ethyl 1,9-dioxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate | 188015-75-0

• 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: ethyl 1,9-dioxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate
• 英文别名: Ethyl 1,9-dioxo-2,3,4,10-tetrahydroacridine-4-carboxylate
• CAS: 188015-75-0
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: IFBLXUOXUVLUBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1,9-dioxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 ethyl 1-hydrazono-9-oxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate
  参考文献：
  名称：

  吡唑并[3,4,5- kl ] ac啶和吲哚并[2,3- a ] ac啶的潜在抗癌衍生物的合成及细胞毒性

  摘要：

  通过1,9-二氧-1,2,3,4,9,10-六氢hydro啶-4-羧酸乙酯（4）与肼及其甲基和2的反应制备吡唑并[3,4,5- kl ] ac啶-（二甲基氨基）乙基衍生物，然后用1，4-苯醌将中间产物芳构化。还进行酯官能到羧酰胺的转化，并且N-（2-（二甲基氨基）乙基）-1-（2-（二甲基氨基）乙基）-1，2-二氢吡唑并[3,4,5- KL ] ac啶-5-羧酰胺（13c）在一组细胞系中具有明显的细胞毒性。4与4-甲氧基苯基肼反应生成新的吲哚[2，3- a ] ac啶衍生物。

  DOI：

  10.1016/s0040-4020(01)01119-x
• 作为产物：
  描述：

  2-(4-Oxo-1,4-dihydro-quinolin-2-yl)-pentanedioic acid diethyl ester 在 PPA 作用下， 反应 16.0h， 以78%的产率得到ethyl 1,9-dioxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate
  参考文献：
  名称：

  A Versatile Synthesis of Acridine-1,9-Diones

  摘要：

  Alkylation of ethyl 2-(4-oxo-1,4-dihydroquinolin-2-yl)acetate by Michael addition with various alkenes has been carried out. The C-alpha alkylated intermediates so formed can be cyclized with hot polyphosphoric acid to acridine-1,9-diones.

  DOI：

  10.1080/00397919708004810

文献信息

• Synthesis of some acridone alkaloids and related compounds
  作者：Jun-Jie Chen、Leslie W Deady、Maureen F Mackay

  DOI：10.1016/s0040-4020(97)00792-8

  日期：1997.9

  An efficient Pd/C aromatization of 1,2,3,4,9,10-hexahydroacridine-1,9-diones to 1-hydroxyacridones is reported. The previously reported four-step synthesis of the diones has been extended to give a number of methoxy substituted derivatives and the aromatization reaction, along with hydrobromic acid demethylation, provides a useful route to various methoxy and hydroxy substituted acridones.

  报道了将1,2,3,4,9,10-六氢ac啶-1,9-二酮有效的Pd / C芳构化为1-羟基ac啶酮。先前报道的二酮的四步合成已扩展为提供许多甲氧基取代的衍生物，并且芳构化反应以及氢溴酸脱甲基化提供了通往各种甲氧基和羟基取代的cri啶的有用途径。
• Synthesis and cytotoxicity of potential anticancer derivatives of pyrazolo[3,4,5-kl]acridine and indolo[2,3-a]acridine
  作者：Xianyong Bu、Junjie Chen、Leslie W Deady、William A Denny

  DOI：10.1016/s0040-4020(01)01119-x

  日期：2002.1

  5-kl]acridines were prepared by reaction of ethyl 1,9-dioxo-1,2,3,4,9,10-hexahydroacridine-4-carboxylate (4) with hydrazine and its methyl and 2-(dimethylamino)ethyl derivatives, followed by aromatization of the intermediate products with 1,4-benzoquinone. Conversion of the ester function to a carboxamide was also carried out and N-(2-(dimethylamino)ethyl)-1-(2-(dimethylamino)ethyl)-1,2-dihydropyrazolo[3

  通过1,9-二氧-1,2,3,4,9,10-六氢hydro啶-4-羧酸乙酯（4）与肼及其甲基和2的反应制备吡唑并[3,4,5- kl ] ac啶-（二甲基氨基）乙基衍生物，然后用1，4-苯醌将中间产物芳构化。还进行酯官能到羧酰胺的转化，并且N-（2-（二甲基氨基）乙基）-1-（2-（二甲基氨基）乙基）-1，2-二氢吡唑并[3,4,5- KL ] ac啶-5-羧酰胺（13c）在一组细胞系中具有明显的细胞毒性。4与4-甲氧基苯基肼反应生成新的吲哚[2，3- a ] ac啶衍生物。
• A Versatile Synthesis of Acridine-1,9-Diones
  作者：Junjie Chen、Leslie W. Deady

  DOI：10.1080/00397919708004810

  日期：1997.1.1

  Alkylation of ethyl 2-(4-oxo-1,4-dihydroquinolin-2-yl)acetate by Michael addition with various alkenes has been carried out. The C-alpha alkylated intermediates so formed can be cyclized with hot polyphosphoric acid to acridine-1,9-diones.