Alkaloids of the Australian Rutaceae: Acronychia baueri. II. Some Reactions of the Alkaloid Acronycine

1949 ◽  
Vol 2 (4) ◽  
pp. 622 ◽  
Author(s):  
RD Brown ◽  
LJ Drummond ◽  
FN Lahey ◽  
WC Thomas
Keyword(s):  
Double Bond ◽  
Methyl Ether ◽  
Weak Base ◽  
Alcoholic Potash ◽  
Hydroxyisobutyric Acid

Acronycine, C20H19O3N, is readily converted to noracroaycine, C19H17O3N, a weak base which contains no methoxyl. Acronycine contains a reactive double bond, shown to be present in a dimethylpyran ring by oxidation to an acid which, on heating, yields α-hydroxyisobutyric acid together with a phenol, Cl4H11O3N, and its methyl ether, Cl5H1303N. The action of alcoholic potash on acronycine results in the formation of two phenols, both of which are readily reconverted to acronycine. The bromination of acronycine has also been studied.

Hydrogenation of cinnamyl methyl ether and allylbenzene on palladium catalysts

1987 ◽  
Vol 52 (4) ◽  
pp. 1015-1020 ◽  
Author(s):  
Libor Červený ◽  
Ivo Paseka ◽  
Eva Fialová ◽  
Vlastimil Růžička
Keyword(s):  
Double Bond ◽  
Solvent Effect ◽  
Benzene Ring ◽  
Methyl Ether ◽  
Atmospheric Pressure ◽  
Palladium Catalysts ◽  
Polar Medium ◽  
Adsorbed Molecules ◽  
Ionic Nature ◽  
Bond Splitting

The hydrogenation of cinnamyl methyl ether and allylbenzene in hexane and acetone at 20 °C and atmospheric pressure of hydrogen has been studied on eight palladium catalysts. The hydrogenation of cinnamyl methyl ether is accompanied by C-O bond splitting giving rise to propylbenzene and methanol, the hydrogenation of allylbenzene is associated with the isomerization of the double bond resulting in its conjugation with the benzene ring. A marked solvent effect on the selectivity of hydrogenation of cinnamyl methyl ether has been observed and ascribed to the effect of solvated protons on the adsorbed molecules of the ether which is promoted by polar medium. The solvent effect on the isomerization of allylbenzene during the hydrogenation is little pronounced, which suggests that this reaction is not of ionic nature.

Synthesis of some 2,3- and 5,6-unsaturated 19-homosteroids bearing an oxygen containing group at the position 19a

1983 ◽  
Vol 48 (12) ◽  
pp. 3589-3596 ◽  
Author(s):  
Pavel Kočovský
Keyword(s):  
Double Bond ◽  
Methyl Ether ◽  
Hydroxyl Group ◽  
Key Steps

A synthesis of 5,6- and 2,3-unsaturated 19a-methoxy-19a-homocholestane derivatives XVII and XXI is reported. The key steps in the synthesis of the former compound is protecting the 3β-hydroxyl group and 5,6-double bond by conversion to a cyclosteroid (IX → VI, selective hydroboration of the protected steroid followed by methylation (VI → X → XI) and reductive removal of the 3β-substituent (XVI → XVII). The 2,3-unsaturated methyl ether XXI was obtained by elimination from the mesylate XX prepared from the 5,6-unsaturated derivative XV in three steps.

Chemistry of the Podocarpaceae. XXXV. 12-Methoxypodocarpa-8,11,13- triene and 12-Methoxyabieta-8,11,13-triene derivatives: A synthesis of (+)-hinokione methyl ether

1971 ◽  
Vol 24 (12) ◽  
pp. 2611 ◽  
Author(s):  
RC Cambie ◽  
TJ Fullerton
Keyword(s):  
Double Bond ◽  
Methyl Ether ◽  
Oxidative Decarboxylation ◽  
Reductive Methylation ◽  
Double Bond Isomerization ◽  
Epoxide Opening

12-Methoxypodocarpa-8,11,13-trien-19-oic acid (9) and 12-methoxyabieta- 8,11,13-trien-19-oic acid (10) have been converted into 3-0x0-4,4-dimethyl derivatives (15) and (18) by successive reactions involving oxidative decarboxylation, selective epoxidation, epoxide opening, double bond isomerization, oxidation, and reductive methylation. The sequence starting from the acid (10) provides a synthesis of the methyl ether of hinokione (14).

A test of the effects of pregnenolone methyl ether on subjective feelings of B-29 crews after a twelve-hour mission.

1955 ◽  
Author(s):  
Saul B. Sells ◽  
John R. Barry ◽  
David K. Trites ◽  
Herman I. Chinn
Keyword(s):  
Methyl Ether

Observations on a Relationship between Steroid Metabolism and the Concentration of Plasma Fibrinogen

1963 ◽  
Vol 10 (02) ◽  
pp. 400-405 ◽  
Author(s):  
B. A Amundson ◽  
L. O Pilgeram
Keyword(s):  
Blood Coagulation ◽  
Methyl Ether ◽  
Broad Spectrum ◽  
Human Subjects ◽  
Plasma Fibrinogen ◽  
Steroid Metabolism ◽  
Specific Site ◽  
Chain Reaction ◽  
Normal Human ◽  
A Chain

SummaryEnovid (5 mg norethynodrel and 0.075 mg ethynylestradiol-3-methyl ether) therapy in young normal human subjects causes an increase in plasma fibrinogen of 32.4% (P >C 0.001). Consideration of this effect together with other effects of Enovid on the activity of specific blood coagulatory factors suggests that the steroids are exerting their effect at a specific site of the blood coagulation and/or fibrinolytic system. The broad spectrum of changes which are induced by the steroids may be attributed to a combination of a chain reaction and feed-back control.

THE THYMOLYTIC ACTIVITY OF 6- AND 9-HALOCORTICOIDS AND RELATED STEROIDS

1965 ◽  
Vol 49 (2) ◽  
pp. 262-270 ◽  
Author(s):  
Ralph I. Dorfman ◽  
P. G. Holton ◽  
Fred A. Kind
Keyword(s):  
Double Bond ◽  
Subcutaneous Injection ◽  
Fluocinolone Acetonide ◽  
Relative Potency ◽  
Subcutaneous Route ◽  
Adrenalectomized Rats

ABSTRACT Adrenalectomized rats were used for the determination of the relative potency of various 6- and 9-halo substituted corticoids administered subcutaneously or by gavage using thymus weightas the endpoint. By subcutaneous injection, fluocinolone acetonide was the most active corticoid at 700 times that of cortisol. This compound was also the most active corticoid by the gavage route and was judged to be 570 times as active as the standard cortisol. The introduction of the 16,17-acetonide and 16,17-acetone 21-acetate groups into 17α,21-dihydroxy-9α,11β-dichloropregna-1,4-diene-3,20-dione increased the activity by a factor of 42 and 100, respectively. The introduction of the δ1 double bond into 6α-fluoroprogesterone 16,17-acetonide caused an increase of 10-fold in thymolytic activity assessed by the subcutaneous route

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