The preparation and properties of 1,1-difluorocyclopropane derivatives

被引：40

作者：

Adekenova, Kymbat S. ^{[1
]}

Wyatt, Peter B. ^{[1
]}

Adekenov, Sergazy M. ^{[2
]}

机构：

[1] Queen Mary Univ London, Sch Biol & Chem Sci, Mile End Rd, London E1 4NS, England

[2] JSC Int Res & Prod Holding Phytochem, Karaganda 100009, Kazakhstan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷

关键词：

biological activity; cyclopropanation; difluorocyclopropane derivatives; synthesis; GEM-DIFLUOROCYCLOPROPYL KETONES; RING-OPENING REACTIONS; HALOMETHYL METAL-COMPOUNDS; EFFICIENT SYNTHESIS; THERMAL REARRANGEMENT; BUILDING-BLOCKS; DIFLUORINATED CYCLOPROPANES; METHYLENE DERIVATIVES; FLUORINE-COMPOUNDS; LIQUID-CRYSTALS;

D O I：

10.3762/bjoc.17.25

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recently, the functionalization of organic molecules with fluorine substituents has grown rapidly due to its applications in such fields as medicine, agriculture or materials sciences. The aim of this article is to review the importance of 1,1-difluorocyclopropane derivatives in synthesis. It will examine the role of the fluorine substituents in both ring-forming and ring-opening reactions, as well as methods for obtaining difluorocyclopropanes as single enantiomers. Several examples are provided to highlight the biological importance of this class of compounds.

引用

页码：245 / 272

页数：28

共 50 条

[1] EXPERIMENTAL-STUDY ON THE REACTIONS OF VIBRATIONALLY EXCITED 1,1-DIFLUOROCYCLOPROPANE
LAUTERWALD, H
HEYDTMANN, H
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1991, 23 (05) : 369 - 375
[2] MICROWAVE-SPECTRUM, STRUCTURE, AND DIPOLE-MOMENT OF 1,1-DIFLUOROCYCLOPROPANE
PERRETTA, AT
LAURIE, VW
JOURNAL OF CHEMICAL PHYSICS, 1975, 62 (06): : 2469 - 2473
[3] Scaled quantum chemical force fields for 1,1-difluorocyclopropane and the influence of vibrational anharmonicity
McKean, Donald C.
Craig, Norman C.
Law, Mark M.
JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (29): : 6760 - 6771
[4] AB-INITIO CALCULATIONS ON THE STEREOMUTATION OF 1,1-DIFLUOROCYCLOPROPANE - PREDICTION OF A SUBSTANTIAL PREFERENCE FOR COUPLED DISROTATION OF THE METHYLENE GROUPS
GETTY, SJ
HROVAT, DA
BORDEN, WT
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) : 1521 - 1527
[5] Design, Synthesis, and Biological Investigation of Epothilone B Analogues Featuring Lactone, Lactam, and Carbocyclic Macrocycles, Epoxide, Aziridine, and 1,1-Difluorocyclopropane and Other Fluorine Residues
Nicolaou, K. C.
Shelke, Yogesh G.
Dherange, Balu D.
Kempema, Aaron
Lin, Baiwei
Gu, Christine
Sandoval, Joseph
Hammond, Mikhail
Aujay, Monette
Gavrilyuk, Julia
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 2865 - 2917
[6] Preparation and properties of 1,1'-disubstituted trichotomine derivatives with a twisted C=C bond
Irikawa, H
Kanke, S
Mito, K
Kobayashi, Y
Akasaka, T
Atsumi, T
Arimoto, H
Okumura, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (06) : 1673 - 1677
[7] Preparation of novel difluorocyclopropane nucleosides
Csuk, R
Thiede, G
TETRAHEDRON, 1999, 55 (03) : 739 - 750
[8] Vibrational spectroscopy of 1,1-difluorocyclopropane-d0, -d2, and -d4:: The equilibrium structure of difluorocyclopropane
Craig, Norman C.
Feller, David
Groner, Peter
Hsin, Hong Yuan
McKean, Donald C.
Nemchick, Deacon J.
JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (13): : 2498 - 2506
[9] PREPARATION AND PROPERTIES OF COMPOUNDS WITH MIXED TRIVALENT STRUCTURE . DIMETHYLAMINO-1 GEMDIALCOXY-1,1 DERIVATIVES
FEUGEAS, C
OLSCHWAN.D
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1968, (12): : 4985 - &
[10] Preparation of Dihydroborole Derivatives by a Simple 1,1-Carboboration Route
Feldmann, Andreas
Iida, Azusa
Froehlich, Roland
Yamaguchi, Shigehiro
Kehr, Gerald
Erker, Gerhard
ORGANOMETALLICS, 2012, 31 (06) : 2445 - 2451

← 1 2 3 4 5 →