2(3H)-Furanone, 3,3'-(1,4-piperazinediyl)bis[dihydro- | 139605-63-3

• 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: 2(3H)-Furanone, 3,3'-(1,4-piperazinediyl)bis[dihydro-
• 英文别名: 3-[4-(2-oxooxolan-3-yl)piperazin-1-yl]oxolan-2-one
• CAS: 139605-63-3
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: PJBYRWFNPMADRH-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2(3H)-Furanone, 3,3'-(1,4-piperazinediyl)bis[dihydro- 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以100%的产率得到
  参考文献：
  名称：

  Synthesis, Conformation and Equilibrium Study of New Piperazine and Azamacrocyclic Ligands with N-(Tetrahydro-2-oxofuran-3-yl) and N-[(Carboxy)(2-hydroxyethyl)methyl] Pendant Arms

  摘要：

  New piperazine (1), homopiperazine (2), 1-tosyl-1,4,7-triazacyclononane (3), 1,4,7-triazacyclononane (4), and 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (5) derivatives 1a-5a with 2-oxotetrahydrofuran-3-yl pendant arms have been synthesized from the parent cyclic polyamines 1-5 and 2-bromobutyrolactone in acetonitrile. Their conformational properties have been studied by molecular mechanics and NMR spectroscopy, and new sets of Karplus parameters for calculation of the vicinal coupling constants of the butyrolactone moieties have been determined. Compounds 1a-5a were hydrolysed to (carboxy)(2-hydroxyethyl)methyl derivatives 1b-5b by treatment with aqueous sodium hydroxide. The protonation and complexation properties of 4b (HOET-NOTA) were studied by pH potentiometry, photometry, and H-1 NMR titrations, and the results were compared with the corresponding values for NOTA. It was found that, although complexation of 4b with smaller metal ions was approximately two orders of magnitude weaker, its stability constants with the lanthanides remained unchanged.

  DOI：

  10.1002/1099-0690(20021)2002:2<351::aid-ejoc351>3.0.co;2-6
• 作为产物：
  描述：

  哌嗪 、 α-溴-γ-丁内酯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以65%的产率得到2(3H)-Furanone, 3,3'-(1,4-piperazinediyl)bis[dihydro-
  参考文献：
  名称：

  Synthesis, Conformation and Equilibrium Study of New Piperazine and Azamacrocyclic Ligands with N-(Tetrahydro-2-oxofuran-3-yl) and N-[(Carboxy)(2-hydroxyethyl)methyl] Pendant Arms

  摘要：

  New piperazine (1), homopiperazine (2), 1-tosyl-1,4,7-triazacyclononane (3), 1,4,7-triazacyclononane (4), and 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (5) derivatives 1a-5a with 2-oxotetrahydrofuran-3-yl pendant arms have been synthesized from the parent cyclic polyamines 1-5 and 2-bromobutyrolactone in acetonitrile. Their conformational properties have been studied by molecular mechanics and NMR spectroscopy, and new sets of Karplus parameters for calculation of the vicinal coupling constants of the butyrolactone moieties have been determined. Compounds 1a-5a were hydrolysed to (carboxy)(2-hydroxyethyl)methyl derivatives 1b-5b by treatment with aqueous sodium hydroxide. The protonation and complexation properties of 4b (HOET-NOTA) were studied by pH potentiometry, photometry, and H-1 NMR titrations, and the results were compared with the corresponding values for NOTA. It was found that, although complexation of 4b with smaller metal ions was approximately two orders of magnitude weaker, its stability constants with the lanthanides remained unchanged.

  DOI：

  10.1002/1099-0690(20021)2002:2<351::aid-ejoc351>3.0.co;2-6

文献信息

• Synthesis, Conformation and Equilibrium Study of New Piperazine and Azamacrocyclic Ligands with N-(Tetrahydro-2-oxofuran-3-yl) and N-[(Carboxy)(2-hydroxyethyl)methyl] Pendant Arms
  作者：István Lázár、Adél Egri、Róbert Király、Zsolt Baranyai、Tímea Iványi、Ernő Brücher

  DOI：10.1002/1099-0690(20021)2002:2<351::aid-ejoc351>3.0.co;2-6

  日期：2002.1

  New piperazine (1), homopiperazine (2), 1-tosyl-1,4,7-triazacyclononane (3), 1,4,7-triazacyclononane (4), and 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (5) derivatives 1a-5a with 2-oxotetrahydrofuran-3-yl pendant arms have been synthesized from the parent cyclic polyamines 1-5 and 2-bromobutyrolactone in acetonitrile. Their conformational properties have been studied by molecular mechanics and NMR spectroscopy, and new sets of Karplus parameters for calculation of the vicinal coupling constants of the butyrolactone moieties have been determined. Compounds 1a-5a were hydrolysed to (carboxy)(2-hydroxyethyl)methyl derivatives 1b-5b by treatment with aqueous sodium hydroxide. The protonation and complexation properties of 4b (HOET-NOTA) were studied by pH potentiometry, photometry, and H-1 NMR titrations, and the results were compared with the corresponding values for NOTA. It was found that, although complexation of 4b with smaller metal ions was approximately two orders of magnitude weaker, its stability constants with the lanthanides remained unchanged.