Synthesis of (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene - a trifluoromethyl analogue of necrodols

被引：5

作者：

Dmowski, W ^{[1
]}

Piasecka-Maciejewska, K ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 105卷 / 01期

关键词：

fluorination; sulphur tetrafluoride; fluoroterpenoids; fluoronecrodol; methyl (1S,3R,3S)-4-(trifluoromethyl)-2,2,3-trimethylcyclopentanecarboxylate; methyl (3S,4R)-3-(trifluoromethyl)-4,5,5-trimethylcyclopentenecarboxylate; (3S,4R)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene;

D O I：

10.1016/S0022-1139(00)00283-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New trifluoromethyl group containing enantiomerically pure monoterpene derivatives, methyl (1S,3R,4S)-(+)-3-(trifluoromethyl)-2,2,3-trimethylcyclopentanecarboxylate (6); methyl (3S,4R)-(+)-3-(trifluoromethyl)-4,5,5-trimethylcyclopentenecarboxylate (10) and (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene (1), were prepared using camphoric anhydride as the starting material and sulphur tetrafluoride as the fluorinating agent. Compound 1 is a trifluoromethyl analogue of an unknown isomer of necrodols. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：77 / 82

页数：6

共 15 条

[1] REACTION BETWEEN AROMATIC COMPOUNDS AND DERIVATIVES OF TERTIARY ACIDS .13. STRUCTURE OF PHENYLCAMPHORIC ACID [J].

BANTICK, JR ;

ROTHSTEI.E .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (14) :2512-&

[2] FORMATION AND STRUCTURE OF PHENYLCAMPHORIC ACID AND RELATED COMPOUNDS [J].

BIRD, CW ;

YEONG, YC .

TETRAHEDRON, 1974, 30 (02) :321-325

[3] REACTION BETWEEN AROMATIC COMPOUNDS AND DERIVATIVES OF TERTIARY ACIDS .12. FRIEDEL-CRAFTS REACTIONS OF CAMPHORIC ANHYDRIDE IN ANISOLE AND IN BENZENE [J].

BLEAZARD, W ;

ROTHSTEIN, E .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JAN) :68-&

[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[5] NATURE OF ORTHO EFFECT .2. COMPOSITION OF TAFT STERIC PARAMETERS [J].

CHARTON, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (03) :615-&

[6] Selective fluorination of (1S,4R)-(-)-camphanic acid with sulphur tetrafluoride:: preparation of new fluorinated optically active derivatives of camphor and 1,2,2-trimethylcyclopentane [J].

Dmowski, W ;

Piasecka-Maciejewska, K .

JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :97-100

[7] Selective fluorination of (1R,3S)-(+)-camphoric acid with sulphur tetrafluoride. Preparation of fluorinated optically active derivatives of 1,2,2-trimethylcyclopentane [J].

Dmowski, W ;

Kozlowski, T .

JOURNAL OF FLUORINE CHEMISTRY, 1997, 83 (02) :187-190

[8] Expedient synthesis of (1R,3S)-(+)-3-(trifluoromethyl) camphonanic acid and derivatives [J].

Dmowski, W ;

Piasecka-Maciejewska, K .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1999, 31 (02) :207-211

[9] Reactions of carboxyl derivatives of camphor with sulphur tetrafluoride [J].

Dmowski, W ;

Piasecka-Maciejewska, K .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 104 (02) :273-276

[10]

FILLER R, 1979, ORGANOFLUORINE COMPO, pCH6

← 1 2 →