9-(4-hydroxy-3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 102159-41-1

• 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-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-hydroxy-3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 102159-41-1
• 化学式: C₂₀H₂₀O₅
• mdl: MFCD00593297
• 分子量: 340.376
• InChiKey: UMPROAWIQHDPNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  5-苯基异噁唑-3-羰酰氯 、 9-(4-hydroxy-3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 三乙胺 作用下， 以 乙醚 为溶剂， 以81%的产率得到4-(1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-2-methoxyphenyl-5-phenylisoxazole-3-carboxylate
  参考文献：
  名称：

  Catalytic Synthesis of 1,2-Azole and Pyridine Derivatives of 1,8-Dioxooctahydroxanthenes Using FIBAN K-1 Fibrous Sulfonic Cation Exchanger

  摘要：

  DOI：

  10.1134/s1070363223030027
• 作为产物：
  描述：

  2,2'-((4-hydroxy-3-methoxyphenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one) 在 FIBAN K-1 作用下， 以 苯 为溶剂， 以84%的产率得到9-(4-hydroxy-3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  Catalytic Synthesis of 1,2-Azole and Pyridine Derivatives of 1,8-Dioxooctahydroxanthenes Using FIBAN K-1 Fibrous Sulfonic Cation Exchanger

  摘要：

  DOI：

  10.1134/s1070363223030027

文献信息

• A Green and Efficient Synthesis of 9-Aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using a Task-Specific Ionic Liquid as Dual Catalyst and Solvent
  作者：Jingjun Ma、Xin Zhou、Xiaohuan Zang、Chun Wang、Zhi Wang、Jingci Li、Qing Li

  DOI：10.1071/ch06225

  日期：——

  A green and efficient method for the preparation of 9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione has been developed using functionalized ionic liquids as a catalyst and a reaction medium. The nature of both the counter anion and cation influence the catalytic performance of the ionic liquids. The ionic liquid can be recycled and reused without apparently loss of activity.

  以功能化离子液体为催化剂和反应介质，开发了一种制备 9-芳基-3,4,5,6,7,9-六氢-1H-呫吨-1,8(2H)-二酮的绿色高效方法。阴阳离子的性质会影响离子液体的催化性能。离子液体可以回收和重复使用，而不会明显丧失活性。
• Envirocat EPZ-10: A Solid Acid Catalyst for the Synthesis of 1,8-Dioxo-octahydroxanthenes in Aqueous Medium
  作者：D. M. Pore、T. S. Shaikh、N. G. Patil、S. B. Dongare、U. V. Desai

  DOI：10.1080/00397910903221027

  日期：2010.7.12

  An efficient method for synthesis of 1,8-dioxo-octahydroxanthenes using EPZ-10 as a heterogeneous catalyst is developed. In this method, aldehydes and dimedone / cyclohexane-1,3-dione are heated at 70 °C in the presence of a catalytic amount of EPZ-10 in water as a universal solvent, affording the corresponding 1,8-dioxo-octahydroxanthenes in moderate to excellent yields. Also, domino Knoevenagel /

  开发了一种使用 EPZ-10 作为非均相催化剂合成 1,8-二氧代-八氢氧杂蒽的有效方法。在该方法中，醛和二甲酮/环己烷-1,3-二酮在作为通用溶剂的水中催化量的 EPZ-10 存在下在 70 °C 下加热，得到相应的 1,8-二氧代-八氢氧杂蒽中等至极好的产量。此外，在没有任何催化剂的情况下，多米诺骨牌 Knoevenagel / 杂迈克尔加成反应被描述为具有优异的产率。该方法的主要优点是收率高、反应时间短、操作简便。这种绿色方案适用于二甲酮和环己烷-1,3-二酮。
• Glycerol as a promoting medium for electrophilic activation of aldehydes: catalyst-free synthesis of di(indolyl)methanes, xanthene-1,8(2H)-diones and 1-oxo-hexahydroxanthenes
  作者：Fei He、Peng Li、Yanlong Gu、Guangxing Li

  DOI：10.1039/b916015a

  日期：——

  Glycerol was used, for the first time, as a green and effective promoting medium for electrophilic activation of aldehydes, and with which, a catalyst-free system for some reactions that conventionally carried out using acid catalysts, such as synthesis of di(indolyl)methanes, 3,4,5,6,7,9-hexahydro-9-aryl-1H-xanthene-1,8(2H)-dione and 1-oxo-hexahydroxanthenes, was developed.

  甘油首次被用作绿色有效的促进介质，用于醛的电亲和活化，并基于此开发了一种无催化剂的体系，用于一些传统上使用酸催化剂进行的反应，例如二(吲哚基)甲烷、3,4,5,6,7,9-六氢-9-芳基-1H-黄酮-1,8(2H)-二酮和1-氧基-六氢黄酮的合成。
• CsF mediated rapid condensation of 1,3-cyclohexadione with aromatic aldehydes: Comparative study of conventional heating vs. ambient temperature
  作者：Kamalakar P. Nandre、Vijay S. Patil、Sidhanath V. Bhosale

  DOI：10.1016/j.cclet.2011.01.002

  日期：2011.7

  A mild, efficient and high yielding protocol for the synthesis of 2,2′-arylmethelene dicyclohexane-1,3-dione derivatives at room temperature and 9-aryl-1,8-dihydrooctahydroxanthene at conventional heating using cesium fluoride as a catalyst is reported. The major advantages of this reaction are excellent yield, very short reaction time and use of inexpensive catalyst.

  据报道，使用氟化铯作为催化剂，在常规加热条件下，室温下合成2,2'-芳基亚甲基二环己烷-1,3-二酮衍生物和9-芳基-1,8-二氢八氢oct吨蒽的合成反应温和，高效，高收率。 。该反应的主要优点是优异的产率，非常短的反应时间和使用廉价的催化剂。
• [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。