2,5-Dichlor-3,6-dimorpholin-p-benzochinon | 73713-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-Dichlor-3,6-dimorpholin-p-benzochinon
• 英文别名: 2,5-dichloro-3,6-di-morpholin-4-yl-[1,4]benzoquinone；2,5-dichloro-3,6-dimorpholino-[1,4]benzoquinone；2,5-Dichlor-3,6-dimorpholino-[1,4]benzochinon；2,5-Dichlor-3,6-dimorpholino-benzochinon-(1,4)；2,5-Dichlor-3,6-dimorpholino-benzo-1,4-chinon；p-Benzoquinone, 2,5-dichloro-3,6-dimorpholino-；2,5-dichloro-3,6-dimorpholin-4-ylcyclohexa-2,5-diene-1,4-dione
• CAS: 73713-78-7
• 化学式: C₁₄H₁₆Cl₂N₂O₄
• 分子量: 347.198
• InChiKey: BEUXSCOHTNUOOS-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  455.0±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-Dichlor-3,6-dimorpholin-p-benzochinon 生成 1,4-diacetoxy-2,5-dichloro-3,6-dimorpholino-benzene
  参考文献：
  名称：

  Henry; Smith, Journal of the American Chemical Society, 1952, vol. 74, p. 278

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉 、 四氯苯醌 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.42h， 以71.18%的产率得到2,5-Dichlor-3,6-dimorpholin-p-benzochinon
  参考文献：
  名称：

  Strukturen ladungsgestörter oder räumlich überfüllter Moleküle, 80 [1 - 3] Strukturänderungen von p-Benzochinon durch Donator- und Akzeptor-Substituenten

  摘要：

  本文介绍并讨论了七种二取代或四取代的对苯醌衍生物O=C(XC=CH)₂C=O和O=C(XC=CX)₂C=O的结构，其中取代基X = -OCH₃，-N(CH₂)₅，-N(CH₂CH₂)₂O，-Cl，-CN和-⊕N(HC=CH)₂C-N(CH₃)₂，并与已发表的取代基为X = -Si(CH₃)₃，-C₆H₅，-N(CH₃)₂，-⊕N(HC=CH)₂CN(CH₃)₂，-O⊖和-NO₂的结构进行比较。根据介绍，利用半波还原电位、几何优化的量子化学计算对取代基扰动以及已知的对苯醌衍生物的结构数据来表征它们的分子基态。结构变化表明了取代基扰动可能如何被合理解释。在定义的类别中 - 未受扰动、给体、给体/受体和受体扰动中 - 给体取代的对苯醌通常表现出最大的差异，通常被称为靛蓝畸变。与广泛的半经验计算非常一致，实验确定的所有效应都根据不同的电荷分布进行讨论。关于对生物化学重要性的对苯醌衍生物，这个首次的结构摘要指出了重要的方面。

  DOI：

  10.1515/znb-1996-0201

文献信息

• Small molecule ferroptosis inducers
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US10947188B2

  公开（公告）日：2021-03-16

  The present invention provides, inter alia, a compound according to formula (I): Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for regulating GPX4 in a cell and methods for inducing ferroptosis in a cell.

  本发明特别提供了一种符合式 (I) 的化合物： 还提供了含有药学上可接受的载体和根据本发明的化合物的组合物。此外，还提供了调节细胞中 GPX4 的方法和诱导细胞中铁细胞凋亡的方法。
• Buckley et al., Journal of the Chemical Society, 1957, p. 4880,4889
  作者：Buckley et al.

  DOI：——

  日期：——
• Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifungal agents
  作者：Vishnu K. Tandon、Sandeep Kumar、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2012.07.022

  日期：2012.10

  Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio) cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929. (C) 2012 Elsevier Masson SAS. All rights reserved.
• New type of quinone-quinone complexation in the reaction of 2,5-dichloro-1,4-benzoquinone with morpholine at high pressure
  作者：S. V. Chapyshev、T. Ibata

  DOI：10.1007/bf01433999

  日期：1996.2

  The complex of tetrakis(morpholino)-1,4-benzoquinone with 2,5-bis(morpholino)-1,4-benzoquinone of 2:1 stoichiometry was obtained in 9% yield in the reaction of 2,5-dichloro-1,4-benzoquinone with morpholine at high pressure.
• SMALL MOLECULE FERROPTOSIS INDUCERS
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20190315681A1

  公开（公告）日：2019-10-17

  The present invention provides, inter alia, a compound according to formula (I): Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for regulating GPX4 in a cell and methods for inducing ferroptosis in a cell.