9-(4-cyanophenyl)-1,8-dioxo-dodecahydroxanthene | 914621-01-5

• 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: 9-(4-cyanophenyl)-1,8-dioxo-dodecahydroxanthene
• 英文别名: 4-(1,8-Dioxo-2,3,4,5,6,7,8,9-octahydro-1h-xanthen-9-yl)benzonitrile；4-(1,8-dioxo-3,4,5,6,7,9-hexahydro-2H-xanthen-9-yl)benzonitrile
• CAS: 914621-01-5
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: BZUYMLIEKWRNCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(bis(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl)benzonitrile 在 NP (natural phosphate collected from an extracted ore in Yazd, Iran) 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 9-(4-cyanophenyl)-1,8-dioxo-dodecahydroxanthene
  参考文献：
  名称：

  天然磷酸盐是合成四酮和x吨衍生物的高效绿色催化剂

  摘要：

  摘要 通过芳族醛与1的Knoevenagel-Michael级联反应，天然磷酸酯被用作合成四酮（2-2.5 h，90–100％）和黄酮（6.5–8.5 h，84–95％）的有效和环保催化剂。 ，3-环二酮分别在水和乙醇中。与传统的化学合成方法相比，该方案具有许多优点，例如后处理简单，易于处理，催化剂无毒，稳定，成本低廉，环境友好。 图形概要

  DOI：

  10.1007/s11164-016-2603-y

文献信息

• Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1016/j.dyepig.2012.06.022

  日期：2012.12

  A mild, simple and convenient procedure for the synthesis of xanthene derivatives is described via three component condensation of aldehydes with 2-naphthol, 1,3-cyclohexanedione and/or a mixture of 2-naphthol and 1,3-cyclohexanediones using succinimide-N-sulfonic acid as an efficient, cheap and readily synthesis catalyst under solvent-free conditions. The structures of the products were characterized

  通过醛与2-萘酚，1,3-环己二酮和/或2-萘酚和1,3-环己二酮的混合物使用琥珀酰亚胺-N进行三组分缩合，描述了一种温和，简单，方便的合成x吨衍生物的方法。-磺酸在无溶剂条件下作为一种高效，廉价且易于合成的催化剂。产品的结构通过其物理常数，与真实样品的比较以及IR，1 H NMR和13 C NMR光谱进行表征。本方法提供了许多优点，例如高收率，简单的方法，低成本，短的反应时间，无溶剂和温和的反应条件以及使用可重复使用的催化剂。
• Use of nanoporous Na+-montmorillonite sulfonic acid (SANM) as an eco-benign, efficient and reusable solid acid catalyst for the one-pot synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes and 1,8-dioxo-dodecahydroxanthene derivatives
  作者：Farhad Shirini、Manouchehr Mamaghani、Seyyed Vahid Atghia

  DOI：10.1007/s13738-012-0174-4

  日期：2013.6

  Nanoporous Na+-montmorillonite sulfonic acid was found to be an efficient and green catalyst for the synthesis of various 14-aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-dodecahydroxanthene derivatives by the reaction of aldehydes with 2-naphthol and 1,3-cyclohexanedione, respectively. This novel synthetic method has the advantages of high yields, short reaction times and recyclability of the catalyst, simplicity and easy workup compared to the conventional methods reported in the literature.

  纳米多孔Na+-蒙脱石磺酸被发现是一种高效且绿色的催化剂，用于合成多种14-芳基-14H-二苯并[a,j]黄酮和1,8-二氧代-十二氢羟基黄酮衍生物，该反应是通过醛与2-萘醇和1,3-环己二酮的反应进行的。这种新颖的合成方法具有高产率、反应时间短以及催化剂可回收利用的优点，比文献中报道的传统方法更为简单且易于操作。
• Copper iodide nanoparticles on poly(4-vinylpyridine): A new and efficient catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions
  作者：JALAL ALBADI、MOSADEGH KESHAVARZ、MASOUMEH ABEDINI、MOLOUD KHOSHAKHLAGH

  DOI：10.1007/s12039-013-0368-z

  日期：2013.3

  Poly(4-vinylpyridine)-supported nanoparticles of copper(I) iodide is reported as a new, efficient and recyclable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst can be recovered by simple filtration and recycled up to 10 consecutive runs without losing of its efficiency.

  报道了聚(4-乙烯基吡啶)负载的碘化亚铜纳米粒子作为一种新型、高效和可循环使用的催化剂，用于无溶剂条件下合成1,8-二氧代八氢氧杂蒽。该催化剂可以通过简单过滤回收，并且可以连续循环使用10次而不损失其催化效率。
• One-pot green and efficient synthesis of xanthenedione derivativesusing [C4 (mim) 2](FeCl4)2as a magnetic room temperature dicationic ionic liquid
  作者：Bijan Mombaini-Goodajdar、Ali Reza、Ali Ezabadi

  DOI：10.13005/ojc/310158

  日期：2015.3.28

  An easily prepared Fe (ΙΙΙ)-derived Lewis acid ionic liquid, [C4 (mim) 2] (FeCl4)2, being comprised of dicationic ionic liquid cation and tetrachloroferrate anion, was found to be an efficient, recyclable catalyst for the synthesis of 1, 8-dioxooctahydroxanthenes by one-pot condensation reactions of dimedone/ 1, 3- cyclohexanedione with aromatic aldehydes under mild reaction conditions without utilization of additional organic solvent

  一种易于制备的 Fe (ΙΙΙ) 衍生路易斯酸离子液体 [C4 (mim) 2] (FeCl4)2，由二阳离子液体阳离子和四氯化铁阴离子组成、8-dioxooctahydroxanthenes 的高效、可循环催化剂，该催化剂是在温和的反应条件下，通过二酮/1, 3- 环己二酮与芳香醛的一锅缩合反应合成的，无需使用额外的有机溶剂
• Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions
  作者：Simin Nazari、Mosadegh Keshavarz、Bahador Karami、Nasir Iravani、Masoumeh Vafaee-Nezhad

  DOI：10.1016/j.cclet.2013.12.011

  日期：2014.2

  Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions and recycled up to 8 consecutive runs without any losing of its efficiency. (C) 2013 Mosadegh Keshavarz. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.