3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 155333-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 3,3,6,6-tetramethyl-9-(1-naphthyl)-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthene；3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-2H-xanthene-1,8(5H,9H)-dione；9-(naphthalen-1-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione；3,3,6,6-Tetramethyl-9-(naphthalen-1-YL)-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione；3,3,6,6-tetramethyl-9-naphthalen-1-yl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 155333-59-8
• 化学式: C₂₇H₂₈O₃
• mdl: MFCD00588639
• 分子量: 400.518
• InChiKey: IKGWFQIPTRGDHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  577.4±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 氯磺酸 作用下， 以82%的产率得到4-(3,3,6,6-Tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-naphthalene-1-sulfonyl chloride
  参考文献：
  名称：

  Cremlyn, Richard J.; Saunders, David, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 81, # 1-4, p. 73 - 82

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-(naphthalen-1-ylmethylene)bis(3-hydroxy-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 3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-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 Self-Assembled Trigonal Prismatic Molecular Vessel for Catalytic Dehydration Reactions in Water
  作者：Paramita Das、Atul Kumar、Prodip Howlader、Partha Sarathi Mukherjee

  DOI：10.1002/chem.201702263

  日期：2017.9.12

  A water‐soluble Pd6 trigonal prism (A) was synthesized by two‐component coordination‐driven self‐assembly of a PdII 90° acceptor with a tetraimidazole donor. The walls of the prism are constructed by three conjugated aromatic building blocks, which means that the confined pocket of the prism is hydrophobic. In addition to the hydrophobic cavity, large product egress windows make A an ideal molecular

  通过Pd II 90°受体与四咪唑供体的两组分配位驱动自组装合成了水溶性Pd 6三角棱镜（A）。棱镜的壁由三个共轭芳族结构块构成，这意味着棱镜的受限腔是疏水的。除了疏水腔外，大的产品出口窗口还使A一个理想的分子容器，可以在水性介质中的有限纳米空间中催化其他挑战性的假多组分脱水反应。这项研究是通过使用超分子分子容器微调反应条件来选择性生成中间四酮和黄嘌呤的尝试。而且，在相似的反应条件下，在不存在A的情况下，脱水产物的收率差或无收率，都支持了桶的密闭空间在水中促进这种反应的能力。此外，我们专注于锚定在Pd II配位结构中的基于四苯基乙烯的四咪唑单元的刚性化；在有水的情况下使依赖于阴离子的聚集诱导的发射成为可能。
• Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes
  作者：Zahra Abdi Piralghar、Mohammad Mahmoodi Hashemi、Ali Ezabadi

  DOI：10.2174/1386207321666180828092546

  日期：2018.11.15

  and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N', N'-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. MATERIALS AND METHODS Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin

  目的和目的在这项工作中，我们从N，N，N'，N'-四甲基乙二胺与氯磺酸的反应中合成并表征了一种新型的布朗斯台德酸性离子液体，并探索了其在1，8-二氧-八氢氧杂蒽合成中的催化活性。材料与方法使二甲酮，芳基醛和作为催化剂的离子液体在无溶剂条件下反应。通过薄层色谱法（乙酸乙酯/正己烷＝ 1/5）监测反应的进行。通过与文献报道的比较，将所有产物表征为其光谱数据和熔点的基础。结果制得的离子液体已成功用于1的合成 在无溶剂条件下，芳基醛与二甲酮在120°C的反应中，高至高收率的8-二氧杂八氢氧杂蒽。结论这项研究表明该催化剂在无溶剂条件下对1，8-二氧-八氧杂蒽的合成具有令人印象深刻的作用。
• Reaction in Dry Media: Silica Gel Supported Ferric Chloride Catalyzed Synthesis of 1,8-Dioxo-octahydroxanthene Derivatives
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/10426500802066096

  日期：2008.11.7

  3 -SiO 2 as an efficient and heterogeneous catalyst under microwave irradiation and thermal conditions. This method has the advantages of high yields, cleaner reactions, efficient and cost-effective method, simple methodology, short reaction times, easy workup, and greener conditions.

  在此，我们描述了一种在微波辐射和热条件下，在 FeCl 3 -SiO 2 作为高效多相催化剂的情况下，通过二甲酮和取代苯甲醛缩合制备 1,8-二氧代-八氢氧杂蒽衍生物的绿色程序. 该方法具有收率高、反应更清洁、方法高效且经济、方法简单、反应时间短、后处理容易、条件更环保等优点。
• Carbon Nanotube-Supported Butyl 1-Sulfonic Acid Groups as a Novel and Environmentally Compatible Catalyst for the Synthesis of 1,8-Dioxo-octahydroxanthenes
  作者：Parvanak Keveh Boroujeni、Zahra Heidari、Reza Khalifeh

  DOI：10.17344/acsi.2016.2291

  日期：2016.9.15

  novel multiwalled carbon nanotube catalyst with -SO3H functional groups was easily prepared from its starting materials and used as an efficient heterogeneous catalyst for one-pot Knoevenagel condensation, Michael addition, and cyclodehydration of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) with various aromatic aldehydes. Using this method 1,8-dioxo-octahydroxanthenes were obtained in excellent yields

  可以轻松地从其原料轻松制备具有-SO3H官能团的新型多壁碳纳米管催化剂，并用作一锅Knoevenagel缩合，迈克尔加成反应和5,5-二甲基-1,3-环己二酮环脱水的有效多相催化剂（二甲基二酮）和各种芳香醛。使用该方法，在室温下以优异的产率获得了1,8-二氧-八氧杂蒽。本方法在反应温度，反应时间，后处理容易，收率高以及催化剂的回收容易方面是优异的。
• Synthesis of Kaolin/Ag Nanocomposite as an Efficient and Versatile Reagent for the Synthesis of 1,8-Dioxo-Octahydroxanthene Derivatives
  作者：Bahareh Sadeghi、Saeedeh Hashemian

  DOI：10.1080/15533174.2013.776598

  日期：2014.3.16

  Kaolin/Ag nanocomposite was synthesized in a nano reactor by the calcination of the precursor at high temperature, and shown to efficiently catalyze 1,8-dioxo-octahydroxanthene synthesis via condensation of aromatic aldehydes and 5,5-dimethyl-1,3- cyclohexanedione under mild reaction conditions in good to excellent yields.

  高岭土/ Ag纳米复合材料是在高温下通过前驱体的高温煅烧在纳米反应器中合成的，并显示可通过芳族醛与5,5-二甲基-1,3-环己烷二酮的缩合有效催化1,8-二氧-八氢氧杂蒽的合成在温和的反应条件下，收率良好。