New, convenient route for trifluoromethylation of steroidal molecules

被引：27

作者：

Fei, XS ^{[1
]}

Tian, WS ^{[1
]}

Chen, QY ^{[1
]}

机构：

[1] Acad Sinica, Shanghai Inst Organ Chem, Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 06期

关键词：

D O I：

10.1039/a706552c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new convenient route for direct trifluoromethylation of steroidal compounds Is described. Steroidal alkenyl bromides, derived from steroidal unsaturated ketones, react with FO2SCF2CO2Me in the presence of CuI in DMF to give the corresponding trifluoromethylated steroids in good yields (70-91%).

引用

页码：1139 / 1142

页数：4

共 17 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[2] IMPROVED SYNTHESES OF EPRISTERIDE, A POTENT HUMAN 5-ALPHA-REDUCTASE INHIBITOR [J].

BAINE, NH ;

OWINGS, FF ;

KLINE, DN ;

RESNICK, T ;

PING, LJ ;

FOX, M ;

MEWSHAW, RE ;

TICKNER, AM ;

KOWALSKI, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5987-5989

[3] METHYL FLUOROSULFONYLDIFLUOROACETATE - A NEW TRIFLUOROMETHYLATING AGENT [J].

CHEN, QY ;

WU, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :705-706

[4] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .33. DIRECT TRIFLUOROMETHYLATION OF ARYL HALIDES WITH FLUOROSULPHONYLDIFLUOROMETHYL IODIDE IN THE PRESENCE OF COPPER - AN ELECTRON-TRANSFER INDUCED PROCESS [J].

CHEN, QY ;

WU, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2385-2387

[5]

CHEN QY, 1993, J CHEM SOC CHEM COMM, P1390

[6] STEROIDS .7. CONTRIBUTION TO THE BROMINATION OF DELTA-4-3-KETOSTEROIDS AND A NEW PARTIAL SYNTHESIS OF THE NATURAL ESTROGENS [J].

DJERASSI, C ;

ROSENKRANZ, G ;

ROMO, J ;

KAUFMANN, S ;

PATAKI, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4534-4540

[7] TRIFLUOROMETHYLATION OF ORGANIC HALIDES WITH METHYL HALODIFLUOROACETATES - A PROCESS VIA DIFLUOROCARBENE AND TRIFLUOROMETHIDE INTERMEDIATES [J].

DUAN, JX ;

SU, DB ;

CHEN, QY .

JOURNAL OF FLUORINE CHEMISTRY, 1993, 61 (03) :279-284

[8] MODIFIED STEROID HORMONES .1. SOME 4-BROMO-3-OXO-DELTA-4-DERIVATIVES [J].

KIRK, DN ;

PATEL, DK ;

PETROW, V .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (MAR) :627-629

[9] TRIFLUOROMETHYLATIONS AND RELATED REACTIONS IN ORGANIC-CHEMISTRY [J].

MCCLINTON, MA ;

MCCLINTON, DA .

TETRAHEDRON, 1992, 48 (32) :6555-6666

[10] THE 1ST CF3-SUBSTITUTED ORGANYL(CHLORO)SILANES [J].

RUPPERT, I ;

SCHLICH, K ;

VOLBACH, W .

TETRAHEDRON LETTERS, 1984, 25 (21) :2195-2198

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