2,2,5,5-tetramethyl-9-(3',4'-dihydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 1354390-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2,5,5-tetramethyl-9-(3',4'-dihydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(3,4-dihydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(3,4-dihydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 1354390-09-2
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: XDQGFKQQPKVXHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetramethyl-9-(3',4'-dihydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 0.83h， 以87%的产率得到2,7-dibromo-9-(3,4-dihydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  呫吨二酮的 α-溴化：一种使用 N-溴代琥珀酰亚胺的温和有效的方法

  摘要：

  摘要 目前的工作涉及设计用于在对甲苯磺酸 (PTSA) 存在下使用 N-溴代琥珀酰亚胺 (NBS) 合成 2,7-二溴氧杂蒽二酮的实用有效方案。NBS 和 PTSA 在氯仿中的组合是在温和反应条件下选择性 α-溴化呫吨二酮的有效体系。该方法的主要优点是反应时间短、反应条件温和、易于后处理，此外该方法还具有优异的收率。所有合成的化合物都通过光谱技术进行了表征。

  DOI：

  10.1080/10426507.2021.1987432
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 3,4-二羟基苯甲醛 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 0.5h， 以95%的产率得到2,2,5,5-tetramethyl-9-(3',4'-dihydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  使用离子液体、量子化学研究和抗癌活性合成 1,8-dioxooctahydroxanthene 衍生物

  摘要：

  摘要 使用离子液体 1-丁基-3-甲基咪唑鎓四氟硼酸盐 (BMIF)、1-丁基-3-甲基咪唑鎓溴化物 (BMIB) 和首次开发了无溶剂条件下的 1-丁基-3-甲基咪唑氯化物 (BMIC)。所有合成的化合物 (3a-3k) 都通过光谱数据分析（FT-IR、1H NMR、13C NMR、UV-Vis 和质谱）进行了充分表征。还对合成化合物之一进行了量子化学研究，3,3,6,6-四甲基-9-(2,3,4-三甲氧基苯基)-3,4,5,6,7,9-六氢-1H -呫吨-1,8(2H)-二酮(3a)。分析了所有合成的化合物（3a-3k）对人肺癌细胞系（A549）的体外抗肿瘤活性。在细胞增殖实验中，9-(3,

  DOI：

  10.1016/j.molstruc.2020.127786

文献信息

• Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives
  作者：Selma Zukić、Elma Veljović、Selma Špirtović-Halilović、Samija Muratović、Amar Osmanović、Snežana Trifunović、Irena Novaković、Davorka Završnik

  DOI：10.5562/cca3225

  日期：——

  Ten biologically active 2,2,5,5-tetramethy1-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized and their structures were confirmed by IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Synthesized compounds were scanned for their antioxidant, antimicrobial and antiproliferative activity. Antibacterial activity was tested by the diffusion and dilution method against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, while a ntifunga I activity was tested against Candida albicans and Saccharomyces cerevisiae. Antiproliferative activity was tested against HeLa (cervical carcinoma), SW620 (colorectal adenocarcinoma, metastatic), hepatocellular carcinoma (HEpG2), lung carcinoma cells (A549) and mouse embryo fibroblast cell line (3T3). The best antioxidant activity showed compound 2 with two hydroxy groups substituted on phenyl ring in positions 2' and 3'. The best antimicrobial activity of all synthesized compounds showed compound 8, while the best antiproliferative activity showed compound 6. Results signify the importance of xanthene-1,8-dione derivatives as potential antioxidant and antiproliferative agents.
• XANTHENEDIONE DERIVATIVES FOR THE TREATMENT OF PIGMENTATION AND SKIN AGEING DISORDERS
  申请人：Poigny Stéphane

  公开号：US20130108568A1

  公开（公告）日：2013-05-02

  The invention relates to compound of generic formula (I) in which: R 1 and R 2 represent: OH, a hydrogen atom, a C 1 -C 6 alkyl radical a C 1 -C 6 alkoxy radical, a halogen, or OCOR 3 ; R 3 represents: a C 1 -C 24 alkyl radical a C 12 -C 24 alkenyl radical comprising at least one unsaturation; R 4 represents: COR 5 , a glucide substituted or not by one or more acetyl radical(s); R 5 represents: a C 10 -C 24 alkyl radical or a C 12 -C 24 alkenyl radical comprising at least one unsaturation; R 6 and R 7 represent:—simultaneously a hydrogen atom or a methyl radical, or—when R 6 represents a hydrogen atom, R 7 represents a C 1 -C 6 alkyl radical or a phenyl substituted or not by one or more C 1 -C 3 alkoxy radical(s) or one or more halogen(s) or—R 6 and R 7 are bonded together and form a C 3 -C 6 cycloalkyl, and pharmaceutically or cosmetically acceptable salts.
• US8906416B2
  申请人：——

  公开号：US8906416B2

  公开（公告）日：2014-12-09