9-(3-bromophenyl)-1,8-dioxo-dodecahydroxanthene | 339219-33-9

• 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-(3-bromophenyl)-1,8-dioxo-dodecahydroxanthene
• 英文别名: 9-(3-bromophenyl)-1,8-dioxooctahydroxanthene；9-(3-bromophenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 339219-33-9
• 化学式: C₁₉H₁₇BrO₃
• 分子量: 373.246
• InChiKey: PLIDJIBQOLLCGG-UHFFFAOYSA-N

物化性质

• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  间溴苯甲醛 、 1,3-环己二酮 在 1,1'-disulfo-[2,2'-bipyridine]-1,1'-diium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以98%的产率得到9-(3-bromophenyl)-1,8-dioxo-dodecahydroxanthene
  参考文献：
  名称：

  基于2,2'-联吡啶 的新型bi-SO 3 H离子液体的引入，作为合成各种x吨衍生物的新型催化剂

  摘要：

  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。

  DOI：

  10.1039/c4ra12361a

文献信息

• 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。
• Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1016/j.dyepig.2012.06.022

  日期：2012.12

  A mild, simple and convenient procedure for the synthesis of xanthene derivatives is described via three component condensation of aldehydes with 2-naphthol, 1,3-cyclohexanedione and/or a mixture of 2-naphthol and 1,3-cyclohexanediones using succinimide-N-sulfonic acid as an efficient, cheap and readily synthesis catalyst under solvent-free conditions. The structures of the products were characterized

  通过醛与2-萘酚，1,3-环己二酮和/或2-萘酚和1,3-环己二酮的混合物使用琥珀酰亚胺-N进行三组分缩合，描述了一种温和，简单，方便的合成x吨衍生物的方法。-磺酸在无溶剂条件下作为一种高效，廉价且易于合成的催化剂。产品的结构通过其物理常数，与真实样品的比较以及IR，1 H NMR和13 C NMR光谱进行表征。本方法提供了许多优点，例如高收率，简单的方法，低成本，短的反应时间，无溶剂和温和的反应条件以及使用可重复使用的催化剂。
• Use of nanoporous Na+-montmorillonite sulfonic acid (SANM) as an eco-benign, efficient and reusable solid acid catalyst for the one-pot synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes and 1,8-dioxo-dodecahydroxanthene derivatives
  作者：Farhad Shirini、Manouchehr Mamaghani、Seyyed Vahid Atghia

  DOI：10.1007/s13738-012-0174-4

  日期：2013.6

  Nanoporous Na+-montmorillonite sulfonic acid was found to be an efficient and green catalyst for the synthesis of various 14-aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-dodecahydroxanthene derivatives by the reaction of aldehydes with 2-naphthol and 1,3-cyclohexanedione, respectively. This novel synthetic method has the advantages of high yields, short reaction times and recyclability of the catalyst, simplicity and easy workup compared to the conventional methods reported in the literature.

  纳米多孔Na+-蒙脱石磺酸被发现是一种高效且绿色的催化剂，用于合成多种14-芳基-14H-二苯并[a,j]黄酮和1,8-二氧代-十二氢羟基黄酮衍生物，该反应是通过醛与2-萘醇和1,3-环己二酮的反应进行的。这种新颖的合成方法具有高产率、反应时间短以及催化剂可回收利用的优点，比文献中报道的传统方法更为简单且易于操作。
• Copper iodide nanoparticles on poly(4-vinylpyridine): A new and efficient catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions
  作者：JALAL ALBADI、MOSADEGH KESHAVARZ、MASOUMEH ABEDINI、MOLOUD KHOSHAKHLAGH

  DOI：10.1007/s12039-013-0368-z

  日期：2013.3

  Poly(4-vinylpyridine)-supported nanoparticles of copper(I) iodide is reported as a new, efficient and recyclable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst can be recovered by simple filtration and recycled up to 10 consecutive runs without losing of its efficiency.

  报道了聚(4-乙烯基吡啶)负载的碘化亚铜纳米粒子作为一种新型、高效和可循环使用的催化剂，用于无溶剂条件下合成1,8-二氧代八氢氧杂蒽。该催化剂可以通过简单过滤回收，并且可以连续循环使用10次而不损失其催化效率。