9-(4-hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 37797-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 9-(4-hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 37797-16-3
• 化学式: C₂₅H₃₀O₆
• mdl: MFCD00809837
• 分子量: 426.51
• InChiKey: PYHWTCDGAJHFQK-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C(Solv: ethanol (64-17-5))
• 沸点：
  584.6±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 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：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(4-hydroxy-3,5-dimethoxyphenyl)-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-(3,5-dimethoxy-4-((1-phenyl-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：

  5,5-二甲基-1,3-环己二酮 、 丁香醛 以 乙醇 为溶剂， 以91 %的产率得到9-(4-hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  樟脑磺酸催化一锅假三组分合成一系列1,8-二氧代八氢呫吨及其五种衍生物的比较晶体结构研究和赫什菲尔德表面分析

  摘要：

  开发了一种简单方便的方案，用于在催化量的樟脑磺酸存在下，通过两当量双甲酮和一当量芳香醛之间的一锅假三组分反应合成1,8-二氧代八氢呫吨。在回流条件下，酸作为乙醇中的有效有机催化剂。使用了多种芳基醛和杂芳基醛，所有这些都提供了所需产物的优异产率。通过简单的结晶技术以优异的产率分离出纯的合成产物。有机催化剂的使用、简单的后处理程序、高原子经济性、多组分策略、简单的分离程序和优异的产率是这个新开发的方案的一些主要优点。五个这样合成的X射线晶体学数据1，还记录了 8-二氧代-八氢呫吨衍生物。还进一步分析了这五种 1,8-二氧代-八氢呫吨衍生物的 3D Hirshfeld 表面和联合 2D 指纹图，以了解分子相互作用。 图形概要

  DOI：

  10.1007/s11164-023-05064-w

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。
• Synthesis and antioxidant studies of novel bi-, tri-, and tetrapodal 9-aryl-1,8-dioxo-octahydroxanthenes
  作者：P. Iniyavan、S. Sarveswari、V. Vijayakumar

  DOI：10.1016/j.tetlet.2015.01.162

  日期：2015.3

  Compounds bearing two, three, and four 9-aryl-1,8-dioxo-octahydroxanthenes units were synthesized by regioselective O-alkylation of monopodal xanthenes with bis-, tris-, and tetralds(bromomethyl)benzenes as alkylating agents using K2CO3 as base and DMF as solvent in moderate temperature. All the synthesized compounds were characterized by NMR and mass spectral data and then tested for antioxidant activity, as reflected by free radical scavenging, increased with increasing number of xanthene units. (C) 2015 Elsevier Ltd. All rights reserved.
• XANTHENEDIONE DERIVATIVES FOR THE TREATMENT OF PIGMENTATION AND SKIN AGEING DISORDERS
  申请人：Pierre Fabre Dermo-Cosmétique

  公开号：EP2590959A1

  公开（公告）日：2013-05-15
• US8906416B2
  申请人：——

  公开号：US8906416B2

  公开（公告）日：2014-12-09
• CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry
  作者：P. Iniyavan、G.L. Balaji、S. Sarveswari、V. Vijayakumar

  DOI：10.1016/j.tetlet.2015.07.016

  日期：2015.8

  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.