12-(4-chlorophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1224601-84-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 12-(4-chlorophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 10,10-dimethyl-7-(4-chlorophenyl)-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one；7-(4-chlorophenyl)-10,10-dimethyl-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one；7-(4-chlorophenyl)-10,11-dihydro-10,10-dimethyl-7H-benzo[c]xanthen-8(9H)-one；7-(4-chlorophenyl)-10,10-dimethyl-9,11-dihydro-7H-naphtho[1,2-b]chromen-8-one
• CAS: 1224601-84-6
• 化学式: C₂₅H₂₁ClO₂
• 分子量: 388.894
• InChiKey: DCLJRMBXDZHGRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  萘酚 、 4-氯苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 pentafluorophenylammonium triflate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以97%的产率得到12-(4-chlorophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  五氟苯基三氟甲磺酸铵（PFPAT）：一种高效，实用且经济高效的催化剂，可用于一锅式缩合β-萘酚，醛和环状1,3-二羰基化合物。

  摘要：

  在轻度的反应条件下，五氟苯基三氟甲磺酸铵（PFPAT）催化剂（10 mol％）有效地促进了β-萘酚，醛和环状1,3-二羰基化合物的一锅缩合。从绿色化学的观点来看，这些催化缩合具有优点。PFPAT有机催化剂是空气稳定的，具有成本效益的，易于处理的，并且易于从反应混合物中除去。

  DOI：

  10.2174/138620712803901153

文献信息

• 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。
• Preparation and application of highly efficient and reusable TBAPIL@Si(CH2)3@nano-silica-based nano-catalyst for preparation of benzoxanthene derivatives
  作者：Akansha Agrwal、Vipin Kumar、Virendra Kasana

  DOI：10.1007/s13738-021-02211-1

  日期：2021.10

  were synthesized. Both of these were linked through propyltriethoxysilane to prepare a reusable catalyst TBAPIL@Si(CH2)3@silica NPs (TBAPILS). The formation of TBAPIL was checked through Fourier-transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) analysis. X-ray diffraction analysis confirmed the structure of silica NPs and linking of TBPAIL on it. Transmission electron microscopy

  制备脯氨酸四丁基铵离子液体（TBAPIL），合成介孔二氧化硅纳米粒子（NPs）。这两者通过丙基三乙氧基硅烷连接以制备可重复使用的催化剂TBAPIL@Si(CH 2 ) 3@silica NPs (TBAPILS)。通过傅里叶变换红外光谱 (FT-IR) 和核磁共振 (NMR) 分析检查 TBAPIL 的形成。X 射线衍射分析证实了二氧化硅 NPs 的结构和 TBPAIL 在其上的连接。透射电子显微镜证明了二氧化硅纳米粒子的蓬勃发展。扫描电子显微镜图揭示了二氧化硅 NPs 和 TBAPILS 的形态变化。FT-IR 分析也证实了 TBAPILS 催化剂的形成。此外，还检查了 TBAPILS 在合成四氢苯并氧杂蒽-11-酮的各种衍生物方面的有效性。所得化合物的形成和结构经FT-IR、元素分析、1 HNMR和13C NMR光谱分析。发现催化剂 TBAPILS 可以成功使用多达五个循环而没有显着的活性损失。
• Eco-friendly synthesis of tetrahydrobenzo[c]xanthenes catalyzed by functional ionic liquid in water
  作者：Jiaojiao Yang、Jinming Yang、Ting Zhu、Pingping Wang、Dong Fang

  DOI：10.1007/s00706-013-1057-9

  日期：2013.11

  AbstractA clean procedure for the synthesis of tetrahydrobenzo[c]xanthenes was established in the presence of a functional ionic liquid, 1-butyl-(4-dimethylamino)pyridinium hydroxide [BDMAP][OH]. The reaction was carried out via the one-pot multi-component condensation of aromatic aldehydes, cyclic 1,3-dicarbonyl compounds, and α-naphthol in aqueous media, to afford good to excellent yields ranging

  摘要在功能性离子液体1-丁基-（4-二甲基氨基）吡啶鎓氢氧化物[BDMAP] [OH]存在下，建立了合成四氢苯并[ c ]黄嘌呤的清洁方法。该反应是通过在水性介质中一锅法将芳族醛，环状1,3-二羰基化合物和α-萘酚进行多组分缩合来实现的，在60-90范围内，产率从80％到85％不等。分钟 反应后，催化剂可以循环使用几次，而催化活性没有明显降低。 图形概要
• Alum-Catalyzed Domino Synthesis of 12-Substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones Under Solvent-Free Conditions
  作者：Rajan Kumar Sharma、Rajni Khajuria、Kamal K. Kapoor

  DOI：10.1080/00397911.2014.935794

  日期：2014.12.17

  Alum is found to catalyze efficiently the one-pot, three-component condensation of aldehydes, alpha/beta-naphthol, and dimedone to afford various 12-substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones in excellent yields. The use of alum catalyst and the solvent-free conditions make this method simple, convenient, eco-friendly, and cost-effective.
• Thiamine hydrochloride as a promoter for the efficient and green synthesis of 12-aryl-8,9,10,12 tetrahydrobenzoxanthene-11-one derivatives in aqueous micellar medium
  作者：Shahin Fatma、Pravin K. Singh、Preyas Ankit、Shireen、Mandavi Singh、J. Singh

  DOI：10.1016/j.tetlet.2013.09.125

  日期：2013.12

  An environmentally benign, three-component, one-pot integrated chemical process has been developed for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzoxanthene-11-one by nucleophilic addition reaction between aldehyde and beta-naphthol followed by Michael addition of dimedone, catalyzed by thiamine hydrochloride in aqueous micellar medium with excellent yield. Simple reaction conditions, no requirement of chromatographic separation, short reaction time, ease of isolation, use of inexpensive, easily recoverable and reusable catalyst makes this protocol very interesting from an economic and environmental perspective. (C) 2013 Elsevier Ltd. All rights reserved.