85960-75-4Relevant academic research and scientific papers
Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2 H-Chromenes
Song, Liyan,Su, Qian,Lin, Xi,Du, Zhihui,Xu, Huiyou,Ouyang, Ming-An,Yao, Hongliang,Tong, Rongbiao
, p. 3004 - 3009 (2020/04/20)
A new cascade approach has been developed for the one-pot four-step divergent synthesis of polysubstituted benzofurans and 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/Meinwald rearrangement/dehydrative or oxidative cyclization. This new method was demonstrated with 39 examples tolerating different substitutions at an epoxide, allylic ether, and aromatic ring, and we showcased its utility with the first total synthesis of natural product liparacid A in seven steps.
Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist
Nakamura, Tsuyoshi,Asano, Masayoshi,Sekiguchi, Yukiko,Mizuno, Yumiko,Tamaki, Kazuhiko,Kimura, Takako,Nara, Futoshi,Kawase, Yumi,Shimozato, Takaichi,Doi, Hiromi,Kagari, Takashi,Tomisato, Wataru,Inoue, Ryotaku,Nagasaki, Miyuki,Yuita, Hiroshi,Oguchi-Oshima, Keiko,Kaneko, Reina,Watanabe, Nobuaki,Abe, Yasuyuki,Nishi, Takahide
scheme or table, p. 1788 - 1792 (2012/04/04)
S1P3-sparing S1P1 agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P1 and over 5000-fold selectivity against S1P3. The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID 50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P1 and S1P3 showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P3, not in the case of Leu276 in S1P1. This observation gives an explanation for the excellent S1P3-sparing characteristic of CS-2100.
Palladium catalyzed isomerization of alkenes: A pronounced influence of an o-phenol hydroxyl group
Fan, Jinmin,Wan, Changfeng,Wang, Qiang,Gao, Linfeng,Zheng, Xiaoqi,Wang, Zhiyong
supporting information; experimental part, p. 3168 - 3172 (2011/02/25)
A novel palladium catalyzed isomerization of alkenes has been found, where an ortho-phenol hydroxyl group has a pronounced influence on the isomerization.
Palladium(II)-catalyzed enantioselective aerobic dialkoxylation of 2-propenyl phenols: A pronounced effect of copper additives on enantioselectivity
Zhang, Yang,Sigman, Matthew S.
, p. 3076 - 3077 (2008/04/18)
A direct O2-coupled Pd(II)-catalyzed enantioselective dialkoxylation of 2-propenylphenols has been developed by utilizing chiral quinoline oxazoline ligands. A detrimental effect of added copper salts on enantioselectivity was observed which is attributed to the displacement of the chiral ligand off of Pd(II). Copyright
Reaction of gem-dibromocyclopropanes or iodobenzofuran with trialkylmanganate
Kakiya, Hirotada,Inoue, Rie,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 2131 - 2137 (2007/10/03)
Treatment of gem-dibromocyclopropanes with trialkylmanganate, derived from manganese(II) chloride and three equivalents of Grignard reagent or alkyllithium, followed by an addition of electrophiles provided dialkylated cyclopropanes in good yields. It was
REACTION DE WITTIG EN MILIEU HETEROGENE SOLIDE-LIQUIDE : TRANSFORMATION DIRECTE DES ALDEHYDES PHENOLIQUES NATURELS EN ALCENES
Bigot, Yves Le,Delmas, Michel,Gaset, Antoine
, p. 193 - 196 (2007/10/02)
New alkenylphenols can be obtained directly, without protecting the phenol group from the condensation reaction between phenolic aldehydes and various phosphonium salts in the presence of potassium carbonate in protic and aprotic media, using a solid-liquid phase transfer.
The Behaviour of 2H-1-Benzopyrans Toward Trialkylaluminium Reagents
Alberola, Angel,Ortega, Alfonso Gonzalez,Pedrosa, Rafael,Bragado, Jose L. Perez,Amo, Justo F. Rodriguez
, p. 1209 - 1212 (2007/10/02)
2H-1-Benzopyrans react with trialkylaluminium compounds by alkyl- and hydrogen-transfer to C-2 and C-4 to give the o-allylphenols (2), (3), and the (E)-o-propenylphenols (4) and (5).The site of attack and the ratio of alkyl- to hydrogen-transfer depend on the alkylaluminium used and on the size of the substituent at C-2 of the pyran.A mechanism involving reaction of the alkylaluminium with the quinone methanide (6), which is in equilibrium with the pyran (1), is in accord with all experimental results.
