dimethyl 3-formylcyclohex-3-ene-1,1-dicarboxylate | 906652-80-0

• 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: dimethyl 3-formylcyclohex-3-ene-1,1-dicarboxylate
• 英文别名: Dimethyl 3-formylcyclohex-3-ene-1,1-dicarboxylate
• CAS: 906652-80-0
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: KKMPDAGRQOXHGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  1,3-dimethyl 2-(3-oxopropyl)-2-(prop-2-yn-1-yl)malonate 在 三氟乙酸 作用下， 反应 24.0h， 以27%的产率得到dimethyl 3-formyl-4-methylcyclopent-3-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones

  摘要：

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.

  DOI：

  10.1021/ol900142r

文献信息

• Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones
  作者：Carlos González-Rodríguez、Luz Escalante、Jesús A. Varela、Luis Castedo、Carlos Saá

  DOI：10.1021/ol900142r

  日期：2009.4.2

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.