7-chloro-9-(2'-chlorophenyl)-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one | 1198210-52-4

• 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-9-(2'-chlorophenyl)-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
• 英文别名: 7-Chloro-9-(2-chlorophenyl)-3,3-dimethyl-2,4-dihydroacridin-1-one
• CAS: 1198210-52-4
• 化学式: C₂₁H₁₇Cl₂NO
• 分子量: 370.278
• InChiKey: SRLLVFHJNHKTRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-9-(2'-chlorophenyl)-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one 在 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 9-chloro-11-(2'-chlorophenyl)-4,4-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-a]acridine
  参考文献：
  名称：

  Efficient Protocol for Synthesis of Pyrazolo[3,4-a]acridines

  摘要：

  A new class of pyrazolo[3,4-a]acridines have been prepared. The synthon acridones were obtained in very good yield by a one-pot reaction of 2-amino-5-chloro or nitro substituted benzophenones with 1,3-cyclic diketones in the presence of freshly prepared Eaton's reagent without solvent, using Friedlander synthesis. The intermediates were reacted with ethylformate followed by hydrazine hydrate to afford pyrazolo[3,4-a]acridines. All of the compounds were purified by recrystallization only, and no chromatographic workup was required. The structures of the synthesized compounds were deduced by spectroscopic techniques, including single-crystal x-ray diffraction.

  DOI：

  10.1080/00397911.2015.1070433
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2-氨基-2-氯苯甲酮 在 benzyltrimethylazanium tetrachloro-λ³-iodanuide 、 溶剂黄146 作用下， 反应 14.0h， 以86%的产率得到7-chloro-9-(2'-chlorophenyl)-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  使用四氯碘酸苄基三甲基铵作为选择性氯化剂和HCl的高效生成剂合成6-氯喹啉

  摘要：

  摘要通过2-氨基芳基酮，α-亚甲基羰基化合物和BTMA ICl 4在AcOH中的三组分反应，可以简单，高效地一锅法合成6-氯喹啉。 图形概要

  DOI：

  10.1007/s00706-009-0170-2

文献信息

• Synthesis of multiple quinoline derivatives using novel ionic liquid-based nano-magnetic catalyst (MNPs@SiO2-Pr-AP-tribromide)
  作者：Arezoo Kharazmi、Ramin Ghorbani-Vaghei、Samira Noori、Sedigheh Alavinia

  DOI：10.1007/s11164-022-04675-z

  日期：2022.4

  increasing attention in the synthesis of the organic compounds. In this study, ionic liquid nano-magnetic pyridinium-tribromide (MNPs@SiO2-Pr-AP-tribromide) as a new nano-catalyst was synthesized. The structure of the catalyst was identified by FT-IR, TGA, XRD, FE-SEM, EDX, EDS, TEM and VSM analysis. The nano-catalyst was efficient for the synthesis of quinoline derivatives through the one-pot reaction

  最近，用各种有机基团功能化的磁性氧化铁纳米颗粒在有机化合物的合成中越来越受到关注。本研究合成了离子液体纳米磁性三溴化吡啶鎓（MNPs@SiO 2 -Pr-AP-三溴化物）作为一种新型纳米催化剂。通过FT-IR、TGA、XRD、FE-SEM、EDX、EDS、TEM和VSM分析对催化剂的结构进行了鉴定。该纳米催化剂通过2-氨基-5-氯二苯甲酮和戊烷-2,4-二酮的一锅反应合成喹啉衍生物是有效的。该催化剂具有制备容易、比表面积大、可再生、热稳定性高、活性高、缩短反应时间、提高效率、易于纯化、反应条件温和等优点。 图形概要 2-氨基芳基酮与羰基化合物之间的反应现在被认为是合成喹啉衍生物的主要策略。在此，我们使用纳米磁性三溴化吡啶鎓 (MNPs@SiO 2 -Pr-AP-三溴化物) 作为制备新型喹啉衍生物的通用催化剂。
• Satheeshkumar; Praveenkumar; Shanmughavel, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 345 - 354
  作者：Satheeshkumar、Praveenkumar、Shanmughavel、Rajendra Prasad

  DOI：——

  日期：——
• Synthesis of 6-chloroquinolines using benzyltrimethylammonium tetrachloroiodate as a selective chlorinating agent and an efficient generator of HCl
  作者：Liqiang Wu、Chunguang Yang、Binxuan Niu、Fulin Yan

  DOI：10.1007/s00706-009-0170-2

  日期：2009.10

  AbstractA simple and efficient one-pot synthesis of 6-chloroquinolines was achieved in good yields via the three-component reaction of 2-aminoaryl ketones, α-methylene carbonyl compounds, and BTMA ICl4 in AcOH. Graphical Abstract

  摘要通过2-氨基芳基酮，α-亚甲基羰基化合物和BTMA ICl 4在AcOH中的三组分反应，可以简单，高效地一锅法合成6-氯喹啉。 图形概要
• Efficient Protocol for Synthesis of Pyrazolo[3,4-<i>a</i>]acridines
  作者：Rajendran Satheeshkumar、Werner Kaminsky、Hazel A. Sparkes、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1080/00397911.2015.1070433

  日期：2015.10.2

  A new class of pyrazolo[3,4-a]acridines have been prepared. The synthon acridones were obtained in very good yield by a one-pot reaction of 2-amino-5-chloro or nitro substituted benzophenones with 1,3-cyclic diketones in the presence of freshly prepared Eaton's reagent without solvent, using Friedlander synthesis. The intermediates were reacted with ethylformate followed by hydrazine hydrate to afford pyrazolo[3,4-a]acridines. All of the compounds were purified by recrystallization only, and no chromatographic workup was required. The structures of the synthesized compounds were deduced by spectroscopic techniques, including single-crystal x-ray diffraction.