9-(4-hydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 9-(4-hydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-hydroxyphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: CAJIXRCHRHEPNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(4-hydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 、 邻甲基氯化苄 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以58%的产率得到9-(4-((2-methylbenzyl)oxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  用于 δ-阿片受体的新型 9-芳基呫吨二酮基变构调节剂的设计、合成和评价

  摘要：

  慢性疼痛和抑郁都是广泛流行的合并症。虽然有效，但基于 μ-阿片受体的药物与危及生命的副作用有关，包括呼吸抑制、依赖和成瘾。与μ-阿片受体相比，δ-阿片受体是一种很有前途的慢性疼痛和抑郁症的替代生物靶标，因为它的靶向副作用显着降低。先前的一项研究确定了两种 δ-阿片受体阳性变构调节剂。在此，我们报告了针对最初描述的 SAR 以前未探索区域的五系列化合物的设计。评估了类似物增强 Leu-脑啡肽激动剂反应的能力。在 30 个类似物中，化合物6g与 cAMP 抑制相比，显示出增强 ERK1/2 磷酸化信号的趋势，而化合物11c显示出将信号偏向转向 cAMP 抑制的趋势。6g和11c都作为有前途的工具化合物出现，可用于设计需要特定下游信号属性的前瞻性疗法。

  DOI：

  10.1021/acs.jmedchem.2c01061
• 作为产物：
  描述：

  1,3-环己二酮 、 对羟基苯甲醛 以 甘油 为溶剂， 反应 6.0h， 以92%的产率得到9-(4-hydroxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/b916015a

文献信息

• A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions
  作者：Behrooz Maleki、Shahram Barzegar、Zeinalabedin Sepehr、Mina Kermanian、Reza Tayebee

  DOI：10.1007/s13738-012-0092-5

  日期：2012.10

  simple, efficient, and environmentally benign route was developed for the preparation of 14-aryl or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxo-octahydroxanthene and 12-aryl—8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones from condensation of various aldehydes with (i) β-naphthol, (ii) cyclic 1,3-dicarbonyl compounds and (iii) β-naphthol and cyclic 1,3-dicarbonyl compounds, using novel polymeric catalyst [poly(AMPS-co-AA)]

  开发了一种简单，有效且环境友好的方法，用于制备14-芳基或烷基14 H-二苯并[a，j]氧杂蒽，1,8-二氧代-八氢氧杂蒽和12-芳基-8,9,10，各种醛与（i）β-萘酚，（ii）环状1,3-二羰基化合物和（iii）β-萘酚和环状1,3-二羰基化合物缩合而成的12-四氢苯并[a]黄嘌呤-11-酮，在无溶剂条件下使用新型聚合物催化剂[聚（AMPS-co-AA）]。使用容易获得的催化剂，更短的反应时间，更好的产率，反应的简单性，非均相系统和容易的后处理是本方法的优点。
• Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives
  作者：Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi、Mohadeseh Seddighi、Omid Goli Jolodar

  DOI：10.1007/s11164-014-1905-1

  日期：2015.11

  1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.

  1,8-二氧杂-八氢化咕吨类化合物可通过醛与1,3-环己二酮和/或双甲酮在新型高效的N-磺化DABCO催化剂作用下缩合反应制得。该试剂同样能高效催化醛与巴比妥酸的缩合反应，生成5-芳亚甲基-嘧啶-2,4,6-三酮。产物结构通过其红外光谱、核磁共振氢谱和碳谱得以表征。本方法具有多种优势，如催化剂制备与处理简便、产率高、操作简单且环保、成本低、反应时间短、后处理简便，以及可在无溶剂条件下或使用水作为绿色溶剂的情况下预先进行反应。
• Magnetic Fe–Cr–Ni oxide alloy nano-belts prepared from the chemical decomposition of a stainless steel screw (a top-down approach): an efficient and cheap catalyst for multicomponent reactions
  作者：Milad Kazemnejadi、Zeinab Sharafi、Boshra Mahmoudi、Atefeh Zeinali、Mohammad Ali Nasseri

  DOI：10.1007/s13738-019-01814-z

  日期：2020.4

  A new, cheap, and accessible method has been used for the preparation of nano-belts from the chemical decomposition (top-down approach) of a cheap stainless steel screw and found as an efficient magnetically recyclable nanocatalyst for the preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild reaction conditions. The nano-belts, Fe–Cr–Ni oxide alloy, was prepared in a two-step synthesis and characterized with various instrumental methods. Due to magnetic property of the screw (a ferritic-alloy), the resultant nano-belts is magnetic. Magnetic Fe–Cr–Ni alloy nano-belts were applied toward efficient preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild conditions. The catalyst could be readily recovered and recycled for several consecutive runs, while it suffers from a very low metal leaching and subsequently efficiency drop.

  一种新的、廉价且易得的方法已被用于从廉价不锈钢螺丝的化学分解（自上而下的方法）中制备纳米带，并发现其在温和反应条件下作为高效的磁性可回收纳米催化剂，用于喹啉和1,8-二氧杂-八氢氧杂蒽的制备。这种纳米带，即Fe–Cr–Ni氧化物合金，是通过两步合成法制备的，并使用多种仪器方法进行了表征。由于螺丝（一种铁素体合金）的磁性特性，所得纳米带也具有磁性。磁性Fe–Cr–Ni合金纳米带在温和条件下被应用于高效制备喹啉和1,8-二氧杂-八氢氧杂蒽。该催化剂可以轻易地回收并在多次连续运行中循环使用，同时金属溶出现象极少，因此催化效率几乎不会下降。
• 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。
• An efficient route to 1,8-dioxo-octahydroxanthenes and -decahydroacridines using a sulfated zirconia catalyst
  作者：Sandeep S. Kahandal、Anand S. Burange、Sandip R. Kale、Pepijn Prinsen、Rafael Luque、Radha V. Jayaram

  DOI：10.1016/j.catcom.2017.03.017

  日期：2017.7

  Sulfated zirconia results to be a very efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines without tedious work-up procedures. While 1,8-dioxo-octahydroxanthenes are prepared from aldehyde and 5,5-dimethyl-1,3-cyclohexenedione (dimedone), 1,8-dioxo-decahydroacridines are prepared from this reactant mixture with amines. This method provides a mild catalytic

  硫酸化的氧化锆是一种非常有效的催化剂，用于合成1,8-二氧-八氢黄嘌呤和1,8-二氧-十氢ac啶，无需进行繁琐的后处理程序。尽管由醛和5,5-二甲基-1,3-环己二酮（二甲酮）制备1,8-二氧-八氢黄嘌呤，而由该反应物与胺的混合物制备1,8-二氧-十氢ac啶。该方法为合成功能化的x吨和a啶衍生物提供了温和的催化方案。通过XRD，FT-IR，TGA-DSC，SEM-EDAX和表面酸度对催化剂进行了表征，并显示了高达6个连续循环的优异可重复使用性。