dimethyl 3-acetylcyclopent-3-ene-1,1-dicarboxylate | 172538-85-1

• 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-acetylcyclopent-3-ene-1,1-dicarboxylate
• 英文别名: Dimethyl 3-acetylcyclopent-3-ene-1,1-dicarboxylate
• CAS: 172538-85-1
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: DFLDSWZTTCSASY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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

• 作为反应物：
  描述：

  三氟甲磺酸三甲基硅酯 、 dimethyl 3-acetylcyclopent-3-ene-1,1-dicarboxylate 、 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Stereoselective Multiple Functionalization of Pyrylium Salts by Domino Reactions with 2-Silyloxybuta-1,3-dienes

  摘要：

  Six at a time! Up to six stereogenic centers can be diastereoselectively formed in one step in three-component domino reactions of 4-silyloxypyrylium triflates with 2-silyloxybuta-1,3-dienes. Annulated or bridged ring systems such as 1 and 2, respectively, can be formed with high selectivity. R1 =silyl group; R2 , R3 =organyl group.

  DOI：

  10.1002/1521-3773(20010202)40:3<568::aid-anie568>3.0.co;2-l
• 作为产物：
  描述：

  dimethyl 2-(but-2-ynyl)-2-(formylmethyl)malonate 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 溶剂黄146 作用下， 反应 24.0h， 以40%的产率得到dimethyl 3-acetylcyclopent-3-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Ru-Catalyzed Cyclization of Terminal Alkynals to Cycloalkenes

  摘要：

  Cycloalkenes can be efficiently prepared by a new Ru-catalyzed cyclization of terminal alkynals. Under appropriate conditions, cycloisomerizations to conjugated aldehydes may be observed. Both processes involve catalytic Ru vinylidenes.

  DOI：

  10.1021/ja0610434

文献信息

• Ru-Catalyzed Cyclization of Terminal Alkynals to Cycloalkenes
  作者：Jesús A. Varela、Carlos González-Rodríguez、Silvia G. Rubín、Luis Castedo、Carlos Saá

  DOI：10.1021/ja0610434

  日期：2006.8.1

  Cycloalkenes can be efficiently prepared by a new Ru-catalyzed cyclization of terminal alkynals. Under appropriate conditions, cycloisomerizations to conjugated aldehydes may be observed. Both processes involve catalytic Ru vinylidenes.
• Stereoselective Multiple Functionalization of Pyrylium Salts by Domino Reactions with 2-Silyloxybuta-1,3-dienes
  作者：Uwe Beifuss、Kim Goldenstein、Frank Döring、Christopher Lehmann、Mathias Noltemeyer

  DOI：10.1002/1521-3773(20010202)40:3<568::aid-anie568>3.0.co;2-l

  日期：2001.2.2

  Six at a time! Up to six stereogenic centers can be diastereoselectively formed in one step in three-component domino reactions of 4-silyloxypyrylium triflates with 2-silyloxybuta-1,3-dienes. Annulated or bridged ring systems such as 1 and 2, respectively, can be formed with high selectivity. R1 =silyl group; R2 , R3 =organyl group.
• 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.

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