5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone | 257883-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone
• 英文别名: 2-(1H-inden-2-yl)-5,5-dimethylpyrazolidin-3-one
• CAS: 257883-12-8
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: ILVHGOIPNDQKPM-UHFFFAOYSA-N

物化性质

• 沸点：
  343.0±52.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone 以 乙醇 为溶剂， 反应 4.0h， 以41%的产率得到rel-(7aR,12aS)-6,7-bis(methoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-one
  参考文献：
  名称：

  Unusual Reactions of 5,5-Dimethyl-2-(indenyl-2)-3-pyrazolidinone with Acetylenedicarboxylates

  摘要：

  [GRAPHICS]Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2 substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis (alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products.

  DOI：

  10.1021/ol9911829
• 作为产物：
  描述：

  5,5-二甲基吡唑啉-3-酮 、 2-茚酮 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone
  参考文献：
  名称：

  Unusual Reactions of 5,5-Dimethyl-2-(indenyl-2)-3-pyrazolidinone with Acetylenedicarboxylates

  摘要：

  [GRAPHICS]Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2 substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis (alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products.

  DOI：

  10.1021/ol9911829

文献信息

• Unusual Reactions of 5,5-Dimethyl-2-(indenyl-2)-3-pyrazolidinone with Acetylenedicarboxylates
  作者：Cvetka Turk、Jurij Svete、Branko Stanovnik、Ljubo Golič、Amalija Golobič、Lovro Selič

  DOI：10.1021/ol9911829

  日期：2000.2.1

  [GRAPHICS]Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2 substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis (alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products.