2,4-bis(4-chlorophenyl)-2,4-diazaspiro[5.5]undecan-7-one | 1399545-00-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,4-bis(4-chlorophenyl)-2,4-diazaspiro[5.5]undecan-7-one
• 英文别名: 2,4-Bis(4-chlorophenyl)-2,4-diazaspiro[5.5]undecan-11-one；2,4-bis(4-chlorophenyl)-2,4-diazaspiro[5.5]undecan-11-one
• CAS: 1399545-00-6
• 化学式: C₂₁H₂₂Cl₂N₂O
• 分子量: 389.324
• InChiKey: IMHQTQLQJWGNAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-乙酰基环己酮 、 对氯苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 3.17h， 以61%的产率得到2,4-bis(4-chlorophenyl)-2,4-diazaspiro[5.5]undecan-7-one
  参考文献：
  名称：

  One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

  摘要：

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

  DOI：

  10.1055/s-0033-1339922

文献信息

• CuFe2O4 nanoparticles as a highly efficient and magnetically recoverable catalyst for the synthesis of medicinally privileged spiropyrimidine scaffolds
  作者：Anshu Dandia、Anuj K. Jain、Sonam Sharma

  DOI：10.1039/c2ra22477a

  日期：——

  A highly efficient and green protocol for the synthesis of medicinally important fluorinated spiropyrimidine derivatives involving creation of six new covalent bonds has been developed using a magnetically separable and reusable heterogeneous copper ferrite nanocatalyst under mild reaction conditions. The synthesis of inverse spinel copper ferrite magnetic nanoparticles with average size of 38 nm has been achieved using combined sonochemical and co-precipitation techniques in aqueous medium from readily available inexpensive starting materials without any surfactant or capping agent. The particle size was determined by transmission electron microscopy (TEM), scanning electron microscopy (SEM) and X-ray diffraction (XRD) analysis. The magnetic nature of catalyst facilitates its easy removal from the reaction medium and can be reused five times without any significant loss of its catalytic activity. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign. The structure of final products was established by single crystal X-ray analysis and spectroscopic techniques.

  开发了一种高效绿色的合成重要药用氟化螺嘧啶衍生物的协议，该协议涉及在温和反应条件下使用磁性可分离和可重复使用的异质铜铁氧体纳米催化剂创造六个新的共价键。通过在水性介质中结合声化学和共沉淀技术，从易于获取的廉价起始材料中，无需任何表面活性剂或配体，实现了反尖晶石铜铁氧体磁性纳米粒子的合成，平均粒径为38 nm。粒径通过透射电子显微镜（TEM）、扫描电子显微镜（SEM）和X射线衍射（XRD）分析确定。催化剂的磁性质使其易于从反应介质中去除，并且可以重复使用五次而不显著损失其催化活性。在连续循环中Cu和Fe的渗出可以忽略不计，使得催化剂经济且环境友好。最终产品的结构通过单晶X射线分析和光谱技术确定。
• Metal free green protocol for the synthesis of bis-spiro piperidine and pyrimidine derivatives
  作者：Audumbar Patil、Rajashri Salunkhe

  DOI：10.1007/s11164-018-3310-7

  日期：2018.5

  one-pot three-component synthesis of bis-spiro piperidine and pyrimidine derivatives has been reported by performing the reaction of formaldehyde, aromatic aniline and 1,3-dicarbonyl compounds. This reaction was carried out at room temperature in 2,2,2-trifluoroethanol (TFE) as a recyclable reaction medium under the metal free condition. The strong hydrogen donor ability and acidic property of TFE plays

  摘要 据报道，通过甲醛，芳族苯胺和1,3-二羰基化合物的反应，可以高效地一锅三组分合成双螺哌啶和嘧啶衍生物。该反应在室温下在2,2,2-三氟乙醇（TFE）中作为可循环的反应介质在无金属条件下进行。TFE的强大的氢供体能力和酸性对加快反应速率和平稳引发反应起着关键作用。该方法的优点是反应条件温和，无需柱色谱纯化，产物收率高和TFE可回收利用。 图形概要
• Dy/chitosan: a highly efficient and recyclable heterogeneous nano catalyst for the synthesis of hexahydropyrimidines in aqueous media
  作者：Nayeem Ahmed、Saima Tarannum、Zeba N. Siddiqui

  DOI：10.1039/c5ra08160b

  日期：——

  Dy(iii)/chitosan as a recyclable and heterogeneous catalyst is used for the sustainable preparation of hexahydropyrimidine derivatives in aqueous media.

  Dy（iii）/壳聚糖作为可回收和杂化催化剂，用于在水性介质中可持续制备六氢嘧啶衍生物。
• Indium triflate catalyzed one-pot multicomponent synthesis of spiro-hexahydropyrimidines explained by multiple covalent bond formation
  作者：Anshu Dandia、Anuj K. Jain、Sonam Sharma

  DOI：10.1016/j.tetlet.2012.07.079

  日期：2012.9

  A mild, efficient, and expeditious method has been developed for the synthesis of spiro-hexahydropyrimidine derivatives via a three-component, one-pot cyclocondensation reaction of aromatic amines, formaldehyde, and cyclic ketones in 4-6 h using In(OTf)(3) as Lewis acid catalyst for the first time. The reaction involving creation of six new covalent bonds was efficiently promoted by 10 mol % In(OTf)(3) and the catalyst could be recovered easily after the reaction and reused without any loss of its catalytic activity. The advantageous features of this methodology are high atom-economy, operational simplicity, shorter reaction time, and easy handling. (c) 2012 Elsevier Ltd. All rights reserved.
• One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines
  作者：Julia Stephanidou-Stephanatou、Constantinos Tsoleridis、Constantinos Neochoritis、Nicolaos Eleftheriadis、Arianna Tsiantou

  DOI：10.1055/s-0033-1339922

  日期：——

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.