked s-cis enone system present in 3-methylenequinol-4-ones and chroman-4-ones offers substantial further synthetic opportunities as illustrated by the ability to function as a 2 pi-component in 1,3-dipolar cycloaddition reactions, or as a 2 pi- or 4 pi-component in Diels-Alder reactions. Cascade molecular queuing-cycloadditions/cyclocondensation are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of quinol-4-ones and chroman-4-ones via a palladium-catalysed cascade carbonylation–allene insertion
  作者：Ronald Grigg、Angela Liu、Duncan Shaw、Selvaratnam Suganthan、Diane E Woodall、Gnanamoly Yoganathan

  DOI：10.1016/s0040-4039(00)01176-x

  日期：2000.9

  Palladium(0)-catalysed termolecular queuing processes involving oxidative addition to aryl iodides followed by low pressure carbonylation, allene insertion and capture of the resulting pi-allyl palladium(II) species by an internal O- or N-nucleophile occur in good yields. One-pot 3-methylene chromanone/quinolone synthesis-Michael addition-stereoselective reduction are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.