12-(3-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1177458-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 12-(3-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 12-(3-Bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(3-bromophenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1177458-70-6
• 化学式: C₂₅H₂₁BrO₂
• 分子量: 433.345
• InChiKey: YAIYZKIFJPKLNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-(3-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以86%的产率得到12-(3-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thione
  参考文献：
  名称：

  Synthesis of novel 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thiones and evaluation of their biocidal effects

  摘要：

  Novel 12-aryl-8,9,10,12-tetrahydrobenzolakanthene-11-thiones have been synthesized in high yields by treatment of the corresponding oxo analogs with Lawesson's reagent. The structure has been confirmed by X-ray analysis. The compounds were tested for in vitro antifungal activity against Rhizoctonia bataticola, Sclerotium rolfsii, Fusarium oxysporum and Alternaria porii. The compounds exhibited moderate to good activity against all pathogens. Insecticidal activity of these compounds against Spodoptera litura was observed to be comparable to commercial pyrethroid insecticide, cypermethrin. The urease inhibitory activity has also been studied. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.025
• 作为产物：
  描述：

  间溴苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 2-萘酚 在 Sb(V) functionalized cellulose on Fe₃O₄ core of a core-shell nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以95%的产率得到12-(3-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  Fe3O4@纳米纤维素/Sb(V)作为独特的生物基纳米催化剂高效合成四氢苯并[a]xanthen-11-ones

  摘要：

  发表于国际有机制剂和程序：有机合成新期刊（印刷前，2022 年）

  DOI：

  10.1080/00304948.2022.2113720

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。
• Rapid, efficient and solvent-free synthesis of (un)symmetrical xanthenes catalyzed by recyclable sulfated polyborate
  作者：Manisha S. Patil、Amey V. Palav、Chetan K. Khatri、Ganesh U. Chaturbhuj

  DOI：10.1016/j.tetlet.2017.06.027

  日期：2017.7

  straightforward approach to the synthesis of 1,8-dioxo-octahydroxanthenes, 14-phenyl-14H-dibenzo[a,j]xanthene and tetrahydrobenzoxanthene-11-ones under solvent-free conditions using sulfated polyborate as a highly efficient catalyst. The procedure offers several advantages including cleaner reaction profile, mild reaction condition, economic, recyclable and environmentally benign catalyst, high yields, simple

  本研究描述了一种在无溶剂条件下使用硫酸盐快速合成1,8-二氧-八氢氧杂蒽，14-苯基-14 H-二苯并[ a，j ]氧杂蒽和四氢苯并氧杂蒽-11的快速，简单和直接的方法。多硼酸盐作为高效催化剂。该方法具有几个优点，包括更清洁的反应曲线，温和的反应条件，经济，可循环使用和对环境无害的催化剂，高收率，简单的实验和后处理程序。尽管非萃取性后处理/纯化以及催化剂的可重复使用性使该方法在经济上可大规模使用。
• Synthesis of Quinolines, Spiro[4<i>H</i>-pyran-oxindoles] and Xanthenes Under Solvent-Free Conditions
  作者：Farzaneh Mohamadpour、Malek Taher Maghsoodlou、Mojtaba Lashkari、Reza Heydari、Nourallah Hazeri

  DOI：10.1080/00304948.2019.1653126

  日期：2019.9.3

  Green multi-component domino reactions (MCRs)1–7 for the synthesis of fine chemicals have attracted much recent interest.8–9 Quinolines, spiro[4H-pyran-oxindoles] and xanthenes are reported as havi...

  用于合成精细化学品的绿色多组分多米诺反应 (MCR)1-7 最近引起了广泛关注。8-9 喹啉、螺 [4H-吡喃-羟吲哚] 和呫吨据报道具有...
• 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。