12-phenyl-12H-benzo[a]xanthene | 116567-90-9

• 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-phenyl-12H-benzo[a]xanthene
• CAS: 116567-90-9
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: DHRFJHRQWCBROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2-hydroxynaphth-1-yl)-diphenylmethanol 以 溶剂黄146 为溶剂， 以30%的产率得到12-phenyl-12H-benzo[a]xanthene
  参考文献：
  名称：

  Solid-state dehydration of (o-hydroxyaryl)diphenylmethanols. Crystal and molecular structures of [1-(2-hydroxyphenyl)]diphenylmethanol and of [1-(2-hydroxynaphthyl)]diphenylmethanol

  摘要：

  DOI：

  10.1021/ja00534a016

文献信息

• A New Synthetic Route to Unsymmetrical 9-Arylxanthenes
  作者：Sajal Kumar Das、Ritesh Singh、Gautam Panda

  DOI：10.1002/ejoc.200900676

  日期：2009.10

  A facile and general three-step synthetic route towards unsymmetrical 9-arylxanthenes was developed. The reaction sequence involves nucleophilic substitution of commercially available 2-fluorobenzaldehydes with arenoxides, Grignard reaction of the resulting 2-arenoxybenzaldehydes with arylmagnesium bromides, followed by FeCl3-catalyzed intramolecular diarylmethylation of the resulting carbinols. This

  开发了一种针对不对称 9-芳基呫吨的简便通用的三步合成路线。反应顺序包括用芳氧化物对市售的 2-氟苯甲醛进行亲核取代，所得 2-芳氧基苯甲醛与芳基溴化镁的格氏反应，然后是 FeCl3 催化所得甲醇的分子内二芳基甲基化。该策略扩展到获得对称和不对称的 9-芳基噻吨。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• Microwave assisted benzylation of naphthols and 4-hydroxycoumarin under catalyst & solvent free conditions
  作者：Ravikrishna Dada、Garima Singh、Abhishek Pareek、Saeen Kausar、Srinivasarao Yaragorla

  DOI：10.1016/j.tetlet.2016.07.010

  日期：2016.8

  An expeditious and highly practical, microwave assisted benzylation of naphthols and 4-hydroxycoumarin has been developed under catalyst-free & solvent-free conditions. Alcohols undergo heat induced dehydration to form ethers, which collapse reversibly to form the carbocation which was captured immediately by a suitable nucleophile to furnish the benzylated compounds.

  在无催化剂和无溶剂的条件下，开发了一种快速且高度实用的萘酚和4-羟基香豆素的微波辅助苄基化方法。醇经历热诱导的脱水以形成醚，醚可逆地塌陷以形成碳阳离子，该碳阳离子被合适的亲核试剂立即捕获以提供苄基化的化合物。
• A green synthesis of unsymmetrical 9-arylxanthenes in a one-pot cascade benzylation/annulation/dehydration strategy
  作者：Srinivasarao Yaragorla、Pyare L. Saini、P. Vijaya Babu、Abdulrahman I. Almansour、Natarajan Arumugam

  DOI：10.1016/j.tetlet.2016.04.016

  日期：2016.6

  A green synthesis of unsymmetrical 9-arylxanthenones is described using Ca(OTf)2 in one-pot cascade benzylation, annulation and dehydration strategy starting from readily accessible π-activated carbinols. 4-Hydroxycoumarin/cyclohexane-1,3-dione required to be refluxed in water with 2-(hydroxy(phenyl)methyl)phenol derivatives in the presence of 5 mol % of Ca(OTf)2 to yield the unsymmetrical 9H-xanthenes

  使用Ca（OTf）2从容易获得的π-活化甲醇开始的一锅级联苄化，环化和脱水策略中描述了不对称9-芳基黄酮的绿色合成。需要在5摩尔％的Ca（OTf）2存在下，将4-羟基香豆素/环己烷-1,3-二酮与2-（羟基（苯基）甲基）苯酚衍生物在水中回流，以生成不对称的9H-黄嘌呤，而α/β-萘酚在无溶剂微波辐射条件下反应。使用环保的碱土金属催化剂，水作为溶剂，mw辐照，底物范围和高收率使该方法更加适用。
• 245. Reactions with benzoxanthones
  作者：Ahmed Mustafa、Mustafa Kamal Hilmy

  DOI：10.1039/jr9520001343

  日期：——
• Gomberg; McGill, Journal of the American Chemical Society, 1925, vol. 47, p. 2400
  作者：Gomberg、McGill

  DOI：——

  日期：——