9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 331243-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-octahydroxanthene；9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4, 5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 331243-54-0
• 化学式: C₂₅H₃₀O₅
• 分子量: 410.51
• InChiKey: MJEPXLGVNQBDFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  573.8±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 copper(II) oxide 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 3.5h， 生成 9-(3-ethoxy-4-((1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry

  摘要：

  Copper(II) oxide (CuO) nanoparticles have been found to be an efficient catalyst for 1,3-dipolar cycloaddition (CuAAC) of aromatic azides and acetylenic xanthenes furnishing the corresponding xanthene substituted triazoles in excellent yields. CuO nanoparticles have been synthesized from copper acetate by simple co-precipitation method and characterized by scanning electron microscope, energy dispersive X-ray analysis, transmission electron microscope, and X-ray diffraction analysis. The salient features of the present protocol are mild reaction conditions, shorter reaction time, reusability of the catalyst, and applicability to a wide range of substrates. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.016
• 作为产物：
  描述：

  乙基香兰素 、 5,5-二甲基-1,3-环己二酮 在 硼酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.92h， 以86%的产率得到9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  在乙醇-水介质中硼酸催化的呫吨二酮的快速超声合成：两种代表性化合物的单晶、DFT 和 Hirshfeld 表面分析

  摘要：

  摘要 以硼酸为催化剂，在乙醇-水介质中，通过二甲酮与各种芳香醛的缩合，实现了一种高度通用且高效的超声促进合成呫吨二酮衍生物。该方法的优点是反应条件温和、反应时间短、易于后处理、产物可通过非色谱方法纯化，此外该方法还提供了极好的收率。两种呫吨二酮衍生物 3a 和 3b 在重结晶时得到良好的晶体，并且它们的分子结构通过晶体学研究得到证实。晶格中的分子通过弱的分子间 CH•••O 和 CH•••N 相互作用保持在一起。使用 Hirshfeld 表面分析和 DFT/B3LYP 研究进一步深入了解这些相互作用表明，在化合物 3a 中，H•••H (54.7%)，O•••H (18.3%) 和在 3b H•••H (53.7%) 中，O•••H (17.6%) 是稳定晶体结构的分子间相互作用的主要贡献者。为了确定分子电传输特性，我们研究了最高占据、HOMO 和最低未占据、LUMO 轨道之间的能量差异，发现化合物

  DOI：

  10.1016/j.molstruc.2020.129794

文献信息

• [EN] XANTHENEDIONE DERIVATIVES FOR THE TREATMENT OF PIGMENTATION AND SKIN AGEING DISORDERS<br/>[FR] DÉRIVÉS DE XANTHÈNEDIONE POUR LE TRAITEMENT DE TROUBLES DE PIGMENTATION ET DE VIEILLISSEMENT DE LA PEAU
  申请人：FABRE PIERRE DERMO COSMETIQUE

  公开号：WO2012004390A1

  公开（公告）日：2012-01-12

  The invention relates to compound of generic formula (I) in which: R1 and R2 represent: OH, a hydrogen atom, a C1-C6 alkyl radical a C1-C6 alkoxy radical, a halogen, or OCOR3; R3 represents: a C1-C24 alkyl radical a C12-C24 alkenyl radical comprising at least one unsaturation; R4 represents: COR5, a glucide substituted or not by one or more acetyl radical(s); R5 represents: a C10-C24 alkyl radical or a C12-C24 alkenyl radical comprising at least one unsaturation; R6 and R7 represent: - simultaneously a hydrogen atom or a methyl radical, or - when R6 represents a hydrogen atom, R7 represents a C1-C6 alkyl radical or a phenyl substituted or not by one or more C1-C3 alkoxy radical(s) or one or more halogen(s) or - R6 and R7 are bonded together and form a C3-C6 cycloalkyl, and pharmaceutically or cosmetically acceptable salts.

  该发明涉及通式(I)的化合物，其中：R1和R2代表：OH，氢原子，C1-C6烷基基团，C1-C6烷氧基团，卤素，或OCOR3；R3代表：C1-C24烷基基团，至少含有一种不饱和的C12-C24烯基基团；R4代表：COR5，一种被一个或多个乙酰基取代或未取代的糖苷；R5代表：C10-C24烷基基团或至少含有一种不饱和的C12-C24烯基基团；R6和R7代表：-同时是氢原子或甲基基团，或-当R6代表氢原子时，R7代表C1-C6烷基基团或一个被一个或多个C1-C3烷氧基或一个或多个卤素取代或未取代的苯基；或-R6和R7结合在一起形成一个C3-C6环烷基，并且是药用或化妆品中可接受的盐。
• Evaluation of xanthene-appended quinoline hybrids as potential leads against antimalarial drug targets
  作者：R. Jesu Jaya Sudan、J. Lesitha Jeeva Kumari、P. Iniyavan、S. Sarveswari、V. Vijayakumar

  DOI：10.1007/s11030-022-10450-4

  日期：——

  performed to find the binding efficacy of all these newly synthesized compounds towards thirteen antimalarial drug targets. Molecular dynamics simulation was carried out to predict the stability of the ligand-bound complex in a solvent medium. Blind and site-directed docking with compounds 6a–n against 13 drug targets revealed most of the ligands to have a good binding affinity with the targets. Analysis

  摘要 一系列稠合杂环呫吨附加喹啉 6a–n 成功合成，具有区域选择性，并使用 IR、1 H NMR、13进行表征C NMR 和质谱数据。进行分子对接以发现所有这些新合成的化合物对十三个抗疟药靶标的结合功效。进行分子动力学模拟以预测配体结合复合物在溶剂介质中的稳定性。化合物 6a–n 与 13 个药物靶标的盲法和定点对接表明，大多数配体与靶标具有良好的结合亲和力。基于结合能、配体的结合方式、分子间相互作用和药效团的分析，我们仅鉴定了一种配体-受体复合物以提供更好的结果。所选受体-配体复合物的分子动力学模拟表明，合成化合物与受体的结合亲和力优于天然配体复合物。 图形概要
• A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound
  作者：Naveen Mulakayala、G. Pavan Kumar、D. Rambabu、Madhu Aeluri、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2012.10.024

  日期：2012.12

  The ceric ammonium nitrate (CAN) has been identified as an efficient and eco-friendly catalyst for the one pot and virtually three-component reaction of 5,5-dimethyl-1,3-cyclohexanedione with various aldehydes in 2-propanol. Under ultrasound irradiation, the reaction proceeded smoothly at a faster rate at 50 degrees C affording a variety of 9-alkyl/aryl/heteroaryl substituted 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good to excellent yields. A probable mechanism for this CAN-mediated synthesis of 1,8-dioxo-octahydroxanthene derivatives is presented. Overall, the methodology provides advantages such as low cost, high yields of products and simple operational procedures and is free from the use of harmful chlorinated solvents. (C) 2012 Elsevier Ltd. All rights reserved.
• Green approach for the synthesis of xanthenedione derivatives: crystal structure, DFT, and Hirshfeld surface analysis
  作者：R. Shashi、Noor Shahina Begum、Anoop Kumar Panday、Sabine Foro

  DOI：10.1080/15421406.2021.1946350

  日期：2021.11.22
• 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.