9-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 879217-85-3

• 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-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-Bromophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 879217-85-3
• 化学式: C₁₉H₁₇BrO₃
• 分子量: 373.246
• InChiKey: MOUVMNUUXACZIN-UHFFFAOYSA-N

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

• 作为反应物：
  描述：

  9-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 、 5-嘧啶硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以27%的产率得到9-(4-(pyrimidin-5-yl)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：

  2,2'-((4-bromophenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one) 在 NP (natural phosphate collected from an extracted ore in Yazd, Iran) 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 9-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  天然磷酸盐是合成四酮和x吨衍生物的高效绿色催化剂

  摘要：

  摘要 通过芳族醛与1的Knoevenagel-Michael级联反应，天然磷酸酯被用作合成四酮（2-2.5 h，90–100％）和黄酮（6.5–8.5 h，84–95％）的有效和环保催化剂。 ，3-环二酮分别在水和乙醇中。与传统的化学合成方法相比，该方案具有许多优点，例如后处理简单，易于处理，催化剂无毒，稳定，成本低廉，环境友好。 图形概要

  DOI：

  10.1007/s11164-016-2603-y

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。
• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。
• Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

• 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。