9-(2-chlorophenyl)-1,8-dioxo-octahydroxanthene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9-(2-chlorophenyl)-1,8-dioxo-octahydroxanthene
• 英文别名: 9-(2-chlorophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(2-chlorophenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• 化学式: C₁₉H₁₇ClO₃
• 分子量: 328.795
• InChiKey: GVRCQFIBAUAZLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[(2-Chlorophenyl)-(2,6-dioxocyclohexyl)methyl]cyclohexane-1,3-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 9-(2-chlorophenyl)-1,8-dioxo-octahydroxanthene
  参考文献：
  名称：

  摘要：

  Several 9-(2-R phenyl)xanthenediones have been synthesized and the x-ray diffraction structure for the 2-methylphenyl derivative (4b) has been determined. This compound crystallizes in the monoclinic system, space group P2(1)/n, with a = 11.729 (3), b = 9.674 (3), c = 14.628 (4) Angstrom, and beta = 106.30 degrees. It presents a partially hydrogenated xanthene system in distorted boat conformation for the heterocyclic central ring, and an almost ideal envelope conformation for the outer rings. The aromatic substituent at the ninth position is at 84 degrees in angle with the xanthene system.

  DOI：

  10.1023/a:1009583417391

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。
• Introduction of O-sulfonated poly(4-vinylpyrrolidonium) chloride as a polymeric and reusable catalyst for the synthesis of xanthene derivatives
  作者：Farhad Shirini、Peyman Najafi Moghadam、Simin Moayedi、Mohadeseh Seddighi

  DOI：10.1039/c4ra04915b

  日期：——

  O-Sulfonated poly(4-vinylpyrrolidonium) chloride is prepared from the reaction of poly(4-vinylpyrrolidone) [PVP], as a cheap and commercially available reagent, and neat chlorosulfonic acid at room temperature. A variety of techniques including infrared spectra (IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), X-ray diffraction (XRD), pH analysis and Hammett acidity (Ho) were used to characterize this solid acid. This polymeric reagent showed excellent catalytic activity for the synthesis of xanthene derivatives including 1,8-dioxooctahydroxanthenes, 14-aryl-14H-dibenzo[a,j] xanthenes and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones under solvent free conditions. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.

  采用廉价的市售试剂聚(4-乙烯基吡咯烷酮)[PVP]和纯氯磺酸在室温下反应制备了O-磺化聚(4-乙烯基吡咯烷酮-氯)。通过红外光谱(IR)、热重分析(TGA)、扫描电子显微镜(SEM)、X射线衍射(XRD)、pH分析和Hammett酸性(Ho)等多种技术对这种固体酸进行了表征。这种聚合物试剂在无溶剂条件下对制备包括1,8-二氧杂八氢吖啶、14-芳基-14H-二苯并[a,j]吖啶和12-芳基-8,9,10,12-四氢苯并[a]吖啶-11-酮在内的吖啶衍生物表现出优异的催化活性。产物的产率很高，反应时间短，催化剂可以重复使用多次而不会明显降低其活性。
• Introduction of a new bi-SO₃H ionic liquid based on 2,2′-bipyridine as a novel catalyst for the synthesis of various xanthene derivatives
  作者：Farhad Shirini、Masoumeh Abedini、Mohaddeseh Seddighi、Omid Goli Jolodar、Mohadeseh Safarpoor、Nikoo Langroodi、Solmaz Zamani

  DOI：10.1039/c4ra12361a

  日期：——

  1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride, [BiPy](SO3H)2Cl2 as a new ionic liquid, is prepared, characterized and used as an efficient catalyst for the promotion of the synthesis of various symmetric and asymmetric xanthene derivatives under solvent free conditions. All products were formed in excellent yields over short reaction times. Easy preparation of the catalyst, simple and easy work-up, mild

  在这项研究中，制备了1,1'-二磺基-[2,2'-联吡啶] -1,1'-氯化二氢[BiPy]（SO 3 H）2 Cl 2作为一种新型离子液体，并进行了表征和在无溶剂条件下用作促进各种对称和不对称x吨衍生物合成的有效催化剂。在较短的反应时间内，所有产品均以优异的产率形成。催化剂的易于制备，简单且容易的后处理，温和的反应条件，低成本，优异的收率和较短的反应时间是这项工作的一些优点。
• 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。