4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl) benzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl) benzonitrile
• 英文别名: 4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-9-yl)benzonitrile；4-(2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-1H-xanthen-9-yl)benzonitrile；4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)benzonitrile；9-(4-cyanophenyl)-3,3,6,6-tetramethyl-1,8-dioxo-octahydroxanthene；3,3,6,6-tetramethyl-9-(4-cyanophenyl)-1,8-dioxooctahydroxanthene；4-(3,3,6,6-tetramethyl-1,8-dioxo-4,5,7,9-tetrahydro-2H-xanthen-9-yl)benzonitrile
• 化学式: C₂₄H₂₅NO₃
• mdl: MFCD00521093
• 分子量: 375.467
• InChiKey: UHUDMRVJPUYKBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl) benzonitrile 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 C₂₄H₂₇NO₃
  参考文献：
  名称：

  一类新的8-羟基呫吨酮和呫吨1,8-二醇：呫吨二酮衍生物的还原

  摘要：

  摘要 目前的工作报告了一种简单、温和、有效的方案，通过使用容易获得、成本效益高、易于处理的硼氢化钠作为还原剂，将呫吨二酮还原为 8-羟基呫吨酮和呫吨1,8-二醇。得到的产物产率好到极好，反应时间短。该反应的多功能性、温和的反应条件、高产率和易于后处理的结合使得该反应值得注意。对合成的化合物进行光谱分析。此外，对四种衍生物进行了重结晶，并通过晶体学研究证实了结构。晶体结构由分子间O-H···O氢键和C-H···O弱相互作用稳定。

  DOI：

  10.1080/00397911.2022.2032756
• 作为产物：
  描述：

  4-[(4,4-Dimethyl-2,6-dioxocyclohexyl)(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)methyl]benzonitrile 在 magnesium sulfate 作用下， 以 甲醇 为溶剂， 以78%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) benzonitrile
  参考文献：
  名称：

  Diammonium Hydrogen Phosphate as a Neutral and Efficient Catalyst for Synthesis of 1,8‐Dioxo‐octahydroxanthene Derivatives in Aqueous Media

  摘要：

  A new and efficient method to synthesize a 3,3,6,6,9-aryl-l,8-dioxo-octa-hydroxanthene derivative using diammonium hydrogen phosphate as catalyst was performed in water at room temperature in a short periods.

  DOI：

  10.1080/00397910701196520

文献信息

• Ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of β-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes
  作者：Abdolkarim Zare、Ahmad Reza Moosavi-Zare、Maria Merajoddin、Mohammad Ali Zolfigol、Tahereh Hekmat-Zadeh、Alireza Hasaninejad、Ardeshir Khazaei、Mohammad Mokhlesi、Vahid Khakyzadeh、Fatemeh Derakhshan-Panah、Mohammad Hassan Beyzavi、Esmael Rostami、Azam Arghoon、Razieh Roohandeh

  DOI：10.1016/j.molliq.2011.12.012

  日期：2012.3

  the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes from β-naphthol (2 equiv.) and aldehydes (1 equiv.) in harsh conditions (120 °C) in the absence of solvent. High yields, relatively short reaction times, efficiency, generality, clean process, simple methodology, low cost, easy work-up, ease of preparation and regeneration of the catalyst and green conditions (in the synthesis of the xanthene derivatives)

  在这项工作中，新型布朗斯台德酸性离子液体三乙胺键合磺酸[Et 3 N–SO 3 H] Cl，N，N -N-二乙基-N-磺基硫代氯化铵}作为均相和绿色催化剂的效率，通用性和适用性研究了各种条件下的有机转化。在此，在[Et 3 N–SO 3H] Cl的研究：（i）由苯乙酮，醛，乙腈和乙酰氯在溶液中和在极温和的条件下（室温）合成β-乙酰氨基酮，（ii）制备1,8-二氧-八氢氧杂蒽在中等温度（80°C）下于无溶剂条件下由二甲酮（5,5-二甲基-1,3-环己二酮）（2当量）和醛（1当量）合成，以及（iii）14-芳基-14 H-二苯并[ a，jβ-萘酚（2当量）和醛（1当量）中的]黄嘌呤在苛刻条件下（120°C）且无溶剂存在。高收率，相对短的反应时间，效率，通用性，清洁的方法，简单的方法，低成本，后处理，催化剂的易于制备和再生以及绿色条件（在an吨衍生物的合成中）是该方法的优点。 [Et 3 N–SO
• Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)₂: A Route to Aryl Nitriles
  作者：Majid M. Heravi、Farhad Panahi、Nasser Iranpoor

  DOI：10.1021/acs.orglett.8b00974

  日期：2018.5.4

  A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C–O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.

  利用相对无毒的Zn（CN）2作为氰化物源，开发了一种新颖，高效的镍催化的酚类化合物镍脱氧氰化方法。2,4,6-三氯-1,3,5-三嗪与C（O）活化的酚类化合物在镍预催化剂存在下与Zn（CN）2的反应获得了芳香腈，收率很好。
• One-pot three-component synthesis of 1,8-dioxooctahydroxanthenes and 14-Aryl-14Hdibenzo[a,j]xanthenes using a new nanostructure zeolite
  作者：SEYEDEH FATEMEH HOJATI、MARYAM MOOSAVIFAR、NASRIN MOEINIEGHBALI

  DOI：10.1007/s12039-020-1736-0

  日期：2020.12

  significant advantages of the present method are high yields of products, short reaction time, easy separation of the catalyst from the reaction mixture, easy product isolation, solvent-free condition and reusability of the catalyst. Graphic abstract A new modified zeolite containing Fe nanoparticles loaded in zeolite X has been synthesized, characterized and applied in the synthesis of two series

  摘要 通过FT-IR，XRD，EDX和SEM技术合成了一种新型改性的含Fe纳米颗粒的Fe纳米沸石，并对其进行了表征，并研究了其在两个系列x吨衍生物的合成中的催化活性。我们已经描述了一种有效且新颖的方法，使用Fe-X作为一种新的可重复使用的催化剂，用于从一锅三组分缩合反应中合成1,8-二氧杂八氢氧杂蒽和14-芳基-14H-二苯并[ a，j ]氧杂蒽衍生物醛和二甲酮或β的含量-萘酚在无溶剂条件下。本方法的显着优点是产物的产率高，反应时间短，催化剂与反应混合物的分离容易，产物分离容易，无溶剂条件和催化剂的可重复使用性。 图形摘要 合成了一种新型的载有沸石X的含Fe纳米粒子的改性沸石，并对其进行了表征，并将其用于合成两个系列的x吨衍生物。
• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。
• Zinc oxide nanoparticles: A highly efficient and readily recyclable catalyst for the synthesis of xanthenes
  作者：Javad Safaei-Ghomi、Mohammad Ali Ghasemzadeh

  DOI：10.1016/j.cclet.2012.09.016

  日期：2012.11

  A novel and efficient route for the synthesis of 1,8-dioxooctahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes is described through one-pot multi-component reaction of dimedone and 2-naphthol with various aryl aldehydes using ZnO nanoparticles under solvent-free conditions. This method provides a novel and improved pathway for the synthesis of xanthenes in the terms of excellent yields, short reaction

  通过使用二甲酮和2-萘酚与各种芳基醛的一锅多组分反应，描述了一种合成1,8-二氧杂八氢氧杂蒽和14-芳基-14 H-二苯并[a，j]黄嘌呤的新颖有效途径。无溶剂条件下的ZnO纳米颗粒。就优异的产率，短的反应时间，可重复使用性和低的催化剂载量而言，该方法提供了一种新颖的和改进的用于合成黄嘌呤的途径。