diethyl 6H-5-formyl-5-methylindan-2,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 6H-5-formyl-5-methylindan-2,2-dicarboxylate
• 英文别名: diethyl 6-formyl-6-methyl-3,5-dihydro-1H-indene-2,2-dicarboxylate
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: ZSLDKINAFSHRFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基丙烯醛 、 diethyl 5-acetylindan-2,2-dicarboxylate 在 nickel dichloride 、 锌 三乙胺 、 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到diethyl 6H-5-formyl-5-methylindan-2,2-dicarboxylate
  参考文献：
  名称：

  Nickel- and Zinc-Promoted [2 + 2 + 2] Cycloaddition of Diynes and α,β-Enones

  摘要：

  The [2 + 2 + 2] cycloaddition of diynes and enones occurred in the presence of both nickel and zinc together. This binary metal-mediated reaction had two interesting features: (1) a terminally unsubstituted diyne reacted with an enone to give an aromatic compound with the concomitant incorporation of two hydrogen atoms abstracted from an expected 1,S-diene product into another molecule of the starting enone and (2) a trimethylsilyl-substituted diyne reacted with an equimolar amount of enone to regioselectively afford a 1,3-diene, in which the trimethylsilyl group is adjacent to the carbonyl group.

  DOI：

  10.1021/jo980987b

文献信息

• Nickel- and Zinc-Promoted [2 + 2 + 2] Cycloaddition of Diynes and α,β-Enones
  作者：Shin-ichi Ikeda、Hitomi Watanabe、Yoshiro Sato

  DOI：10.1021/jo980987b

  日期：1998.10.1

  The [2 + 2 + 2] cycloaddition of diynes and enones occurred in the presence of both nickel and zinc together. This binary metal-mediated reaction had two interesting features: (1) a terminally unsubstituted diyne reacted with an enone to give an aromatic compound with the concomitant incorporation of two hydrogen atoms abstracted from an expected 1,S-diene product into another molecule of the starting enone and (2) a trimethylsilyl-substituted diyne reacted with an equimolar amount of enone to regioselectively afford a 1,3-diene, in which the trimethylsilyl group is adjacent to the carbonyl group.