9,9-dimethyl-12-(thiophen-2-yl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one | 1093648-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9,9-dimethyl-12-(thiophen-2-yl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
• 英文别名: 9,9-dimethyl-12-thiophen-2yl-8,9,10,12-tetrahydro-benzo[a]xanthene-11-one；9,9-Dimethyl-12-(thiophen-2-yl)-8,9,10,12-tetra-hydrobenzo[a]xanthen-11-one；9,9-dimethyl-12-thiophen-2-yl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1093648-03-3
• 化学式: C₂₃H₂₀O₂S
• 分子量: 360.477
• InChiKey: YVUFEYZUUNBGCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,9-dimethyl-12-(thiophen-2-yl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.58h， 以87%的产率得到9,9-dimethyl-12-thiophen-2-yl-10,12-dihydro-8H-benzo[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：

  2-噻吩甲醛 、 5,5-二甲基-1,3-环己二酮 、 2-萘酚 在 hydroxyapatite-encapsulated γ-Fe₂O₃-supported dual acidic nanocatalyst 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以93%的产率得到9,9-dimethyl-12-(thiophen-2-yl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
  参考文献：
  名称：

  HAp封装的γ-Fe2O3负载的双酸性多相催化剂，用于高效一锅合成苯并氧杂蒽酮和3-吡喃吲哚

  摘要：

  一种新颖的方法是通过使用新合成的HAp包封了γ-Fe一锅三组分反应报道benzoxanthenone和3- pyranylindole衍生物的合成2 ö 3 -支持双酸性非均相催化剂，如可重复使用的和高效率的纳米催化剂。在该方案中，纳米催化剂的使用提供了一种绿色，有用且快速的方法，可在较短的反应时间（4-20分钟）内以优异的产率（87-96％）生成产物。催化剂的顺磁性为通过施加外部磁体分离催化剂提供了一种简单，无故障且简便的方法，并且可以在八个循环中使用，而不会显着降低催化效率。

  DOI：

  10.1002/aoc.4072

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。
• 4-Imidazol-1-yl-butane-1-sulfonic acid or a novel liquid salt? The NMR analysis and dual solvent-catalytic efficiency for one-pot synthesis of xanthenes
  作者：Nader Ghaffari Khaligh、Lim Shi Teng、Ong Chiu Ling、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1016/j.molliq.2019.01.041

  日期：2019.3

  structure of the product was investigated by the NMR analysis in CD3OD and DMSO‑d6. This work demonstrated that 4-imidazol-1-yl-butane-1-sulfonic acid could not be obtained through the above reaction and the mixture of zwitterionic (I) and ionic (II) structure is produced. The structure of the liquid salt (I + II) was characterized and analyzed by 2D NMR. Then, the dual solvent-catalytic efficiency of

  咪唑和1,4-丁烷磺酸等摩尔混合物的反应在90°C下在乙苯中进行12 h，并通过NMR分析在CD 3 OD和DMSO- d 6中研究产物的结构。这项工作表明通过上述反应不能获得4-咪唑-1-基-丁烷-1-磺酸，并且生成了两性离子（I）和离子（II）结构的混合物。通过2D NMR对液态盐（I + II）的结构进行表征和分析。然后，在温和的条件下研究了液态盐（I + II）的双溶剂催化效率，以合成多种黄嘌呤，从而在较短的反应时间内以良好的产率提供了所需的产物。研究了液态盐（I + II）的可回收性，其后三个运行的平均回收率为89％。循环使用的液态盐即使经过3次运行也没有表现出明显的催化活性损失，其结构与新鲜液态盐（I + II）相同。
• A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water
  作者：Jianjun Li、Lingmei Lu、Weike Su

  DOI：10.1016/j.tetlet.2010.02.149

  日期：2010.5

  Catalyzed by proline triflate, benzoxanthenes were obtained in good yields from the condensation of naphthols, aldehydes, and 1,3-dicarbonyl compounds in water. A possible mechanism of this reaction is proposed.

  在三氟甲磺酸脯氨酸的催化下，萘酚，醛和1,3-二羰基化合物在水中的缩合可得到高收率的苯并氧杂蒽。提出了该反应的可能机理。
• Synthesis and characterization of novel binuclear task-specific ionic liquid: an efficient and sustainable sulfonic-functionalized ionic liquid for one-pot synthesis of xanthenes
  作者：Nader Ghaffari Khaligh

  DOI：10.1007/s11164-018-3354-8

  日期：2018.7

  A new binuclear sulfonic-functionalized ionic liquid was synthesized in two steps and its dual solvent-catalytic activity was studied for the synthesis of a variety of xanthenes under mild conditions. The simple experimental and sustainable procedure, good yield of the desired products within short reaction times, and recyclability of the ionic liquid are some advantages of the present strategy, and

  分两步合成了一种新的双核磺酸官能化离子液体，并研究了其在双重溶剂催化下在温和条件下合成多种黄嘌呤的活性。简单的实验和可持续的过程，较短的反应时间内所需产物的良好收率以及离子液体的可回收性是本策略的一些优势，目前的工作表明特定任务的离子液体在有机合成中非常重要。
• An Organocatalyzed Expeditious Synthetic Route to Tetrahydrobenzo[a]xanthen-11-ones via Grinding Technique
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.2174/157017811797249308

  日期：2011.10.1

  In the present study, successful implementation of grinding technique and camphor sulphonic acid (CSA) as a catalyst, has been demonstrated for the rapid synthesis of 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11- ones at ambient temperatures, avoiding excessive/wasteful heating.

  在本研究中，成功实施了研磨技术和樟脑磺酸（CSA）作为催化剂，证明可以在常温下快速合成12-芳基-9,9-二甲基-8,9,10,12-四氢苯并[a]黄烷-11-酮，避免了过度/浪费的加热。