2-(2,4-dioxopentyl)isoindoline-1,3-dione | 412033-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2,4-dioxopentyl)isoindoline-1,3-dione
• 英文别名: N-(2,4-dioxo-pentyl)-phthalimide；N-(2,4-Dioxo-pentyl)-phthalimid；1,3-Isoindolinedione, 2-(2,4-dioxopentyl)；2-(2,4-dioxopentyl)isoindole-1,3-dione
• CAS: 412033-37-5
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: BXZJQMPHLFGJME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dioxopentyl)isoindoline-1,3-dione 在 乙醇 、 一水合肼 作用下， 反应 4.0h， 生成 sulfanilic acid-(5-methyl-1(2)H-pyrazol-3-ylmethylamide)
  参考文献：
  名称：

  1-Phthalimidopentane-2：4-dione

  摘要：

  DOI：

  10.1039/jr9540004548
• 作为产物：
  描述：

  N-邻苯二甲酰甘氨酰氯 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(2,4-dioxopentyl)isoindoline-1,3-dione
  参考文献：
  名称：

  钌在邻近杂原子的辅助下催化β-二酮的化学和对映选择性加氢

  摘要：

  通过使用[Ru（苯）（S）-SunPhosCl] Cl在THF中的稠度，可以实现β-二酮的高度化学和对映选择性氢化。相邻的杂原子在保证反应性和控制化学选择性方面起着重要作用。这些结果暗示了清洁和容易地合成官能化的手性β-羟基酮的潜在方法，该方法可以通过少得多的步骤经济转化来制备。

  DOI：

  10.1021/acs.orglett.9b01829

文献信息

• Synthesis and Structure–Activity Relationship (SAR) of (5,7-Disubstituted 3-phenylsulfonyl-pyrazolo[1,5-<i>a</i>]pyrimidin-2-yl)-methylamines as Potent Serotonin 5-HT₆ Receptor (5-HT₆R) Antagonists
  作者：Alexandre V. Ivachtchenko、Elena S. Golovina、Madina G. Kadieva、Volodymyr M. Kysil、Oleg D. Mitkin、Sergey E. Tkachenko、Ilya M. Okun

  DOI：10.1021/jm201079g

  日期：2011.12.8

  Syntheses, biological evaluation as 5-HT6 receptor (5-HT6R) antagonists, and structure activity relationships for a series of novel 5,7-disubstituted (3-arylsulfonyl-pyrazolo[1,5-a]pyrimidins are disclosed. The molecule conformational flexibility in the series is restricted by formation of the intramolecular hydrogen bond between 3-sulfo and 2-methylamino groups, which renders high potency and high selectivity to block serotonin-induced responses in HEK-293 cells stably expressing human 5-HT6R. In this work, we tested the hypothesis if addition of a positively ionizable group (PI) to the pyrimidine ring of the scaffold members in positions 5, 6, or 7 could further increase their 5HT(6)R blocking potency. We show that the presence of the PI group with small substituents does not substantially affect either potency or selectivity of the ligands while causing substantial changes in their cLogP values. This provides a possibility for designing of the 5HT(6)R ligands with modified ADME characteristics without grossly affecting efficiency of their interaction with the receptor. In respect to the structure-activity relationship (SAR), among other physiochemical parameters, only the molecule size and shape (described by gyration radii) showed a clear tendency for more compact molecules to be more potent antagonists of this receptor.
• Ru-Catalyzed Chemo- and Enantioselective Hydrogenation of β-Diketones Assisted by the Neighboring Heteroatoms
  作者：Wanfang Li、Bin Lu、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.orglett.9b01829

  日期：2019.7.19

  A highly chemo- and enantioselective hydrogenation of β-diketones was achieved by using [Ru(benzene)(S)-SunPhosCl]Cl for consistency in THF. The neighboring heteroatoms played important roles in guaranteeing the reactivity and controlling the chemoselectivity. These results suggested a potential approach for the clean and facile synthesis of functionalized chiral β-hydroxy ketones, which could otherwise

  通过使用[Ru（苯）（S）-SunPhosCl] Cl在THF中的稠度，可以实现β-二酮的高度化学和对映选择性氢化。相邻的杂原子在保证反应性和控制化学选择性方面起着重要作用。这些结果暗示了清洁和容易地合成官能化的手性β-羟基酮的潜在方法，该方法可以通过少得多的步骤经济转化来制备。
• 1-Phthalimidopentane-2 : 4-dione
  作者：R. E. Bowman、D. J. Tivey

  DOI：10.1039/jr9540004548

  日期：——