5-Hydroxy-2-(4-methoxyphenyl)-1-benzofuran-4-carbaldehyde | 1173179-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-Hydroxy-2-(4-methoxyphenyl)-1-benzofuran-4-carbaldehyde
• 英文别名: 5-hydroxy-2-(4-methoxyphenyl)-1-benzofuran-4-carbaldehyde
• CAS: 1173179-02-6
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: BDIOAFXSQQXTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-碘代丙烷 、 5-Hydroxy-2-(4-methoxyphenyl)-1-benzofuran-4-carbaldehyde 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from ortho-Vinylaryl Akyl Ethers

  摘要：

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).

  DOI：

  10.1021/ol900915p
• 作为产物：
  描述：

  4-乙炔基苯甲醚 、 2-溴-3,6-二羟基苯甲醛 在 三乙胺 、 乙酰氯 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 tris[tert-butyl]phosphonium tetrafluoroborate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.08h， 以63%的产率得到5-Hydroxy-2-(4-methoxyphenyl)-1-benzofuran-4-carbaldehyde
  参考文献：
  名称：

  C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from ortho-Vinylaryl Akyl Ethers

  摘要：

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).

  DOI：

  10.1021/ol900915p

文献信息

• [EN] NOVEL COMPOUNDS AND COMPOSITIONS USED AS ANTICANCER AGENTS<br/>[FR] NOUVEAUX COMPOSES ET COMPOSITIONS UTILISES COMME ANTICANCEREUX
  申请人：UNIV PARIS DIDEROT PARIS 7

  公开号：WO2013114040A1

  公开（公告）日：2013-08-08

  La présente invention concerne de nouveaux composés organiques, leur procédé de synthèse, et leurs utilisations notamment dans le domaine du traitement du cancer. En particulier, la présente invention concerne de nouveaux composés anticancéreux, notamment des composés capables d'inhiber l'enzyme mTOR (marmalian target of rapamycine)de manière efficace. L'invention concerne également des compositions pharmaceutiques ou non pharmaceutiques comportant lesdits composés.
• C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from <i>ortho</i>-Vinylaryl Akyl Ethers
  作者：Kevin M. McQuaid、Jonathan Z. Long、Dalibor Sames

  DOI：10.1021/ol900915p

  日期：2009.7.16

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).