10,10-dimethyl-7-(thiophen-2-yl)-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one | 1224601-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 10,10-dimethyl-7-(thiophen-2-yl)-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one
• 英文别名: 10,11-dihydro-10,10-dimethyl-7-(thiophen-2-yl)-7H-benzo[c]xanthen-8(9H)-one；10,10-dimethyl-7-thiophen-2-yl-9,11-dihydro-7H-naphtho[1,2-b]chromen-8-one
• CAS: 1224601-88-0
• 化学式: C₂₃H₂₀O₂S
• 分子量: 360.477
• InChiKey: OPRNUQCFWUGWLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 萘酚 、 5,5-二甲基-1,3-环己二酮 在 L-proline triflate 作用下， 以 水 为溶剂， 反应 9.0h， 以70%的产率得到10,10-dimethyl-7-(thiophen-2-yl)-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one
  参考文献：
  名称：

  脯氨酸三氟甲磺酸酯催化水中苯并氧杂蒽合成的新策略

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2010.02.149

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。
• A multicomponent, solvent-free, one-pot synthesis of benzoxanthenones catalyzed by HY zeolite: their anti-microbial and cell imaging studies
  作者：Velladurai Rama、Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2011.10.143

  日期：2012.2

  An atom-economical, multicomponent condensation of naphthols, aldehydes, and cyclic 1,3-dicarbonyl compounds catalyzed by HY zeolites under solvent-free conditions is reported. This ecofriendly protocol offers several advantages such as a green and cost-effective procedure with excellent yield, shorter reaction time, simpler work-up, recovery, and reusability of metal-free solid acid heterogeneous catalyst and tolerance of a wide range of functional groups. The biological studies such as in vitro anti-microbial activities of the prepared new compounds and cell imaging studies on K562 leukemia cell lines by selected benzoxanthenones are evaluated. (C) 2011 Elsevier Ltd. All rights reserved.
• Preparation and characterization of Lewis acid grafted sulfonated carbon@titania composites for the multicomponent synthesis of 4H-pyrimido[2,1-b]benzothiazoles and benzoxanthenones under solvent-free conditions
  作者：Manmeet Kour、Satya Paul、James H. Clark、Vivek K. Gupta、Rajni Kant

  DOI：10.1016/j.molcata.2015.11.001

  日期：2016.1

  A series of novel and highly efficient Lewis acids covalently grafted over sulfonic acid functionalized carbon@titania composites were successfully synthesized via sulfonation of carbon@titania composites followed by treatment with different Lewis acids like AlCl3, FeCl3, SbCl3, SnCl2, Cu(OAc)(2) and Bi(NO3)(3), The utility of the developed catalysts was explored for the synthesis of a diverse range of 4H-pyrimido[2,1-b]benzothiazoles and benzoxanthenones, and among various catalysts, C/TiO2-SO3-SbCl2 was found to be the most active. We report here the synthesis of five novel compounds and the structure of one of the compounds has also been confirmed by single-crystal X-ray diffraction. All the five prepared composites were characterized by FTIR and ICP-AES analysis, whereas the most active one, C/TiO2-SO3-SbCl2 was further characterized by XRD, EDX, CHNS, SEM, TEM, HRTEM and TGA. The catalyst can be recovered and reused for atleast five runs without any significant impact on catalytic activity and selectivity. The high catalytic activity, thermal stability, simple recovery and reusability, and eco-friendly nature of the catalyst makes the present method to be particularly attractive from the view point of green chemistry. (C) 2015 Elsevier B.V. All rights reserved.