3,4,6,7-Tetrahydro-9-(4-flourophenyl)-2H-xanthene-1,8(5H,9H)-dione

• 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: 3,4,6,7-Tetrahydro-9-(4-flourophenyl)-2H-xanthene-1,8(5H,9H)-dione
• 英文别名: 9-(4-Fluorophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(4-fluorophenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• 化学式: C₁₉H₁₇FO₃
• 分子量: 312.341
• InChiKey: GNTFUMYNORSNDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  4

反应信息

• 作为产物：
  描述：

  2,2'-((4-fluorophenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one) 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3,4,6,7-Tetrahydro-9-(4-flourophenyl)-2H-xanthene-1,8(5H,9H)-dione
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741

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。
• 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。
• Efficient synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by β-cyclodextrin grafted with butyl sulfonic acid in aqueous media
  作者：Kai Gong、Hualan Wang、Shuxin Wang、Ying Wang、Jinghua Chen

  DOI：10.1016/s1872-2067(15)60888-9

  日期：2015.8

  β-Cyclodextrin was functionalized with butyl sulfonic acid to give an efficient, eco-friendly catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes via the one-pot condensation of aromatic aldehydes and active methylene carbonyl compounds in aqueous media. This new methodology offers several advantages such as excellent yields, short reaction time, a simple procedure and mild reaction conditions

  β-环糊精用丁基磺酸官能化，通过芳香醛和活性亚甲基羰基化合物在水性介质中的一锅缩合反应，为合成 1,8-二氧代-八氢氧杂蒽提供了一种高效、环保的催化剂。这种新方法具有多种优势，例如收率高、反应时间短、程序简单和反应条件温和。此外，催化剂可以很容易地回收和重复使用多达五次，而不会显着降低其活性。
• CsF mediated rapid condensation of 1,3-cyclohexadione with aromatic aldehydes: Comparative study of conventional heating vs. ambient temperature
  作者：Kamalakar P. Nandre、Vijay S. Patil、Sidhanath V. Bhosale

  DOI：10.1016/j.cclet.2011.01.002

  日期：2011.7

  A mild, efficient and high yielding protocol for the synthesis of 2,2′-arylmethelene dicyclohexane-1,3-dione derivatives at room temperature and 9-aryl-1,8-dihydrooctahydroxanthene at conventional heating using cesium fluoride as a catalyst is reported. The major advantages of this reaction are excellent yield, very short reaction time and use of inexpensive catalyst.

  据报道，使用氟化铯作为催化剂，在常规加热条件下，室温下合成2,2'-芳基亚甲基二环己烷-1,3-二酮衍生物和9-芳基-1,8-二氢八氢oct吨蒽的合成反应温和，高效，高收率。 。该反应的主要优点是优异的产率，非常短的反应时间和使用廉价的催化剂。
• One-pot synthesis of new derivatives of pyran using N-halosulfonamide
  作者：Ramin Ghorbani-Vaghei、Zahra Salimi、Seyedeh Mina Malaekehpoor、Fatemeh Eslami、Samira Noori

  DOI：10.1039/c4ra04929b

  日期：——

  In this study N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide was used as a reagent for the three-component one-pot synthesis of some novel 9-aryl-9H-2,4,5,7-tetramethyl-diuracilopyrans, which has not been published before, as well as 9-aryl-3,4,6,7-tetrahydro-2H-pyran-1,8(5H,9H)-diones in excellent yields. This is obtained from the condensation of aromatic and heterocyclic aldehydes and N,N-dimethylbarbituric acid or cyclohexane-1,3-diones in ethanol at room temperature.

  本研究以N,N,N',N'-四溴苯-1,3-二磺酰胺为试剂，三组分一锅法合成了一些新型9-芳基-9H-2,4,5,7 -四甲基-二尿嘧啶，以前从未发表过，以及 9-芳基-3,4,6,7-四氢-2H-吡喃-1,8(5H,9H)-二酮，收率极佳。它是由芳香醛和杂环醛与 N,N-二甲基巴比妥酸或环己烷-1,3-二酮在乙醇中在室温下缩合而得。