12-ethyl-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one | 1011735-76-4

• 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: 12-ethyl-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
• 英文别名: 12-ethyl-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1011735-76-4
• 化学式: C₂₁H₂₂O₂
• 分子量: 306.404
• InChiKey: XFYVNUPFXRKSRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5,5-二甲基-1,3-环己二酮 、 丙醛 、 2-萘酚 在 sodium hydrogen sulfate 、 silica gel 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.8h， 以71%的产率得到12-ethyl-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
  参考文献：
  名称：

  一种用于合成新型 12-Aryl- 或 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one 衍生物的高效便捷方案

  摘要：

  已经描述了一种用于合成新型 12-芳基-或 12-烷基-8,9,10,12-四氢苯并[A]xanthen-11-one 衍生物的有效且直接的方法。该方法采用一锅三组分缩合反应，使用 2-萘酚、醛和环状 1,3-二羰基化合物，在催化量的 NaHSO 4 ·SiO 2 存在下，在 1,2-二氯乙烷中回流。

  DOI：

  10.1055/s-2007-990922

文献信息

• One-pot Green Procedure for Synthesis of Tetrahydrobenzo[a]xanthene-11-one Catalyzed by Brønsted Ionic Liquids under Solvent-free Conditions
  作者：Masoumeh Zakeri、Majid M. Heravi、Mina Saeedi、Narges Karimi、Hossein A. Oskooie、Niloofar Tavakoli-Hoseini

  DOI：10.1002/cjoc.201180240

  日期：2011.7

  An efficient one‐pot condensation of β‐naphthol, aldehydes and cyclic 1,3‐dicarbonyl compound has been achieved with ionic liquids as catalyst, thus a variety of 8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐one derivatives were prepared in good yields. The present approach offers several advantages such as shorter reaction times, good yields and mild reaction conditions.

  以离子液体为催化剂，可以实现β-萘酚，醛和环状1,3-二羰基化合物的高效一锅缩合，因此，各种8,9,10,12-四氢苯并[ a ]黄嘌呤-11-酮衍生物的制备得率很高。本方法具有几个优点，例如较短的反应时间，良好的产率和温和的反应条件。
• A facile and efficient method for synthesis of xanthone derivatives catalyzed by HBF4/SiO2 under solvent-free conditions
  作者：Zhan-Hui Zhang、Hong-Juan Wang、Xiao-Qian Ren、Yan-Yan Zhang

  DOI：10.1007/s00706-009-0204-9

  日期：2009.12

  was used as an efficient, green, and inexpensive catalytic system for synthesis of 12-aryl or 12-alkyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one derivatives via a one-pot three-component reaction of aldehydes, 2-naphthol, and cyclic 1,3-dicarbonyl compounds. The reactions proceeded rapidly at 80 °C under solvent-free conditions and the desired products were obtained in good to excellent yields.

  摘要HBF 4 / SiO 2被用作合成12-芳基或12-烷基-8,9,10,12-四氢-11 H-苯并[ a ]黄原-11-酮的高效，绿色且廉价的催化体系醛，2-萘酚和环状1,3-二羰基化合物的一锅三组分反应生成的衍生物。反应在无溶剂条件下于80°C迅速进行，并以良好至极好的收率获得了所需的产物。 图形概要
• Methanesulfonic Acid-Catalyzed One-Pot Synthesis of 12-Aryl or 12-Alkyl-8,9,10,12-tetrahydrobenzo[<i>a</i>]xanthen-11-one Derivatives
  作者：Yu-Heng Liu、Lei Li

  DOI：10.1002/jhet.882

  日期：2012.7

  An efficient synthesis of 12‐aryl or 12‐alkyl‐8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐one derivatives has been developed under solvent‐free conditions by one‐pot condensation of aldehydes, 2‐naphthol, and cyclic 1,3‐dicarbonyl compounds in the presence of a catalytic amount of methanesulfonic acid. The protocol has advantages of mild condition, short reaction time, high yield, and operational simplicity

  在无溶剂条件下，通过一锅法醛，2-萘酚，2-萘酚的缩合反应，已开发出有效合成12-芳基或12-烷基-8,9,10,12-四氢苯并[ a ]黄嘌呤-11-one衍生物的方法。和环状1,3-二羰基化合物在催化量的甲磺酸存在下 该方案具有条件温和，反应时间短，产率高和操作简单的优点。
• Diversity Oriented Synthesis of Benzoxanthene and Benzochromene Libraries via One-Pot, Three-Component Reactions and Their Anti-proliferative Activity
  作者：Atul Kumar、Siddharth Sharma、Ram Awatar Maurya、Jayant Sarkar

  DOI：10.1021/cc900143h

  日期：2010.1.11

  Libraries of benzoxanthenes, as well as of benzochromenes, were efficiently synthesized via one-pot, three-component reactions of 2-naphthol, aldehydes, and cyclic 1,3-diketones/malononitrile/ethyl cyanoacetate in the presence of catalytic amount of ceric ammonium nitrate (CAN) under solvent free conditions. The protocol offers rapid synthesis of structurally diverse benzoxanthenes and benzochromenes

  在催化量的铈铵存在下，通过2-萘酚，醛和环状1,3-二酮/丙二腈/氰基乙酸乙酯的一锅三组分反应，可以有效地合成苯并氧杂蒽和苯并色酮的库。无溶剂条件下的硝酸盐（CAN）。该协议可快速合成结构多样的苯并氧杂蒽和苯并二氢萘酮，以进行生物学筛选。评价所有合成的化合物的抗增殖活性，并且几种化合物表现出有希望的抗增殖活性。
• Efficient One-Pot Condensation of <font>β</font>-Naphthol, Aldehydes, and Cyclic 1,3-Dicarbonyl Compounds Catalyzed by <i>p</i>-TSA Under Solvent-Free and Sonication Conditions
  作者：Jianjun Li、Jia Li、Jin Fang、Weike Su

  DOI：10.1080/00397910903029966

  日期：2010.3.12

  A facile and efficient procedure has been developed by one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds for the synthesis of 8,9,10,12-tetrahydrobenzo[a]xanthen-11-one or 8,9-dihydrobenzo-[f]cyclopenta[b]chromen-10(11H)-one derivatives catalyzed by p-toluenesulfonic acid under solvent-free and sonication conditions.

  β-萘酚、醛和环状 1,3-二羰基化合物的一锅缩合已开发出一种简便有效的方法，用于合成 8,9,10,12-四氢苯并[a]xanthen-11-one 或在无溶剂和超声条件下由对甲苯磺酸催化的 8,9-二氢苯并-[f] 环戊二烯 [b] 色烯-10(11H)-one 衍生物。