dimethyl 2,2-dimethyl-4H-chromene-3,3-dicarboxylate | 1173178-76-1

• 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: dimethyl 2,2-dimethyl-4H-chromene-3,3-dicarboxylate
• CAS: 1173178-76-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: UWHMTYWSUFDGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-Isopropoxy phenyl-methylene-propanedioic acid dimethyl ester 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到dimethyl 2,2-dimethyl-4H-chromene-3,3-dicarboxylate
  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

• 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).