2-氟蒽醌 | 572-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2-氟蒽醌
• 英文名称: 2-fluoroanthraquinone
• 英文别名: 2-fluoroanthracene-9,10-dione；2-fluoro-anthraquinone；2-Fluor-anthrachinon；β-Fluor-9,10-Anthrachinon；β-fluoro-anthraquinone；β-Fluoro-anthrachinon
• CAS: 572-84-9
• 化学式: C₁₄H₇FO₂
• mdl: MFCD00474514
• 分子量: 226.207
• InChiKey: LFZBKGLFBCHVMF-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  397.2±31.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟蒽醌 在 sodium nitrate 、 硫酸 作用下， 生成 1-Nitro-6-fluor-anthrachinon
  参考文献：
  名称：

  THE PREPARATION OF SOME FLUORO-NITRO-ANTHRAQUINONES AND THEIR REDUCTION TO AMINO-FLUORO-ANTHRAQUINONES

  摘要：

  不可用

  DOI：

  10.1139/v63-459
• 作为产物：
  描述：

  2-(4-氟苯酰基)苯甲酸 在 硫酸 作用下， 生成 2-氟蒽醌
  参考文献：
  名称：

  Hahn; Reid, Journal of the American Chemical Society, 1924, vol. 46, p. 1647

  摘要：

  DOI：

文献信息

• Extended Bis(anthraoxa)quinodimethanes with Nine and Ten Consecutively Fused Six-Membered Rings: Neutral Diradicaloids and Charged Diradical Dianions/Dications
  作者：Shaoqiang Dong、Tullimilli Y. Gopalakrishna、Yi Han、Hoa Phan、Tao Tao、Yong Ni、Gang Liu、Chunyan Chi

  DOI：10.1021/jacs.8b10279

  日期：2019.1.9

  respective nonacene and decacene. The dication ABA2+ and dianion ABA2- are open-shell singlet diradicaloids, while the longer dication ANA-TFA2+ and dianion ANA2- have closed-shell ground state, which can be explained by the different intramolecular Coulomb interactions. Both dianions have a bent backbone and can be considered as an isoelectronic structure of the tetraanion of nonacene and decacene, respectively

  我们报告了具有九个 (ABA) 和十个 (ANA) 连续稠合六元环的两种非常长的双（炭疽）醌二甲烷的具有挑战性的合成。前者稳定，双自由基特征可忽略不计，而后者具有中等双自由基特征 (y0 = 25.0%) 是反应性的，并且分离出意想不到的三氟乙酸取代产物 (ANA-TFA)。X 射线晶体学分析揭示了一个平面骨架，两者都具有典型的醌型特征。它们的指示可以被认为是相应的九苯和十苯的等电子结构。双离子 ABA2+ 和二价阴离子 ABA2- 是开壳单线态双自由基，而较长的双离子 ANA-TFA2+ 和二价阴离子 ANA2- 具有闭壳基态，这可以用不同的分子内库仑相互作用来解释。
• Stable Simple Enols. Resolution of Chiral 1-[9‘-(2‘-Fluoroanthryl)]-2,2-Dimesitylethenol. A Different Racemization Mechanism for the Enol and its Acetate¹
  作者：Elimelech Rochlin、Zvi Rappoport

  DOI：10.1021/jo020497q

  日期：2003.1.1

  expected for a rotational betabeta'-2-ring flip process in a vinyl propeller and the racemization is unaffected by added TFA, Et3N, and EtOD. Although 3 racemizes almost 350 times faster, the racemization is catalyzed by TFA and shows bell-shape catalysis by Et3N and a KIE in a partially deuteriated solvent. From this and the DNMR data, it is concluded that 3 does not racemize via a rotational betabeta'-2-ring

  手性1- [9'-（2'-甲氧基蒽基）]-2,2-二甲基间苯三酚（2），1- [9'-（2'-氟蒽基）]-2,2-二甲基间苯三酚（3）和1-合成了[9'-（2'-氟蒽基）]-2,2-二聚乙烯乙酸乙烯酯（4），研究了它们在C6D5NO2中的DNMR行为。将3和4在直链淀粉三（3，5-二甲基苯基氨基甲酸酯）HPLC柱上拆分为它们的对映异构体。醋酸盐4在DeltaG（e）（++），DeltaH（e）（++）和DeltaS（e）（++）值分别为26.2、27.6 kcal mol（-）（1）和4.3的溶液中缓慢消旋分别对乙烯基螺旋桨中的旋转betabeta'-2-环翻转过程而言是预期的eu，外消旋化不受添加的TFA，Et3N和EtOD的影响。尽管3的消旋速度快了350倍，但消旋作用由TFA催化，在部分氘代的溶剂中由Et3N和KIE呈钟形催化。从该数据和DNMR数据得出的结论是3不会​​通过旋转的betabeta'-2-ring
• Products of the condensation reaction of 2-(4-fluorobenzoyl)benzoic acid with m-cresol
  作者：J. Gronowska、A. Kalinowska

  DOI：10.1016/s0022-1139(00)80107-4

  日期：1993.4

  The preparation and structural elucidation of the new isomeric 3-(4-fluorophenyl)-3-(hydroxymethyl)phthalidesmade from m-cresol and 2-(4-fluorobenzoyl)benzoic acid aredescribed.

  制备和来自新的同分异构体3-（4-氟苯基）-3-（羟甲基）phthalidesmade的结构解析米甲酚和2-（4-氟苯甲酰基）苯甲酸aredescribed。
• Aromatic compounds containing fluorine and a process of preparing them
  申请人：HOECHST AG

  公开号：US02891074A1

  公开（公告）日：1959-06-16

  A process for the manufacture of aromatic compounds containing fluorine comprises reacting an aromatic compound containing one or more chlorine atoms bound to the nucleus and, in addition to chlorine, at least two strongly electro-negative substituents, at least one of which is, in the case of compounds of the benzene or naphthalene series, in ortho- or para - position (for naphthalene compounds "ortho-" includes 1 : 8-position and "para-" includes 2 : 5 position) to a chlorine atom, with dry potassium fluoride at a raised temperature and in absence of a solvent. The electro-negative substituents may be nitro, sulphonamido, sulpho-ester, carboxy-ester, carbamido, carboxyanhydride or trifluoromethyl groups or quinone oxygen (in the case of anthraquinones the chlorine atom or atoms may be in either the a - or b -positions). The process may be carried out by heating in a closed vessel to a temperature between 175 DEG and 275 DEG C., using appropriate quantities of potassium fluoride to partially or wholly replace chlorine atoms by fluorine atoms. New compounds prepared by the process are dinitro-chloro-difluorobenzenes from 1 : 3-dinitro-2 : 5 : 6-trichlorobenzene and from 1 : 3 - dinitro - 2 : 4 : 6 - trichlorobenzene; 1 : 3 - dinitro - 4 - fluoro - 5 - trifluoromethylbenzene from 1 : 3 - dinitro - 4 - chloro - 5 - trifluoromethyl - benzene; 2 - chloro - 3 - fluoronaphthoquinone from 2 : 3-dichloro-naphthoquinone; 1 - fluoroanthraquinone from 1-chloroanthraquinone; 1 : 8 - difluoroanthraquinone from 1 : 8 - dichloroanthraquinone; 2 : 5 - difluoro - 3 : 6 - dichloro - 1 : 4 - benzoquinone and 2 - fluoro - 3 : 5 : 6 - trichloro-1 : 4 - benzoquinon from chloranil; and 1-fluoro - 2 - nitrobenzene - 4 - sulphonic acid diethylamide from 1 - chloro - 2 - nitrobenzene-4 - sulphonic acid diethylamide. Other compounds which may be prepared by the process include 1 : 3 - dinitro - 4 : 6 - difluorobenzene and 1 : 3 - dinitro - 4 - chloro - 6 - fluorobenzene from 1 : 3 - dinitro - 4 : 6 - dichlorobenzene; 3-nitro - 4 - fluoro - benzoic acid - ethyl ester from 3 - nitro - 4 - chloro - benzoic acid ethyl ester; 3 - nitro - 6 - fluoro - benzoic acid methyl ester from 3-nitro-6-chloro-benzoic acid methyl ester; 4-fluoro-phthalic anhydride from 4-chloro-phthalic anhydride; and 2-fluoroanthraquinone from 2-chloroanthraquinone.

  一种制备含氟芳香化合物的方法包括将一种含有一个或多个氯原子结合到核上的芳香化合物与氟化钾在升高的温度下反应，且除氯外，还至少有两个强电负取代基，其中至少一个在苯或萘系列化合物中位于邻位或对位（对于萘化合物，“邻-”包括1:8位，“对-”包括2:5位）至氯原子。这些电负取代基可以是硝基、磺胺基、磺酸酯、羧酯、氨基、羧酸酐或三氟甲基基团或醌氧（在蒽醌的情况下，氯原子可以位于a-或b-位置）。该过程可通过在封闭容器中加热至175摄氏度至275摄氏度的温度，使用适量的氟化钾部分或完全用氟原子取代氯原子来进行。该过程制备的新化合物包括1:3-二硝基-氯二氟苯、1:3-二硝基-4-氟-5-三氟甲基苯、2-氯-3-氟萘醌、1-氟蒽醌、1:8-二氟蒽醌、2:5-二氟-3:6-二氯-1:4-苯醌、2-氟-3:5:6-三氯-1:4-苯醌、1-氟-2-硝基苯-4-磺酸二乙酰胺等。其他可能通过该方法制备的化合物包括1:3-二硝基-4:6-二氟苯、1:3-二硝基-4-氯-6-氟苯、3-硝基-4-氟苯甲酸乙酯、3-硝基-6-氟苯甲酸甲酯、4-氟邻苯二酐、2-氟蒽醌等。
• Access to Diarylmethanols by Wittig Rearrangement of <i>ortho-</i>, <i>meta-</i>, and <i>para-</i>Benzyloxy-<i>N</i>-Butylbenzamides
  作者：R. Alan Aitken、Andrew D. Harper、Ryan A. Inwood、Alexandra M. Z. Slawin

  DOI：10.1021/acs.joc.1c03160

  日期：2022.4.1

  promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric

  已发现N-丁基酰胺基团 CONHBu 是芳基苄基醚的 [1,2]-Wittig 重排的有效促进剂，因此允许从简单的羟基苯甲酸衍生物开始两步合成异构纯的取代的二芳基甲醇. 该方法与包括甲基、甲氧基和氟在内的多种官能团兼容，但不适用于硝基，而且出乎意料的是，该方法适用于间位以及邻位和对位异构体系列。

表征谱图