9,9‐dimethyl‐12‐styryl‐9,10‐dihydro‐8H‐benzo[a]xanthen‐11(12H)‐one | 1187642-10-9

• 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‐styryl‐9,10‐dihydro‐8H‐benzo[a]xanthen‐11(12H)‐one
• 英文别名: 9,9-dimethyl-12-styryl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one；9,9-dimethyl-12-styryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• CAS: 1187642-10-9
• 化学式: C₂₇H₂₄O₂
• 分子量: 380.486
• InChiKey: YJVKFHNNFWQLCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 肉桂醛 、 2-萘酚 在 polyvinylpolypyrrolidone supported triflic acid 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以85%的产率得到9,9‐dimethyl‐12‐styryl‐9,10‐dihydro‐8H‐benzo[a]xanthen‐11(12H)‐one
  参考文献：
  名称：

  聚乙烯基聚吡咯烷酮负载的三氟甲磺酸（PVPP.OTf）；一种高效且可回收的多相催化剂，用于一锅浓缩β-萘酚，醛和环状1,3-二羰基化合物

  摘要：

  聚乙烯吡咯烷酮三氟甲磺酸乙烯酯（PVPP.OTf）被发现是可回收的非均相催化剂，用于在回流条件下以良好的收率很好地合成β-萘酚，醛和环状1,3-二羰基化合物。从绿色化学的观点来看，这些催化缩合具有优点。PVPP.OTf催化剂是空气稳定的，具有成本效益的，易于处理的，易于与反应产物分离的，并且以极高的纯度回收后可直接重复使用。

  DOI：

  10.1007/s11164-013-1521-5

文献信息

• An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition
  作者：Ganesh Chandra Nandi、Subhasis Samai、Ram Kumar、M.S. Singh

  DOI：10.1016/j.tet.2009.06.024

  日期：2009.8

  Indium(III) chloride catalyzed one-pot synthesis of 12-aryl/alkyl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one and 8,10-dimethyl-12-aryl-8,12-dihydro-7-oxa-8,10-diazabenzo[a]anthracene-9,11-dione derivatives have been achieved by three component cyclocondensation of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl compounds under solvent free condition in high yields. P2O5 too has been found as an effective

  氯化铟（III）催化一锅合成12-芳基/烷基-8,9,10,12-四氢苯并[ a ]氧杂蒽-11-one和8,10-二甲基-12-芳基-8,12-二氢通过醛，β-萘酚和环状1,3-二羰基化合物在无溶剂条件下的三组分环缩合，可以高产率获得-7-氧杂-8,10-二氮杂苯并[ a ]蒽-9,11-二酮衍生物。还发现P 2 O 5是实现该转化的有效催化剂。
• Alum-Catalyzed Domino Synthesis of 12-Substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones Under Solvent-Free Conditions
  作者：Rajan Kumar Sharma、Rajni Khajuria、Kamal K. Kapoor

  DOI：10.1080/00397911.2014.935794

  日期：2014.12.17

  Alum is found to catalyze efficiently the one-pot, three-component condensation of aldehydes, alpha/beta-naphthol, and dimedone to afford various 12-substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones in excellent yields. The use of alum catalyst and the solvent-free conditions make this method simple, convenient, eco-friendly, and cost-effective.
• Fe3O4 nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones
  作者：Davood Habibi、Sharif Kaamyabi、Hasan Hazarkhani

  DOI：10.1016/s1872-2067(14)60238-2

  日期：2015.3

  A simple and efficient method for the synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[alpha]xanthen-11(12)-one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes with 2-naphthol and dimedone using Fe3O4 magnetic nanoparticles (MNPs) as a heterogeneous catalyst under solvent-free conditions at 90-110 degrees C. The experimental procedure is very simple, the products are formed in high yields and the catalyst is easily separated by applying an external magnetic field. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• Ag-TiO2 Nanoparticles-catalyzed Three-component Synthesis of 12-aryl- 8,9,10,12-tetrahydrobenzo[a]-Xanthen-11-ones in Aqueous Medium
  作者：Seyed Mohammad Vahdat、Mahsa Lotfi Omran、Farhosh Kiani Barforosh

  DOI：10.2174/1386207325666220104110754

  日期：2022.10

  Background: Ag-TiO2 nanoparticles catalyzed synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-ones have been enhanced via a three-component one-pot reaction betweenβ-naphthol, several aldehydes and dimedone in H2O at room temperature. Xanthenes are essential intermediates in chemistry owing to their vast difference in biological activity. Methods: This process offered significant advantages containing appropriate cost efficiency, low amount of the catalyst, application of low-cost available Ag-TiO2 nanoparticles catalyst, purification of the product by non-chromatographic method, easy process, good atom economy, simple isolation and reusability of nanocatalyst. Result: Ag-TiO2 nanoparticles catalyst shows easy access to Xanthenes with appropriate yields in short reaction time and purity. This nanoparticles catalyst was recycled and recovered by easy filtration and was reused up to five times with only an unimportant loss in its catalytic efficacy. Conclusion: This method achieves to have a numerous scope relating to the difference in the aldehydes. Correspondingly, the attractiveness of this research was that H2O was the only by-product.