3-chloro-4-(4-methoxyphenyl)-3-cyclobutene-1,2-dione | 69009-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-4-(4-methoxyphenyl)-3-cyclobutene-1,2-dione
• 英文别名: 3-chloro-4-(4-methoxyphenyl)cyclobut-3-ene-1,2-dione
• CAS: 69009-33-2
• 化学式: C₁₁H₇ClO₃
• 分子量: 222.628
• InChiKey: XFTUGNYHMOMVDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(4-methoxyphenyl)-3-cyclobutene-1,2-dione 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 3-环丁烯-1,2-二酮,3-羟基-4-(4-甲氧苯基)-
  参考文献：
  名称：

  Squaric Acids:  A New Motif for Designing Inhibitors of Protein Tyrosine Phosphatases

  摘要：

  Protein tyrosine phosphatases (PTPases) are important targets in medicinal chemistry. These enzymes play a role in a number of human diseases, including type 11 diabetes and infection by Yersinia pestis, the causative agent of bubonic plague. Derivatives of squaric acids such as 2-aryl-1-hydroxycyclobut-1-ene-3,4-diones represent a new class of monoanionic inhibitors for PTPases.

  DOI：

  10.1021/ol036121w
• 作为产物：
  描述：

  4-甲氧基苯乙酰氯 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 生成 3-chloro-4-(4-methoxyphenyl)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Synthesis and reactivity of compounds with cyclobutane ring(s). 11. [2 + 2] Cycloadditions of tetraalkoxyethylenes with ketenes: a general route to 2-substituted 1-hydroxycyclobut-1-ene-3,4-diones

  摘要：

  DOI：

  10.1021/ja00493a052

文献信息

• Synthesis of the Substituted 3‐Cyclobutene‐1,2‐diones
  作者：Sergey A. Ivanovsky、Mikhail V. Dorogov、Dmitry V. Kravchenko、Alexandre V. Ivachtchenko

  DOI：10.1080/00397910701462716

  日期：2007.8

  reported. Unsymmetrically substituted 3,4‐diamino‐3‐cyclobutene‐1,2‐diones and 3‐amino‐4‐hydroxy‐3‐cyclobutene‐1,2‐diones were prepared by interaction of diethyl squarate with different nucleophilic reagents such as alkali, primary and secondary amines and amino acids. Substituted 3‐amino‐4‐aryl‐3‐cyclobutene‐1,2‐diones were synthesized by interaction of squaryl dichloride with different arenes followed

  摘要 报道了一种新型方酸衍生物的简便合成方法。不对称取代的 3,4-二氨基-3-环丁烯-1,2-二酮和 3-氨基-4-羟基-3-环丁烯-1,2-二酮是通过方酸二乙酯与不同的亲核试剂（如碱、伯胺和仲胺和氨基酸。取代的 3-氨基-4-芳基-3-环丁烯-1,2-二酮是通过二氯化方酸芳基与不同芳烃的相互作用以及胺的芳基方酸化作用合成的。开发了有效的程序来随后取代方酸二乙酯中的乙氧基和二氯化方芳基中的氯原子。合成的化合物具有很大的生物活性潜力，是生物医学筛选的有用对象。
• Synthesis and antitumor activity of novel 3,4-diaryl squaric acid analogs
  作者：Zong-ying Liu、Yue-ming Wang、Yan-xing Han、Ling Liu、Jie Jin、Hong Yi、Zhuo-rong Li、Jian-dong Jiang、David W. Boykin

  DOI：10.1016/j.ejmech.2013.04.046

  日期：2013.7

  A series of novel 3,4-diaryl squaric acid analogs 4a-r related to combretastatin A-4 (CA4) using squaric acid as the cis-restricted linker were prepared and studied for their anticancer activity against selected human cancer cell lines. New compounds 4g, 4k, 4m, 4n, 4p, 4q and 4r exhibit strong activities against human leukemia cells with IC50 values of <= 20 nM and compounds 4k, 4n, 4p, 4q and 4r showed potent activities against a panel of human tumor cell lines. Compounds 4n and 4p arrest tumor cell cycle in G2-M phase. Computational modeling analysis suggests that the binding mechanism of compound 4n to the colchicine binding site on the microtubules is similar to that of CA4. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Selective 1,4-Addition of Arenes to 3-Chloro-3-cyclobutene-1,2-dione under Friedel−Crafts Conditions. Synthesis and Reactivity of 4-Aryl-3-chloro-2-hydroxy-2-cyclobuten-1-ones¹
  作者：Arthur H. Schmidt、Gunnar Kircher、Stephan Maus、Heinz Bach

  DOI：10.1021/jo952062r

  日期：1996.1.1

  The reaction of semisquaric chloride (7) with arenes 2 has been investigated. In the presence of 1.1 equiv of AlCl3 and in the temperature range of -15 degrees C to rt the arenes 2a-q afford the 4-aryl-3-chloro-2-hydroxy-2-cyclobuten-1-ones (chloroenols) 8a-q in good yield. By contrast, 7 reacts with 1,4-dimethoxybenzene (21) in boiling CH2Cl2 to give a mixture of (2,5-dimethoxyphenyl)cyclobutenedione (9a) (27% yield) and bis(2,5-dimethoxyphenyl)cyclobutenedione (10a) (8% yield). With 1,2,4-trimethoxybenzene (2r) in the presence of trifluoroacetic acid is generated (2,4,5-trimethoxyphenyl)cyclobutenedione (9b) in 21% yield. The chloroenols 8 allow a series of valuable transformation reactions: with diazomethane the chloroenol methyl ethers 11 are generated, with chlorine the 3-aryl-4-chlorocyclobutenediones 12, and with bromine in MeOH the 3-aryl-4-methoxycyclobutenediones 13. In DMSO or in acetone/H2O the chloroenols 8 eliminate HCl, furnishing the arylcyclobutenediones 14. In a mixture of acetone -d(6)/D2O/DCl are obtained 4-aryl-cyclobutenediones-3-d 15. For the latter two processes the corresponding 3-aryl-4-chlorocyclobutane-1,2-diones 16 are postulated as intermediates. Thermolysis of the chloroenols 8 and the chloroenol methyl ethers 11 in refluxing m-xylene afforded the 3-chloro-1,2-dihydroxynaphthalenes 17 and the 3-chlorol-hydroxy-2-methoxynaphthalenes 18, respectively.
• Selective Cross-Couplings. Sequential Stille−Liebeskind/Srogl Reactions of 3-Chloro-4-arylthiocyclobutene-1,2-dione
  作者：Angélica Aguilar-Aguilar、Eduardo Peña-Cabrera

  DOI：10.1021/ol701628z

  日期：2007.10.1

  The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogi reaction conditions (in the presence of a Cu(l) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).
• Expanding the squaramide library as mycobacterial ATP synthase inhibitors: Innovative synthetic pathway and biological evaluation
  作者：Jan Chasák、Lauren Oorts、Milan Dak、Veronika Šlachtová、Václav Bazgier、Karel Berka、Linda De Vooght、Natalia Smiejkowska、Kevin Van Calster、Laurence Van Moll、Davie Cappoen、Paul Cos、Lucie Brulíková

  DOI：10.1016/j.bmc.2023.117504

  日期：2023.11