2,4-dimethyl-7,11-diphenyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone | 62163-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-dimethyl-7,11-diphenyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone
• 英文别名: (7R,11S)-2,4-dimethyl-7,11-diphenyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetrone
• CAS: 62163-48-8
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: NOSQTNLUUNHXBI-KDURUIRLSA-N

物化性质

• 沸点：
  564.2±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-7,11-diphenyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone 在 亚硝基苯 、 L-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以71%的产率得到(7S,8R,11R)-8-hydroxy-2,4-dimethyl-7,11-diphenyl-2,4-diaza-spiro[5.5]undecane-1,3,5,9-tetraone
  参考文献：
  名称：

  Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of meso-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions

  摘要：

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.

  DOI：

  10.1021/ol050246e
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 二苄叉丙酮 在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到2,4-dimethyl-7,11-diphenyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone
  参考文献：
  名称：

  二氢嘧啶衍生物的合成，体外生物学活性和计算机模拟研究。

  摘要：

  我们在这里描述了二氢嘧啶衍生物3a-p的合成及其α-葡萄糖苷酶抑制活性的评估。化合物3b（IC50 = 62.4±1.5μM），3c（IC50 = 25.3±1.26μM），3d（IC50 = 12.4±0.15μM），3e（IC50 = 22.9±0.25μM），3g（IC50 = 23.8±0.17μM） ，3h（IC50 = 163.3±5.1μM），3i（IC50 = 30.6±0.6μM），3m（IC50 = 26.4±0.34μM）和3o（IC50 = 136.1±6.63μM）被发现是有效的α-葡萄糖苷酶抑制剂。与标准药物阿卡波糖（IC50 = 840±1.73μM）相比。还评估了这些化合物对PC-3，HeLa和MCF-3癌细胞系以及3T3小鼠成纤维细胞系的体外细胞毒活性。除化合物3f和3m（IC50 = 17.79±0.66-20.44±0.30μM）（对HeLa和3T3细

  DOI：

  10.1016/j.bmc.2015.09.001

文献信息

• An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction
  作者：Komal Aggarwal、Kanika Vij、Jitender M. Khurana

  DOI：10.1039/c4ra00521j

  日期：——

  2,4-Diazaspiro[5.5]undecane-1,3,5,9-tetraones and 3-thioxo-2,4-diazaspiro[5.5]undecane-1,5,9-triones have been synthesized via double Michael addition of 1,5-diaryl-1,4-pentadien-3-one with active methylene compounds such as N,N-dimethyl barbituric acid, barbituric acid, thio-barbituric acid and N,N-diphenyl thiobarbituric acid in ethylene glycol at 100 °C in the absence of any catalyst to give high yields within a short reaction time. The structure has been confirmed by X-ray analysis. The single-crystal structure of the diazaspiro compound revealed that the CAr–H⋯π, π–π stacking and intermolecular hydrogen bonding interactions act as major driving forces for crystal packing.

  通过1,5-二芳基-1,4-戊二烯-3-酮与活性甲烷化合物（如N,N-二甲基巴比妥酸、巴比妥酸、硫代巴比妥酸和N,N-二苯基硫代巴比妥酸）在100°C的无催化剂乙二醇中进行双迈克尔加成反应，合成了一系列2,4-二氮杂螺[5.5]十一烷-1,3,5,9-四酮和3-硫代-2,4-二氮杂螺[5.5]十一烷-1,5,9-三酮，产率高且反应时间短。结构通过X射线分析得到确认。二氮杂螺化合物的单晶结构揭示，CAr–H⋯π、π–π堆积和分子间氢键相互作用是晶体堆积的主要驱动力。
• Development of drug intermediates by using direct organocatalytic multi-component reactions
  作者：Dhevalapally B. Ramachary、M. Kishor、G. Babul Reddy

  DOI：10.1039/b602696f

  日期：——

  Novel, economic and environmentally friendly one-pot three-component Knoevenagel/hydrogenation (K/H) and four-component Knoevenagel/hydrogenation/alkylation (K/H/A) reactions of ketones, CH-acids, dihydropyridines and alkyl halides using proline and proline/metal carbonate catalysis, respectively, have been developed. Many of the products of these K/H and K/H/A reactions have direct applications in pharmaceutical chemistry.

  新颖、经济且环境友好的一锅法三组分Knoevenagel/氢化（K/H）和四组分Knoevenagel/氢化/烷基化（K/H/A）反应已被开发，这些反应分别使用脯氨酸和脯氨酸/金属碳酸盐作为催化剂，涉及酮类、CH-酸类、二氢吡啶类及卤代烷类物质。这些K/H和K/H/A反应的许多产物在药物化学领域具有直接应用价值。
• Development of Pharmaceutical Drugs, Drug Intermediates and Ingredients by Using Direct Organo-Click Reactions
  作者：Dhevalapally B. Ramachary、Mamillapalli Kishor、Y. Vijayendar Reddy

  DOI：10.1002/ejoc.200701014

  日期：2008.2

  two-carbon homologation through cascade O/H/H reactions of aldehydes 1, Meldrum's acid (3c), Hantzsch ester (4) and acetic acid/triethylamine in ethanol has been demonstrated. Additionally, we have developed a green synthesis of the highly substituted 1,2,3-triazole 17 from simple substrates through a two-step combination of olefination/hydrogenation/alkylation and Huisgen cycloaddition reaction sequences

  在这里，我们报告了我们使用氨基酸、胺、K2CO3 或 Cs2CO3 和 CuSO4/Cu 的组合来催化绿色级联反应的研究。我们的目标是在非常温和和环境友好的条件下制备高反应性和取代的烯烃物质 7 和 8，从而通过降低 HOMO-LUMO 的自催化作用，通过 Hantzsch 酯 (4) 的作用得到氢化产物 10 和 12通过仿生还原，烯烃 7/8 和 Hantzsch 酯 (4) 之间的能隙。非常有用的化合物 10 到 14 由简单的底物如醛 1、酮 2、CH 酸 3、Hantzsch 酯 (4) 和卤代烷 5 通过涉及级联烯化/氢化 (O/H) 的面向多样性的绿色合成组装而成，烯烃化/氢化/烷基化 (O/H/A) 和氢化/烯烃化/氢化 (H/O/H) 反应序列以一锅法与立体定向有机碳酸盐和有机/金属碳酸盐催化。高度官能化的多种化合物，例如 10 至 14，是具有生物活性的产品，已广泛应用
• Synthesis, in vitro biological activities and in silico study of dihydropyrimidines derivatives
  作者：Assem Barakat、Mohammad Shahidul Islam、Abdullah Mohammed Al-Majid、Hazem A. Ghabbour、Hoong-Kun Fun、Kulsoom Javed、Rehan Imad、Sammer Yousuf、M. Iqbal Choudhary、Abdul Wadood

  DOI：10.1016/j.bmc.2015.09.001

  日期：2015.10

  evaluated for their in vitro cytotoxic activity against PC-3, HeLa, and MCF-3 cancer cell lines, and 3T3 mouse fibroblast cell line. All compounds were found to be non cytotoxic, except compounds 3f and 3m (IC50=17.79±0.66-20.44±0.30 μM), which showed a weak cytotoxic activity against the HeLa, and 3T3 cell lines. In molecular docking simulation study, all the compounds were docked into the active site

  我们在这里描述了二氢嘧啶衍生物3a-p的合成及其α-葡萄糖苷酶抑制活性的评估。化合物3b（IC50 = 62.4±1.5μM），3c（IC50 = 25.3±1.26μM），3d（IC50 = 12.4±0.15μM），3e（IC50 = 22.9±0.25μM），3g（IC50 = 23.8±0.17μM） ，3h（IC50 = 163.3±5.1μM），3i（IC50 = 30.6±0.6μM），3m（IC50 = 26.4±0.34μM）和3o（IC50 = 136.1±6.63μM）被发现是有效的α-葡萄糖苷酶抑制剂。与标准药物阿卡波糖（IC50 = 840±1.73μM）相比。还评估了这些化合物对PC-3，HeLa和MCF-3癌细胞系以及3T3小鼠成纤维细胞系的体外细胞毒活性。除化合物3f和3m（IC50 = 17.79±0.66-20.44±0.30μM）（对HeLa和3T3细
• Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of <i>meso</i>-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions
  作者：Dhevalapally B. Ramachary、Carlos F. Barbas

  DOI：10.1021/ol050246e

  日期：2005.4.14

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.