13-(4-methylphenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one | 1258870-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 13-(4-methylphenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one
• 英文别名: 12-(4-Methylphenyl)-2-oxapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1(13),3(11),4,6,8,14,16,18,20-nonaen-10-one
• CAS: 1258870-73-3
• 化学式: C₂₇H₁₈O₂
• 分子量: 374.439
• InChiKey: QQZPEIBAQPGJFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 对甲基苯甲醛 、 2-萘酚 在 三乙胺硫酸盐 作用下， 反应 0.2h， 以90%的产率得到13-(4-methylphenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one
  参考文献：
  名称：

  酸性离子液体催化12-芳基-12 H-茚并[ 1,2- b ]萘并[3,2 - e ]吡喃-5,11,13-三酮和13-芳基茚并[3，]的三组分合成， 2- b ]石脑[1,2 - e ]吡喃-12（13 H）-一衍生物

  摘要：

  通过2-羟基萘-1,4-二酮的三组分反应合成12-芳基-12 H-茚并[1,2- b ]萘并[3,2 - e ]吡喃-5,11,13-三酮衍生物，醛和2 H-茚-1,3-二酮在无溶剂条件下于70°C，在催化量的酸性离子液体如硫酸三乙铵（[Et 3 NH] [HSO 4 ]），三乙胺的存在下键合磺酸（[Et 3 N–SO 3 H] Cl），2-吡咯烷硫酸氢盐（[Hnhp] [HSO 4 ]），3-甲基-1-磺酸咪唑鎓氯化物（[Msim] Cl）和1 -甲基咪唑硫酸氢盐（[Hmim] [HSO 4]）。另外，由β-萘酚，醛与2 H-茚-1的反应生成的13-芳基茚并[1,2- b ]石脑[1,2 - e ]吡喃-12（13 H）-一衍生物据报道，在上述催化剂存在下，在无热溶剂的条件下，1-3-二酮。

  DOI：

  10.1016/j.molliq.2012.05.018

文献信息

• Phosphoric acid supported on alumina (H3PO4/Al2O3) as an efficient and reusable catalyst for the one-pot synthesis of benzoxanthene pigments
  作者：Hamid Reza Shaterian、Kobra Azizi、Nafiseh Fahimi

  DOI：10.1007/s11164-013-1047-x

  日期：2014.4

  Phosphoric acid supported on alumina (H3PO4/Al2O3) is an efficient catalyst for the catalytic multi-component condensation reaction and a wide variety of syntheses of benzoxanthene pigments in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction, and simple experimental and work-up procedures.

  负载于氧化铝上的磷酸（H3PO4/Al2O3）是一种高效的催化剂，可用于催化多组分缩合反应及一系列在良好产率下合成苯并二氧杂蒽类色素的合成中。该新方法的显著特点包括高转化率、较短的反应时间、更纯净的反应过程及简单易行的实验和后处理步骤。
• A rapid and quantitative synthesis of xanthene derivatives using sulfonated graphitic carbon nitride under ball‐milling
  作者：Omid Hosseinchi Qareaghaj、Mohammad Ghaffarzadeh、Najmedin Azizi

  DOI：10.1002/jhet.4327

  日期：2021.10

  A truly green, solventless, and fast protocol for the quantitative preparation of biologically active xanthene derivatives with 10 mol% sulfonated graphitic carbon nitride (Sg─CN) as a heterogeneous acidic catalyst was developed. Excellent yields, low cost, solvent-free conditions, high catalytic activity, reusability of the catalyst, simple workup, and heterogeneous carbon-based catalyst make the

  开发了一种真正绿色、无溶剂且快速的方案，用于定量制备具有 10 mol% 磺化石墨氮化碳 (Sg─CN) 作为多相酸性催化剂的生物活性呫吨衍生物。优异的收率、低成本、无溶剂条件、高催化活性、催化剂的可重复使用性、简单的后处理和非均相碳基催化剂使本方法从绿色化学的角度特别有吸引力。
• N-Sulfonic acid poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst for one-pot synthesis of xanthene derivatives in dry media under ultrasound irradiation
  作者：Nader Ghaffari Khaligh、Farhad Shirini

  DOI：10.1016/j.ultsonch.2014.06.020

  日期：2015.1

  N-Sulfonic acid poly(4-vinylpyridinium) hydrogen sulfate catalyzed efficiently the synthesis of xanthene derivatives under ultrasonic irradiation at room temperature, which has prompted various concerns involving cost and environmental persistence. This methodology shows the effect of presence of anion hydrogen sulfate as an important and effective factor on the promotion of the one-pot multi-components and condensation reactions. The catalyst can be recovered by simple filtration and used for several times without a significant loss of catalytic activity. (C) 2014 Elsevier B.V. All rights reserved.
• Silica Chloride Catalysed One-pot Synthesis of 13-Aryl-indeno[1,2-<i>b</i>]naphtha[1,2-e]pyran-12(13<i>H</i>)-ones under Solvent-free Conditions
  作者：Li-Qiang Wu、Li-Min Yang、Xiao Wang、Fu-Lin Yan

  DOI：10.1002/jccs.201000102

  日期：2010.8

  AbstractA simple and facile synthesis of 13‐aryl‐indeno[1,2‐b]naphtha[1,2‐e]pyran‐12(13H)‐ones has been accomplished by the one‐pot condensation of β‐naphthol, aldehydes, and 2H‐indene‐1,3‐dione under solvent‐free conditions in the presence of the heterogeneous catalyst silica chloride.
• Sulfamic acid-catalyzed synthesis of 13-aryl-indeno[1,2-b]-naphtha[1,2-e]pyran-12(13H)-ones under solvent-free conditions
  作者：Li Qiang Wu、Wei Lin Li、Fu Lin Yan

  DOI：10.1002/jhet.445

  日期：——

  Abstract magnified image The reaction of β‐naphthol with arylaldehydes and 2H‐indene‐1,3‐dione in the presence of sulfamic acid (3 mol %) under solvent‐free conditions led to 13‐aryl‐indeno[1,2‐b]naphtho[1,2‐e]pyran‐12(13H)‐ones in good yields. J. Heterocyclic Chem., (2010).