3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-3-yl)-2H-xanthene-1,8(5H,9H)-dione | 329693-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-3-yl)-2H-xanthene-1,8(5H,9H)-dione
• 英文别名: 1,2,3,4,5,6,7,8-octahydro-3,3,6,6-tetramethyl-9-(pyridin-3-yl)xanthene-1,8-dione；9-(pyridine-3-yl)-1,8-dioxo-octahydroxanthene；3,3,6,6-Tetramethyl-9-pyridin-3-yl-3,4,5,6,7,9-hexahydro-1h-xanthene-1,8(2h)-dione；3,3,6,6-tetramethyl-9-pyridin-3-yl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 329693-26-7
• 化学式: C₂₂H₂₅NO₃
• mdl: MFCD00368697
• 分子量: 351.445
• InChiKey: FSXSLTZZUMNOKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(pyridin-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-3-yl)-2H-xanthene-1,8(5H,9H)-dione
  参考文献：
  名称：

  Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound

  摘要：

  N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presence of a base, the coupling reaction generates beta-keto enol ether as the major product in a polar aprotic solvent. N-Tosylhydrazone can also be converted to xanthenedione in high yields in one-pot operation under mild acidic conditions. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.02.001

文献信息

• A green and efficient procedure for one-pot synthesis of xanthenes and acridines using silica boron–sulfuric acid nanoparticles (SBSANs) as a solid Lewis-protic acid
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Somayeh Mohammadi、Habib Ollah Foroughi

  DOI：10.1007/s13738-012-0140-1

  日期：2013.4

  Silica boron–sulfuric acid nanoparticles (SBSANs) as a solid Lewis-protic acid have been found to be an efficient heterogeneous catalyst in the synthesis of xanthene and acridine derivatives. The SBSAN-catalyzed reaction between carbonyl compound (aldehyde/ketone/ethyl orthoformate) and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) for synthesis of xanthene derivatives is performed under mild conditions with the excellent isolated yield. Also, we can apply a broad scope of carbonyl compounds and amines for efficient synthesis of various acridine derivatives in the presence of SBSAN catalyst. In these multicomponent approaches the SBSAN catalyst can be reused for several times without any treatment in its catalytic activity.

  硅硼硫酸纳米颗粒（SBSANs）作为一种固态Lewis-质子酸，已被发现是合成氧杂蒽和吖啶衍生物的高效非均相催化剂。在温和条件下，通过SBSAN催化下的羰基化合物（醛/酮/原甲酸三乙酯）与5,5-二甲基-1,3-环己二酮（二甲基酮）的反应合成氧杂蒽衍生物，具有出色的分离产率。此外，我们可以在SBSAN催化剂的存在下，应用广泛的羰基化合物和胺，高效合成各种吖啶衍生物。在这些多组分方法中，SBSAN催化剂无需任何处理即可多次重复使用，其催化活性保持不变。
• 1-Butyl-3-methylimidazolium Hydrogen Sulfate [Bmim]HSO₄: An Efficient Reusable Acidic Ionic Liquid for the Synthesis of 1,8-Dioxo-Octahydroxanthenes
  作者：Khodabakhsh Niknam、Maryam Damya

  DOI：10.1002/jccs.200900098

  日期：2009.6

  1‐Butyl‐3‐methylimidazolium hydrogen sulfate [bmim]HSO4 as an acidic ionic liquid was prepared and used as a catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthenes in excellent yields and short reaction times at 80 °C. The ionic liquid was easily separated from the reaction mixture by water extraction and was recycled four times without any loss in activity.

  制备了酸性离子液体的1-丁基-3-甲基咪唑硫酸氢盐[bmim] HSO 4，并用作催化剂，在80°C下以极好的收率和短的反应时间合成了1,8-二氧-八氢氧杂蒽。通过水萃取容易将离子液体从反应混合物中分离出来，并循环四次而没有任何活性损失。
• An efficient catalytic synthesis of 1,8-dioxo-octahydroxanthene derivatives with anti-oxidant scanning
  作者：Tamer Khatab、Ahmed ElMakabaty、Zeinab M.Gamala、Ezz Kandil

  DOI：10.21608/ejchem.2018.3381.1285

  日期：2018.5.31

  Eco-friendly one pot synthesis is developed for 1,8-dioxo-octahydroxanthenes from aldehydes and dimedone using non-toxic, easily prepared and recyclable catalyst (Sm2O3/SiO2) as a silica supported rare earth element under solvent –free conditions. four of the synthesized compounds showed promising ABTS (3i, 68.7; 3b, 59.2; 3h, 50.2 inhibition%) compared with ascorbic acid.

  开发了一种环境友好的单锅合成法，从醛和双甲酮出发，使用无毒、易制备且可回收的催化剂（Sm2O3/SiO2），在无溶剂条件下合成1,8-二氧代-八氢氧蒽。其中四种合成的化合物显示出与抗坏血酸相当的ABTS自由基清除活性（3i, 68.7%；3b, 59.2%；3h, 50.2%抑制率）。
• 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。
• Pulsed laser ablated zeolite nanoparticles: A novel nano‐catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene and <i>N</i> ‐aryl‐1,8‐dioxodecahydroacridine with molecular docking validation
  作者：A.M. Abdelghany、A.A. Menazea、Mansoura A. Abd‐El‐Maksoud、Tamer K. Khatab

  DOI：10.1002/aoc.5250

  日期：2020.2

  There is an increasing interest in the synthesis of metal nanoparticles (NPs) from bulk metals using pulsed laser ablation in liquids (PLAL), as it offers an easy and simple synthesis route. In this work, zeolite NPs (molecular sieve 4A) were successfully synthesized by the PLAL technique, and characterized by X‐ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy

  使用液体中的脉冲激光烧蚀（PLAL）从块状金属合成金属纳米颗粒（NPs）的兴趣日益增加，因为它提供了一种简便的合成途径。在这项工作中，通过PLAL技术成功地合成了NPs（分子筛4A），并通过X射线衍射，扫描电子显微镜，傅立叶变换红外光谱，透射电子显微镜，场发射扫描电子显微镜和高分辨率进行了表征。透射电子显微镜。获得的数据证实了沸石的结晶相的形成。合成的催化剂（沸石分子筛4A）被用作合成of吨和a啶衍生物的有效而简便的促进剂。