7-chloro-3,4-dihydro-3,3-dimethylacridin-1(2H)-one | 1431472-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-chloro-3,4-dihydro-3,3-dimethylacridin-1(2H)-one
• 英文别名: 7-chloro-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one；7-Chloro-3,4-dihydro-3,3-dimethylacridin-1(2h)-one；7-chloro-3,3-dimethyl-2,4-dihydroacridin-1-one
• CAS: 1431472-21-7
• 化学式: C₁₅H₁₄ClNO
• 分子量: 259.735
• InChiKey: NVMXIGVIVXLHDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 对苯醌 作用下， 以100%的产率得到7-chloro-3,4-dihydro-3,3-dimethylacridin-1(2H)-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

• Eco-Friendly Catalytic Systems Based on Carbon-Supported Magnesium Oxide Materials for the Friedländer Condensation
  作者：Marina Godino-Ojer、Antonio J. López-Peinado、Rosa M. Martín-Aranda、Jacek Przepiórski、Elena Pérez-Mayoral、Elena Soriano

  DOI：10.1002/cctc.201402602

  日期：2014.12

  Carbon‐supported MgO materials are excellent and sustainable catalysts for the synthesis of N‐containing heterocyclic compounds by the Friedländer condensation under mild, solvent‐free conditions. The results reported herein indicate that MgO is the most active catalytic species that accelerates the reaction compared with the catalytic behavior observed for the carbon material Norit RX3. On the basis

  碳载MgO材料是在温和无溶剂条件下通过Friedländer缩合反应合成含氮杂环化合物的出色且可持续的催化剂。本文报道的结果表明，与碳材料Norit RX3观察到的催化行为相比，MgO是促进反应最活跃的催化物质。在DFT计算的基础上，提出了一种反应机理，该机理涉及催化剂对反应结构的双重活化。
• Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions
  作者：Amol B. Atar、Someshwer D. Dindulkar、Yeon Tae Jeong

  DOI：10.1007/s00706-012-0906-2

  日期：2013.5

  A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with alpha-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.
• 10.14233/ajchem.2024.31565
  作者：Joshi, Om Prakash、Dash, Ankit Kumar、Thirumoorthi, Ramalingam、Dash, Chandrakanta

  DOI：10.14233/ajchem.2024.31565

  日期：——

  An inexpensive iron-catalyzed annulation of 2-aminobenzaldehydes with iodonium ylides for the synthesis of acridinone derivatives was reported. A library of biologically relevant 3,4-dihydropyridine-1-one scaffold was synthesized by the reaction of corresponding 2-amino benzaldehyde and iodonium ylides under mild reaction conditions in a green solvent. The reaction tolerates various alkyl, aryl and halogenated substrates and affords the desired product in moderate to good yields. The reported reaction has an inexpensive catalytic system, mild reaction conditions, easily accessible substrates and the use of green solvents.
• 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.