10-羟基-10-苯基-10H-菲-9-酮 | 102555-32-8

• 中文名称: 10-羟基-10-苯基-10H-菲-9-酮
• 英文名称: 10-hydroxy-10-phenylphenanthren-9(10H)-one
• 英文别名: 10-Hydroxy-10-phenylphenanthren-9-one
• CAS: 102555-32-8
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: XQBXFNFUTRFZCP-UHFFFAOYSA-N

物化性质

• 熔点：
  118-118.5 °C
• 沸点：
  505.4±49.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 10-羟基-10-苯基-10H-菲-9-酮
  参考文献：
  名称：

  Studies of Quinoid Structures. I. Action of Arylmagnesium Halides on Phenanthrenequinonimine

  摘要：

  DOI：

  10.1021/jo01359a006

文献信息

• Synthesis of new derivatives of a representative o-quinone scaffold by reduction at the electrode
  作者：Belen Batanero、Fructuoso Barba、Fernando Ranz、Isidoro Barba、Michail N. Elinson

  DOI：10.1016/j.tet.2012.05.042

  日期：2012.7

  concomitant electrochemical reduction of 9,10-phenanthrenequinone and benzenediazonium tetrafluoroborate, under constant potential conditions (−0.5 V vs Ag/Ag+), has been performed in different organic solvents. An interesting entry to new C–C radical coupling products is here described. Another cathodic pathway where the anion radical intermediate acts as an EGB is also described. The electrochemical behaviour

  在不同的有机溶剂中，在恒定电势条件下（-0.5 V对Ag / Ag +），进行了9,10-菲醌和四氟硼酸苯重氮的伴随电化学还原。这里介绍了一个新的C–C自由基偶联产品的有趣条目。还描述了其中阴离子自由基中间体充当EGB的另一种阴极途径。给出了系统的电化学行为和机理建议。
• Serendipitous discovery of Pd-catalyzed intramolecular cyclization of ortho-bromo(hetero)aryl-substituted (hetero)aryl-1,2-diketones: Applications in the synthesis of carba- and heterocyclic benzoin derivatives
  作者：Erich Ammon、Aleksandra Khomutetckaia、Alexander Villinger、Peter Ehlers、Peter Langer

  DOI：10.1016/j.tet.2023.133335

  日期：2023.4

  heterocyclic benzoin derivatives were prepared by Sonogashira coupling of alkynes with 1,2-dihaloalkenes and subsequent oxidation of the alkyne to a 1,2-diketone. The Pd-catalyzed reaction of the product with (2-bromophenyl)boronic acid in the presence of phenylacetylene resulted in formation of cyclic benzoin derivatives by Suzuki-Miyaura reaction and subsequent Pd catalyzed nucleophilic addition

  卡巴 和杂环安息香衍生物是通过 Sonogashira 将炔烃与 1,2-二卤代烯烃偶联，然后将炔烃氧化为 1,2-二酮制备的。在苯乙炔存在下，产物与 (2-溴苯基) 硼酸的 Pd 催化反应导致通过 Suzuki-Miyaura 反应形成环状安息香衍生物，随后 Pd 催化亲核加成到羰基。迄今前所未有的 5-hydroxy-5-phenylbenzo[ b ]naphtho[1,2- d ]thiophene-6(5H)-ones 及其区域异构体是从 2,3-二溴苯并噻吩制备的。以2-溴-1-碘苯为原料制备了菲安息香衍生物。
• Photoalkylation/-arylation of <i>ortho</i>-Diketones with Unactivated Organic Halides
  作者：Xiao-Yu Wang、Yong-Qin He、Yi Zhou、Lin Lu、Xian-Rong Song、Zhao-Zhao Zhou、Wan-Fa Tian、Qiang Xiao

  DOI：10.1021/acs.orglett.3c01191

  日期：2023.6.2

  A new method for conducting a reductive alkylation/arylation of 1,2-diketones using visible light and unactivated organic halides is presented in this article. This technique does not require a photocatalyst and employs Et3N, a tertiary amine, as a promoter. This amine aids in generating a ketyl radical and an α-aminoalkyl radical, which engages in a C–X bond activation via a halogen atom transfer

  本文介绍了一种使用可见光和未活化的有机卤化物对 1,2-二酮进行还原烷基化/芳基化的新方法。该技术不需要光催化剂，并使用叔胺Et 3 N 作为促进剂。这种胺有助于生成一个羰基自由基和一个 α-氨基烷基自由基，后者通过卤素原子转移过程 (XAT) 参与 C-X 键活化。这种方法的成功取决于利用 Et 3 N 作为启动子。本文温和直接的协议允许显着扩展有机卤化物底物，包括主要、次要和芳香族有机卤化物和各种官能团。
• Asymmetric catalysis. Part 153: Metal-catalysed enantioselective α-ketol rearrangement
  作者：Henri Brunner、Henri B. Kagan、Georg Kreutzer

  DOI：10.1016/s0957-4166(03)00433-6

  日期：2003.8

  Promoted by catalytic amounts of Ni complexes tertiary alpha-hydroxyketones 1a, 3a-5a undergo rearrangement, forming chiral isomers 1b, 3b-5b. The best enantioselection was obtained with the model system 1-benzoylcyclopentanol 4a/2-hydroxy-2-phenylcyclohexanone 4b. In a ligand screening 2-[4-(S)-tert-butyloxazolin-2-yl]pyridine gave the highest enantiomeric excess of 46% (S)-4b. The analogous isomerisation reactions of alpha-hydroxyimines 6a, 7a forming chiral alpha-aminoketones 6b, 7b were established. (C) 2003 Elsevier Ltd. All rights reserved.