42523-29-5Relevant articles and documents
Photodecaging from 9-substituted 2,7-dihydroxy and dimethoxyfluorenes: Competition between heterolytic and homolytic pathways
Roxin, Aron,Chase, Alex,Jeffers, Elizabeth,Lukeman, Matthew
, p. 920 - 930 (2011)
2,7-Dihydroxy-9-fluorenol (9), 2,7-dimethoxy-9-fluorenol (10), and 2,7-dimethoxy-9-acetoxyfluorene (11) were prepared and their photochemistry was studied in methanol and aqueous methanol solution in the hopes of observing efficient expulsion of the substituents positioned at the 9-position. For all three compounds, the primary photoproducts were 2,7-disubstituted-9-fluorenes and 2,7-disubstituted-9-methoxyfluorenes. A mechanism of reaction is proposed for production of these products, and involves competing homolytic and heterolytic pathways that produce radical and carbocation intermediates. Reaction quantum yields (for substrate disappearance) ranged between 0.21 and 0.31.
MANUFACTURING METHOD OF HYDROXYFLUORENONES
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Paragraph 0106-0108, (2019/06/21)
PROBLEM TO BE SOLVED: To provide a novel manufacturing method of hydroxyfluorenones. SOLUTION: By the method, a compound represented by the following formula (2) is manufactured by reacting a compound (A) represented by the following formula (1) and at least one kind of metal hydroxide (B) selected from alkali metal hydroxides, alkali earth metal hydroxides, and a hydrates thereof in presence of at least one kind of Periodic Table 11 group element-containing material (C) selected from simple substance of Periodic Table 11 group elements and compound containing the element, and a compound (D) having N,N'-substituted oxamide skeleton. Ar1 and Ar2 represent each independently an arylene ring, X represent each independently a halogen atom, R1 each independently represents a substituent, m1 and m2 represent integers of 0 or more, n1 and n2 represent integers of 0 or more and n1+n2 is 1 or more. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Palladium catalyzed domino C-H activation strategy: An access to 9- fluorenones
Patel, Anuj,Shaikh, Mahommedumar,Chikhalia, Kishor
supporting information, p. 236 - 245 (2018/12/11)
Palladium catalyzed domino C-H functionalization reaction of arylaldehyde with dihaloarene has been developed to access 9-flourenone molecules. Bidentate ligand assisted strategy, single step reaction, high yield and excellent functional group tolerance make this method concise and effective for the synthesis of 9-flourenone. In addition, proposed method has been successfully employed to synthesise Tilorone in gram scale.
Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group
Chen, Xiao-Yang,Ozturk, Seyma,Sorensen, Erik J.
, p. 1140 - 1143 (2017/03/14)
The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp2)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall yield (40%), demonstrating the utility of this method.
An effective synthesis method for tilorone dihydrochloride with obvious IFN-α inducing activity
Zhang, Junren,Yao, Qizheng,Liu, Zuliang,De Sousa, Maria Emília
, p. 21458 - 21463 (2016/01/25)
Tilorone dihydrochloride (1) has great potential for inducing interferon against pathogenic infection. In this paper, we describe a convenient preparation method for 2,7-dihydroxyfluoren-9-one (2), which is a usual pharmaceutical intermediate for preparing tilorone dihydrochloride (1). In the novel method, methyl esterification of 4,4′-dihydroxy-[1,1′-biphenyl]-2-carboxylic acid (4) was carried out under milder conditions with higher yield and played an important role in the preparation of compound 2. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS, and 1H-NMR. Furthermore, the synthesized tilorone dihydrochloride exhibited an obvious effect on induction of interferon-α (IFN-α) in mice within 12 h, and the peak level was observed until 24 h. This fruitful work has resulted in tilorone dihydrochloride becoming available in large-scale and wide application in clinics, which has a good pharmaceutical development prospects.
The influence of alkoxy chain length on the ferroelectric properties of chiral fluorenol liquid crystals
Roberts, Jeffrey C.,Hudson, Zachary M.,Lemieux, Robert P.
scheme or table, p. 3361 - 3365 (2010/01/09)
A series of isomeric chiral fluorenol mesogens with different alkoxy chain length combinations have been prepared in order to test a model for the origin of polar order in the chiral SmC* phase formed by these compounds. The results show that the transposition of alkoxy side chains has no effect on the sign of spontaneous polarization, PS, which is inconsistent with a model suggesting that polar order arises from a rotational bias of antiparallel hydrogen-bonded dimers that minimizes free volume in the tilted SmC* phase. The Royal Society of Chemistry 2008.
Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]- propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides
Epperson, James R.,Bruce, Marc A.,Catt, John D.,Deskus, Jeffrey A.,Hodges, Donald B.,Karageorge, George N.,Keavy, Daniel J.,Mahle, Cathy D.,Mattson, Ronald J.,Ortiz, Astrid A.,Parker, Michael F.,Takaki, Katherine S.,Watson, Brett T.,Yevich, Joseph P.
, p. 4601 - 4611 (2007/10/03)
Compound 2b demonstrated full agonism at both human MT1 and MT2 receptors and demonstrated chronobiotic activity in both acute and chronic rat models, producing an acute phase advance of 32 min at 1 mg/kg and chronically entraining free-running rats with a mean effective dose of 0.23 mg/kg. This compound was significantly less efficacious than melatonin in constricting human coronary artery. A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT 2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery.
3-ARYL- AND 3-(ARYLOXY)PHTHALIC ACIDS IN THE SYNTHESIS OF FLUORENONES AND XANTHONES
Oleinik, A. F.,Adamskaya, E. V.
, p. 1221 - 1224 (2007/10/02)
Aryl- and aryloxyfurans can serve as the starting compounds in the synthesis of fluorenones, xanthones, and diazafluoranthenes.
