9-(3-methoxyphenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-dione | 382166-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 9-(3-methoxyphenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-dione
• 英文别名: 9-(3-methoxyphenyl)-1,8-dioxo-dodecahydroxanthene；9-(3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(3-methoxyphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 382166-65-6
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: JTZGFQFVCGPXND-UHFFFAOYSA-N

物化性质

• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(3-methoxyphenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-dione 在 氯磺酸 作用下， 生成 Benzenesulfonyl chloride,2-methoxy-4-(2,3,4,5,6,7,8,9-octahydro-1,8-dioxo-1H-xanthen-9-yl)-
  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
• 作为产物：
  描述：

  1,3-环己二酮 在 哌啶 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 生成 9-(3-methoxyphenyl)-2,3,4,5,6,7-hexahydro-2H-xanthene-1,8-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

• 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。
• Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1016/j.dyepig.2012.06.022

  日期：2012.12

  A mild, simple and convenient procedure for the synthesis of xanthene derivatives is described via three component condensation of aldehydes with 2-naphthol, 1,3-cyclohexanedione and/or a mixture of 2-naphthol and 1,3-cyclohexanediones using succinimide-N-sulfonic acid as an efficient, cheap and readily synthesis catalyst under solvent-free conditions. The structures of the products were characterized

  通过醛与2-萘酚，1,3-环己二酮和/或2-萘酚和1,3-环己二酮的混合物使用琥珀酰亚胺-N进行三组分缩合，描述了一种温和，简单，方便的合成x吨衍生物的方法。-磺酸在无溶剂条件下作为一种高效，廉价且易于合成的催化剂。产品的结构通过其物理常数，与真实样品的比较以及IR，1 H NMR和13 C NMR光谱进行表征。本方法提供了许多优点，例如高收率，简单的方法，低成本，短的反应时间，无溶剂和温和的反应条件以及使用可重复使用的催化剂。
• 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。
• Copper iodide nanoparticles on poly(4-vinylpyridine): A new and efficient catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions
  作者：JALAL ALBADI、MOSADEGH KESHAVARZ、MASOUMEH ABEDINI、MOLOUD KHOSHAKHLAGH

  DOI：10.1007/s12039-013-0368-z

  日期：2013.3

  Poly(4-vinylpyridine)-supported nanoparticles of copper(I) iodide is reported as a new, efficient and recyclable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst can be recovered by simple filtration and recycled up to 10 consecutive runs without losing of its efficiency.

  报道了聚(4-乙烯基吡啶)负载的碘化亚铜纳米粒子作为一种新型、高效和可循环使用的催化剂，用于无溶剂条件下合成1,8-二氧代八氢氧杂蒽。该催化剂可以通过简单过滤回收，并且可以连续循环使用10次而不损失其催化效率。
• 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。