7,9-二氧代-8-氮杂螺[4.5]癸烷-6,10-二甲腈 | 42940-56-7

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 7,9-二氧代-8-氮杂螺[4.5]癸烷-6,10-二甲腈
• 中文别名: 7,9-二氧-8-氮杂螺(4.5)癸6,10-二氰基戊烷
• 英文名称: 7,9-dioxo-8-azaspiro[4.5]decane-6,10-dicarbonitrile
• 英文别名: 6,10-dicyano-8-azaspiro[4,5]decane-7,9-dione；7,9-dioxo-8-aza-spiro[4.5]decane-6,10-dicarbonitrile；7,9-Dioxo-8-aza-spiro[4.5]decan-6,10-dicarbonitril
• CAS: 42940-56-7
• 化学式: C₁₁H₁₁N₃O₂
• mdl: MFCD00012103
• 分子量: 217.227
• InChiKey: USIMPDHJLHKMKA-UHFFFAOYSA-N

物化性质

• 熔点：
  182-185 °C(lit.)
• 沸点：
  558.2±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  7,9-二氧代-8-氮杂螺[4.5]癸烷-6,10-二甲腈 在 硫酸 作用下， 以81%的产率得到spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nonane)]-2',4',6',8'-tetraone
  参考文献：
  名称：

  Synthesis, Pharmacological Characterization, and Quantitative Structure−Activity Relationship Analyses of 3,7,9,9-Tetraalkylbispidines:  Derivatives with Specific Bradycardic Activity

  摘要：

  A series of 3,7,9,9-tetraalkyl-3,7-diazabicyclo[3.3.1]nonane derivatives (bispidines) was synthesized and identified as potential antiischemic agents. Pharmacological experiments in vitro as well as in vivo are described, and the results are listed. For selection of those compounds fitting best to the desired profile of a specific bradycardic antianginal agent-decrease in heart rate without affecting contractility and blood pressure-these results were scored and ranked. Quantitative structure-activity relationship (QSAR) analyses were performed and discussed a posteriori by means of Hansch, nonelementary discriminant and factor analysis to get insight into the molecular features determining the biological profile. Highly significant equations were obtained, indicating hydrophobic and steric effects. Both pharmacological ranking and QSAR considerations showed compound 6 as the optimum within the structural class under investigation. Compound 6 (tedisamil, KC8857) has been selected as the most promising compound and was chosen for further pharmacological and clinical investigations as an antiischemic drug.

  DOI：

  10.1021/jm970120q
• 作为产物：
  描述：

  环戊酮 、 氰乙酸乙酯 在 甲醇 、 氮化锂 作用下， 反应 14.0h， 以82%的产率得到7,9-二氧代-8-氮杂螺[4.5]癸烷-6,10-二甲腈
  参考文献：
  名称：

  使用氮化锂作为氨的方便来源合成 4-取代的 3,5-二氰基-2,6-哌啶二酮

  摘要：

  通过醛或酮、氰基乙酸乙酯、氮化锂 (Li 3 N) 的三组分反应，以良好的收率实现了简单高效的一锅法合成 4-取代-3,5-二氰基-2,6-哌啶二酮作为 MeOH 中氨的方便来源。

  DOI：

  10.3987/com-08-11584

文献信息

• Chemical and electrocatalytic cascade cyclization of Guareschi imides: ‘one-pot’ simple and efficient way to the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold
  作者：Anatoly N. Vereshchagin、Michail N. Elinson、Evgeniya O. Dorofeeva、Dmitry V. Demchuk、Ivan S. Bushmarinov、Alexander S. Goloveshkin、Gennady I. Nikishin

  DOI：10.1016/j.tet.2013.04.035

  日期：2013.6

  as mediator results in fast and efficient cyclization with formation of a substituted 3-azabicyclo[3.1.0]hexane system in 80–98%. The fast (30 min) electrocatalytic reaction proceeds smoothly under neutral and mild conditions. The use of electrocatalysis in a cascade cyclization reaction is an efficient approach to the medicinally relevant 3-azabicyclo[3.1.0]hexane scaffold avoiding the inconvenient

  在存在溴化钠作为介体的情况下，在未分裂的细胞中，瓜尔基酰亚胺在乙醇中的电解可快速有效地环化，形成80-98％的取代的3-氮杂双环[3.1.0]己烷系统。快速（30分钟）的电催化反应在中性和温和条件下平稳进行。在级联环化反应中使用电催化是医学上有用的3-氮杂双环[3.1.0]己烷骨架的有效方法，避免了分子卤素或卤代底物直接使用的不便，并且从多样性导向的角度出发也是有益的大规模的过程。
• Kon; Thorpe, Journal of the Chemical Society, 1919, vol. 115, p. 702
  作者：Kon、Thorpe

  DOI：——

  日期：——
• Birch; Thorpe, Journal of the Chemical Society, 1922, vol. 121, p. 1835
  作者：Birch、Thorpe

  DOI：——

  日期：——
• Paul, Journal of the Indian Chemical Society, 1931, vol. 8, p. 717,723
  作者：Paul

  DOI：——

  日期：——
• Antiproliferative and antibacterial activity of some glutarimide derivatives
  作者：Jelena B. Popović-Djordjević、Anita S. Klaus、Željko S. Žižak、Ivana Z. Matić、Branko J. Drakulić

  DOI：10.3109/14756366.2015.1070844

  日期：2016.11.1

  Antiproliferative and antibacterial activities of nine glutarimide derivatives (1-9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11] heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9-27 mu M). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6-8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl) butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 x 10(-3) mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.