9-ethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 19744-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-ethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-ethyl-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydroxanthene-1,8-dione；9-ethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione；9-Aethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthen-1,8-dion；9-ethyl-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 19744-82-2
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: AWYRSFOUNCQZNV-UHFFFAOYSA-N

物化性质

• 熔点：
  132.8-133.5 °C
• 沸点：
  430.6±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-ethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到2,2,7,7-tetramethyl-1,2,3,6,7,8-hexahydro-cinnolino[5,4,3-cde]cinnoline
  参考文献：
  名称：

  New domino reaction for the selective synthesis of tetracyclic cinnolino[5,4,3-cde]cinnolines

  摘要：

  描述了一种新的多米诺反应，用于高选择性合成四环辛烯[5,4,3-cde]辛烯，采用立体控制。在该反应中，使用含有脂肪基团（R1）的烯烃会生成辛烯[5,4,3-cde]辛烯，而含有芳基团（R1）的烯烃则会生成N-氨基-1,8-二氧代荧烯。

  DOI：

  10.1039/b817930a
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 盐酸 、 乙醇 作用下， 生成 9-ethyl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  醛的甲酮衍生物。

  摘要：

  DOI：

  10.1021/jo01171a014

文献信息

• Silica-supported Phosphomolybdic Acid-catalyzed Efficient Synthesis of 1,8-Dioxooctahydroxanthene and Tetrahydrochromene Derivatives
  作者：Biswanath Das、Martha Krishnaiah、Keetha Laxminarayana、Kongara Damodar、Duddukuri Nandan Kumar

  DOI：10.1246/cl.2008.1000

  日期：2008.9.5

  Silica-supported phosphomolybdic acid was found to be an efficient heterogeneous catalyst for the synthesis of 1,8-dioxooctahydroxanthenes from aldehydes and dimedone and of tetrahydrochromenes fro...

  发现二氧化硅负载的磷钼酸是一种有效的多相催化剂，可用于从醛和二甲酮合成 1,8-二氧代辛基羟基氧杂蒽以及从...
• A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water
  作者：Jianjun Li、Lingmei Lu、Weike Su

  DOI：10.1016/j.tetlet.2010.02.149

  日期：2010.5

  Catalyzed by proline triflate, benzoxanthenes were obtained in good yields from the condensation of naphthols, aldehydes, and 1,3-dicarbonyl compounds in water. A possible mechanism of this reaction is proposed.

  在三氟甲磺酸脯氨酸的催化下，萘酚，醛和1,3-二羰基化合物在水中的缩合可得到高收率的苯并氧杂蒽。提出了该反应的可能机理。
• Zn[(L)Proline]₂: an eligible candidate for the synthesis of xanthenediones in water
  作者：Mazaahir Kidwai、Arti Jain

  DOI：10.1002/aoc.2895

  日期：2012.10

  An efficient route for the condensation of aldehydes with dimedone in the presence of Zn[(L)Proline]2 in water has been reported. Hydrophilicity of the catalyst is the main attribute of this reaction. The water‐mediated reaction using catalytic amounts of recyclable catalyst avoids the use of expensive, corrosive reagents and toxic solvents and provides operational simplicity. Moreover, column chromatography

  已经报道了在水中Zn [（L）脯氨酸] 2存在下醛与二甲酮缩合的有效途径。催化剂的亲水性是该反应的主要属性。使用催化量的可循环催化剂的水介导反应避免了使用昂贵的腐蚀性试剂和有毒溶剂，并简化了操作。此外，由于粗产物本身非常纯净，因此不需要柱色谱和产物重结晶，因此可以用于大规模的目标导向合成。版权所有©2012 John Wiley＆Sons，Ltd.
• Efficient Organocatalytic Synthesis of 1,8-Dioxo-octahydroxanthenes
  作者：Biswanath Das、J. Kashanna、Rathod Aravind Kumar、Paramesh Jangili

  DOI：10.1080/00397911.2011.571804

  日期：2012.10

  L-Proline has been used as an organocatalyst for an efficient synthesis of 1,8-dioxo-octahydroxanthenes by treatment of aldehydes (aromatic, heteroaromatic, and aliphatic) with 5,5-dimethyl-1,3-cyclohexanedione. Three new compounds have been prepared.
• Neat synthesis of octahydroxanthene-1,8-diones, catalyzed by silicotungstic acid as an efficient reusable inorganic catalyst
  作者：A. Davoodnia、S. Basafa、N. Tavakoli-Hoseini

  DOI：10.1134/s107036321605025x

  日期：2016.5

  In this article, the first use of silicotungstic acid (H4SiW12O40) as a catalyst for the synthesis of octahydroxanthene-1,8-diones by the reaction of 5,5-dimethylcyclohexane-1,3-dione (dimedone) with various aldehydes under thermal solvent-free conditions is described. The obtained results showed that the catalyst has a high catalytic activity, and the desired products were obtained in high yields. Moreover, the catalyst was found to be reusable, and a considerable catalytic activity still could be achieved after the fifth run. Easy work-up and avoidance of using harmful organic solvents are the other advantages of this simple procedure.