1H-占吨-1,8(2H)-二酮,3,4,5,6,7,9-六氢-9-(4-甲氧苯基)- | 109399-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1H-占吨-1,8(2H)-二酮,3,4,5,6,7,9-六氢-9-(4-甲氧苯基)-
• 英文名称: 9-(4-methoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-methoxyphenyl)-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione；9-(4-methoxy-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione；9-(4-Methoxy-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthen-1,8-dion；9-<4-Methoxy-phenyl>-1.2.3.4.5.6.7.8-octahydro-xanthendion-(1.8)；9-(4-methoxyphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 109399-70-4
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: GRWGJVLJPBIKNT-UHFFFAOYSA-N

物化性质

• 熔点：
  241-243 °C(Solv: ethanol (64-17-5))
• 沸点：
  532.5±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：

  1H-占吨-1,8(2H)-二酮,3,4,5,6,7,9-六氢-9-(4-甲氧苯基)- 在 氯磺酸 作用下， 以 乙醇 为溶剂， 生成 9-[4-methoxy-3-(1-pyrrolidinylsulfonyl)phenyl]-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-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
• 作为产物：
  描述：

  2,2'-((4-methoxyphenyl)methylene) dicyclohexane-1,3-dione 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以64%的产率得到1H-占吨-1,8(2H)-二酮,3,4,5,6,7,9-六氢-9-(4-甲氧苯基)-
  参考文献：
  名称：

  Sachar, Anand; Gupta, Poonam; Gupta, Shallu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 8, p. 1187 - 1194

  摘要：

  DOI：

文献信息

• Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

• Introduction of a trinuclear manganese(<scp>iii</scp>) catalyst on the surface of magnetic cellulose as an eco-benign, efficient and reusable novel heterogeneous catalyst for the multi-component synthesis of new derivatives of xanthene
  作者：Pouya Ghamari kargar、Ghodsieh Bagherzade、Hossein Eshghi

  DOI：10.1039/d0ra09420j

  日期：——

  recyclability of the catalyst, easy workup, and the ability to sustain a variety of functional groups, which give economical as well as ecological rewards. Also, the synthesized catalyst was used as a recyclable trinuclear catalyst in alcohol oxidation reactions at 40 °C. The magnetic catalyst activity of Fe3O4@NFC@NNSM-Mn(III) could be attributed to the synergistic effects of the catalyst Fe3O4@NFC@NNS-Mn(III)

  在这项工作中，成功制备了新型三核锰催化剂Fe 3 O 4 @NFC@NNSM-Mn( III )，并通过不同的技术（包括FT-IR、XRD、TEM、SEM、EDX、VSM和ICP 分析。已有报道使用磁性催化剂合成黄嘌呤衍生物。本方法的关键潜在兴趣包括反应时间短、产率高、催化剂的可回收性、易于后处理以及维持多种官能团的能力，这提供了经济和生态回报。此外，合成的催化剂还可作为可回收的三核催化剂用于40℃下的醇氧化反应。 Fe 3 O 4 @NFC@NNSM-Mn( III ) 的磁性催化活性可能归因于催化剂 Fe 3 O 4 @NFC@NNS-Mn( III ) 与三聚氰胺的协同效应。采用可持续且安全的低温、使用环保溶剂、无需使用任何添加剂以及催化剂至少连续六次运行的长期稳定性和磁性可回收性是当前绿色化学协议的优势。该方案是一种良性、环境友好的杂环合成方法。
• Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives
  作者：Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi、Mohadeseh Seddighi、Omid Goli Jolodar

  DOI：10.1007/s11164-014-1905-1

  日期：2015.11

  1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.

  1,8-二氧杂-八氢化咕吨类化合物可通过醛与1,3-环己二酮和/或双甲酮在新型高效的N-磺化DABCO催化剂作用下缩合反应制得。该试剂同样能高效催化醛与巴比妥酸的缩合反应，生成5-芳亚甲基-嘧啶-2,4,6-三酮。产物结构通过其红外光谱、核磁共振氢谱和碳谱得以表征。本方法具有多种优势，如催化剂制备与处理简便、产率高、操作简单且环保、成本低、反应时间短、后处理简便，以及可在无溶剂条件下或使用水作为绿色溶剂的情况下预先进行反应。
• Magnetic Fe–Cr–Ni oxide alloy nano-belts prepared from the chemical decomposition of a stainless steel screw (a top-down approach): an efficient and cheap catalyst for multicomponent reactions
  作者：Milad Kazemnejadi、Zeinab Sharafi、Boshra Mahmoudi、Atefeh Zeinali、Mohammad Ali Nasseri

  DOI：10.1007/s13738-019-01814-z

  日期：2020.4

  A new, cheap, and accessible method has been used for the preparation of nano-belts from the chemical decomposition (top-down approach) of a cheap stainless steel screw and found as an efficient magnetically recyclable nanocatalyst for the preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild reaction conditions. The nano-belts, Fe–Cr–Ni oxide alloy, was prepared in a two-step synthesis and characterized with various instrumental methods. Due to magnetic property of the screw (a ferritic-alloy), the resultant nano-belts is magnetic. Magnetic Fe–Cr–Ni alloy nano-belts were applied toward efficient preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild conditions. The catalyst could be readily recovered and recycled for several consecutive runs, while it suffers from a very low metal leaching and subsequently efficiency drop.

  一种新的、廉价且易得的方法已被用于从廉价不锈钢螺丝的化学分解（自上而下的方法）中制备纳米带，并发现其在温和反应条件下作为高效的磁性可回收纳米催化剂，用于喹啉和1,8-二氧杂-八氢氧杂蒽的制备。这种纳米带，即Fe–Cr–Ni氧化物合金，是通过两步合成法制备的，并使用多种仪器方法进行了表征。由于螺丝（一种铁素体合金）的磁性特性，所得纳米带也具有磁性。磁性Fe–Cr–Ni合金纳米带在温和条件下被应用于高效制备喹啉和1,8-二氧杂-八氢氧杂蒽。该催化剂可以轻易地回收并在多次连续运行中循环使用，同时金属溶出现象极少，因此催化效率几乎不会下降。
• A Green and Efficient Synthesis of 9-Aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using a Task-Specific Ionic Liquid as Dual Catalyst and Solvent
  作者：Jingjun Ma、Xin Zhou、Xiaohuan Zang、Chun Wang、Zhi Wang、Jingci Li、Qing Li

  DOI：10.1071/ch06225

  日期：——

  A green and efficient method for the preparation of 9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione has been developed using functionalized ionic liquids as a catalyst and a reaction medium. The nature of both the counter anion and cation influence the catalytic performance of the ionic liquids. The ionic liquid can be recycled and reused without apparently loss of activity.

  以功能化离子液体为催化剂和反应介质，开发了一种制备 9-芳基-3,4,5,6,7,9-六氢-1H-呫吨-1,8(2H)-二酮的绿色高效方法。阴阳离子的性质会影响离子液体的催化性能。离子液体可以回收和重复使用，而不会明显丧失活性。