Elsevier’s Encyclopædia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds

873 Pages·1959·34.522 MB·English

by  F. Radt (auth.), F. Radt (eds.)

ELSEVIER'S ENCYCLOPJEDIA
of
ORGANIC CHEMISTRY
ELSEVIER'S
ENCYCLOP~DIA
of
ORGANIC CHEMISTRY
Series 111
CARBOISOCYCLIC CONDENSED COMPOUNDS
Volume 14-Supplement
Pages 2215 S-2990 S
STEROIDS
OXO-COMPOUNDS
Under the auspices of Beilstein-Institut für Literatur der Organischen Chemis
Edited by F. RADT
SPRINGER-VERLAG BERLIN HEIDELBERG GMBH 1959
In this volume the Literature has been consulted up to
and including 1946, the Literature concerning the structure and configuration
of compounds up to 1958
Die Wiedergabe von Gebrauchsnamen, Handelsnamen, Warenbezeichnungen usw.
im BeiJstefu.Handbuch berechtigt auch ohne besondere Kennzeichnung nicht zu
der Annahme, daß solche Namen im Sinn der Warenzeichen. und Markenschutz.
Gesetzgebung als frei zu betrachten wären und daher von jedermann benutzt
werden dürften.
ISBN 978-3-662-23761-8 ISBN 978-3-662-25863-7 (eBook)
DOI 10.1007/978-3-662-25863-7
Alle Rechte, insbesondere das der Übersetzung in fremde Sprachen, vorbehalten.
Ohne ausdrückliche.~ Genehmigung des Verlags ist es auch nicht gestattet,
dieses Buch oder Teile daraus auf fotomechanischem Wege
(Fotokopie, Mikrokopie) zu vervielfältigen.
© Springer-Verlag Berlin Heidelberg 1959
Ursprünglich erschienen bei Springer-Verlag Berlin • Göttingen • Heidelberg 1959
Softcoverreprint of the hardcover 1st edition 1959
PREFACE
When, a few years ago, the publication of Elsevier's Encyclo
pa:dia of Organic Chemistry was suspended, it seemed desirable
to complete-on account of its monographic character-the steroid
section in accordance with the original conception. One conside
ration in favour thereof, among others, was that the steroid section
of Beilstein's Handbuch will not be available for some years to
come, so that also to those using Beilstein the present publication
is a valuable help in bridging the gap. In view of the undiminished
activity in this special field- equally important to chemists, bio
chemists, and the medical world - the hope that the completion
of this section will meet the needs of a wide circle of readers ap
pears tobe justified.
Altogether three more volumes are planned for the Supplement,
the first of which, now presented, covers the steroid Oxo-com
pounds, the Iiterature having been consulted up to the end of
1946 in conformity with the previous volumes of the steroid
Supplement. Where, however, important additions and correc
tions are concerned, Iiterature up to the most recent date has been
taken into account. In treating the subject matter the same prin
ciples have been followed as in the previous volumes of this
section. Editorship remains in the competent hands of Dr. F.
RADT, who has contributed a considerable proportion of the matter
treated in this volume. He is assisted by Dr. A. GEORG and Dr.
DoRA STERN.
Frankfurt a. M., May, 1959 F. RICHTER
CONTENTS
Pages
Preface V
Table of Abbreviations XVII
Reproduction of Structural Formulre XIX
Table of Periodicals .. XXI
Steroids (continued) 22I5 s
OXO-COMPOUNDS 22I5 s
I. CO in Side Chain Only 2215 s
A. Mono-oxo-Compounds .. 2215 s
I. Compounds without another functional group 2215 s
e. g., Pregnan-20-one 2217 s
Norcholanyl methyl ketone 2218 s
2-Formylcholestene .. 22I9 s
2. Halogeno -monooxo -compounds 2221 s
a. Halogen in side chain only .. 2221 s
e. g., 2I-Chloropregnan-2o-one .. 2221 s
b. Halogen in the ring system 222I s
e. g., 3ß-Chloro-LI5-pregnen-20-one 2222 s
I 7.2 I -Dibromoallopregnan-20-one 2223 s
3· Diazo-monooxo-compounds 2224 s
e. g., 2I-Diazopregnan-20-one .. 2224 s
Norcholanyl diazomethyl ketone 2224 s
4· Hydroxy-monooxo-compounds .. 2225 s
a. OH in side chain only .. 2225 s
e. g., Pregnan-2I-ol-20-one 2225 s
Norcholanyl hydroxymethyl ketone 2226 s
b. OH (at least one group) in the ring system 2226 s
I. Morwhydroxy-ketones without other functional
groups .. 2226 s
et. Monohydroxy-ketones with two aliphatic
side chains .. 2226 s
VoL. 14 s CONTENTS VII
Pages
ß. Monohydroxy-ketones C with three ali
20
phatic side chains 2227 s
e. g., I7ß-Formylandrostan-31X-ol 2228 s
y. Monohydroxy-ketones C with three alipha
21
tic side chains 2229 s
e. g., Pregnen-3-ol-20-ones etc. (Summary) 2229 s
i-Pregnen-6ß-ol-20-one 225 I S
Allopregnan-3ß-ol-21 -al 2252 s
<5. Monohydroxy-ketones C and higher with
22
three aliphatic side chains 2258 s
e. g., 17ß-Acetonyl-LI5-androsten-3ß-ol 2258 s
N orallocholan-3ß-ol-22 -one 226I s
Allocholan-31X-ol-24-al 2262 s
27 -N orcholestan-31X-ol-2 5 -one 2264 s
2 2-Ketocholesterol 2265 s
s. Monohydroxy-ketones with four aliphatic
side chains .. 2267 s
e. g., 16-Methyl-LI5-pregnen-3ß-ol-2o-ones 2268 s
3-Acetylcholestan-3-ol 2270 s
~- Monohydroxy-ketones containing cyclic radi
cals in side chain 2271 s
e. g., 21-Benzyl-LI5-pregnen-3ß-ol-2o-one 2272 s
3ß-Hydroxy-LI5-pregnen-2o-yl phenyl
ketone .. 2273 s
31X-Hydroxynorcholanyl phenyl
ketone .. 2275 s
2. Halogeno-monohydroxy-ketones 2277 s
IX. Halogen in sidc chain only 2277 s
e. g., 21-Halogenopregnen-3-ol-20-ones etc.
(Summary) .. 2277 s
2 I--Chloromethyl-Ll5-pregnen-3ß-ol-
2I-one .. 2282 s
2 I .2 I -Dibromo-LI5-pregnen-3ß-ol-
20-one ..
ß. Halogen in the ring system ..
e. g., 17-Bromopregnan-3ß-ol-2o-one
r 7.2 I -Dibromo-LI5-pregnen-3ß-ol-
20-one ..
I 6. I 7 -Dibromopregnan-3ß-ol-2o-one
51X.6ß. I 7.2 I-Tetrabromo-allopregnan-
3ß-ol-20-one 2290 s
3. Amino-monohydroxy-ketones .. 2292 s
e. g., 2 I -Amino-LI5-pregnen-3ß-ol-2o-one 2292 s
VIII CONTENTS VoL. I4 s
Pages
4· Diazo-monohydroxy-ketones .. 2292 s
e. g., 2I-Diazo-L15-pregnen-3,8-ol-2o-one .. 2293 s
26-Diazo-L15-norcholesten-3.B-ol-25-one 2298 s
5· Dihydroxy-ketones with one OH in side chain,
the other in the ring system 2300 s
e. g., Pregnene-3.2I-diol-20-ones etc.
(Summary) .. 2300 s
L15-Pregnene-3,8.2o-diol-2I-al .. 2312 s
Cholane-3oc.24-diol-23-one 2315 s
6. Dihydroxy-ketones with both OH in the ring system 2320 s
e. g., I7,8-Formylandrostane-3,8.I7oc-diol 2321 s
Pregnanediol-20-ones etc. (Summary) 2322 s
Cholane-3oc.7oc-diol-23-one 2346 s
3oc. I 2oc-Dihydroxynorcholanyl phenyl
ketone .. 2350 s
7· Halogeno-dihydroxy-compounds (both OH in the
ring system) .. 2351 s
e. g., I 2oc-Bromopregnane-3oc. II,ß-diol-20-one 2351 s
8. Diazo-dihydroxy-compounds (both OH in the ring
system) .. 2352 s
2 I -Diazopregnane-3oc. I 2oc-diol-2o-one 2352 s
9· Trihydroxy-compounds containing two OH in the
ring system .. 2353 s
e. g., Dihydroxypregnan-21-ol-20-ones etc.
(Summary) .. 2353 s
24.24-Diethylcholane-3oc. 12oc. 24-triol-
23-one ..
ro. Trihydroxy-compounds with all OH in the ring
system ..
e. g., Pregnane-3oc.7oc.I2oc-triol-2o-one
II. Halogeno- and Diazo-trihydroxy-compounds (all
OH in the ring system) 2370 s
I2. Tetrahydroxy-compounds containing one OH in side
chain 2372 s
e. g., Allopregnane-3oc.II,B.I7.2I-tetrol-20·one 2373 s
B. Dioxo-Compounds
e. g., L15-Pregnen·3P·ol·20·on·2I·al ..
24-Phenylcholane-3oc. 7oc. I 2oc-triol-2 3· 24-dione
VoL. 14 s CONTENTS IX
II. Oxo-Compounds with CO in the Ring System ..
A. Mono-oxo-Compounds ..
I. Compounds without other functional groups 2383 s
I. Compounds without side chain 2383 s
e. g., 5'-Keto-1.2-cyclopentenophenanthrene .. 2384 s
2. Compounds with one aliphatic side chain 2387 s
e. g., Desoxyequilenin 2389 s
3· Compounds with two aliphatic side chains 2396 s
Androstanones etc. (Summary) 2396 s
4· Compounds C -C with three aliphatic side chains 2405 s
20 26
e. g., 17ß-Methylandrostan-3-one 2406 s
Pregnan-3-one .. 24II S
23 -Methylcholan-3 -one 2413 s
5· Compounds C with aliphatic side chains 2416 s
27
e. g., Cholestanones etc. (Summary) 2416 s
6. Compounds C with aliphatic side chains 2458 s
28
e. g., Ergostenones etc. (Summary) 2458 s
6oc-Methyl-L14-cholesten-3-one .. 2464 s
7· Compounds C with aliphatic side chains 2465 s
29
Ketones with sitostane skeleton (Summary) 2465 s
8. Compounds containing cyclic radicals in side chain 2472 s
e. g., 24.24-Diphenylcholatrien-3-one 2472 s
11. Halogeno-monoketo-steroids .. 2473 s
I. Halogeninside chain only 2473 s
e. g., 21-Bromopregnadien-3-one 2473 s
2. Monohalogeno-compounds (halogen in the ring system) 2474 s
a. Compounds C19-C21 2474 s
e. g., 3-Chloroandrostan-17-ones 2476 s
4ß-Bromopregnan-3-one .. 2477 s
b. Compounds C27-C29 2479 s
e. g., Monohalogeno-monoketones with cholestane
(or coprostane) skeleton (Summary) 2479 s
3ß -Chlorositostan -6-one 2490 s
3· Polyhalogeno-compounds (halogen in the ring system) .. 2493 s
e. g., 5.6-Dibromoandrostan-17-one 2493 s
Di- and Tri-halogenocholestanones (Summary) 2493 s
2.2.5oc.6ß-Tetrabromocholestan-3-one 2505 s
111. Nitro- and Amino-monoketo-steroids 2507 s
e. g., 20-Amino-Ll4-pregnen-3-one 2508 s
17-Amino-retiocholan-3-one 2509 s
X CONTENTS VoL. I4 s
Pages
IV. Hydroxy-monoketo-steroids .. 2510 S
I. OH in side chain only 2510 s
e. g., Pregnan-20oc-ol-3-one 25 I I s
Ll4-Pregnene-20.2 I -diol-3-one 25I4 s
2. Monohydroxy-compounds (OH in the ring system) C17 25 r6 s
e. g., I8-Nor-isoequilenin .. 25 rS s
3· Monohydroxy-compounds (OH in the ring system) with one
aliphatic side chain 2521 s
a. Methyl compounds with CH in other positions than
3
at C-I3 2521 s
c. g., 7-Methyl-4-hydroxy-3' -keto-1.2-cyclopenteno
phenanthrene 2521 s
b. Methyl compounds with CH at C-I3 2524 s
3
oc. CO in 3-, I2-, or I6-position 2524 s
e. g., CEstran-I7ß-ol-3-one 2524 s
ß. CO in I7·position 2525 s
e. g., Equilenin 2527 s
Equilin 2539 s
CEstrane 2543 s
Lumicestrone 2559 s
CEstran-3-ol-I 7-one 2562 s
c. Monoalkyl (except Methyl) compounds 2570 s
e. g., I8-Ethylequilenin 2571 s
4· Monohydroxy-compounds (OH in the ring system) with two
aliphatic side chains, not derived from androstane or
atiocholane .. 2573 s
e. g., I6-Methylequilenan-3-ol-I7-one 2573 s
5· Androstanolones etc. (Summary) 2575 s
e. g., Testosterone 2580 s
Dehydroepiandrosterone 2609 s
Androsterone 2629 s
Luminandrosterone .. 2640 s
6. Monohydroxy-compounds C -C with three aliphatic side
20 26
chains .. 2645 s
e. g., I7-Methyltestosterone 2645 s
I7-Ethynyltestosterone ("Pregneninolone") .. 2648 s
I7-Allyltestosterone .. 2653 s
Pregnen-3-ol-I I-ones 2654 s
N orcholan-3oc-ol-I 2 -one 2656 s
I 6-Isopropylidene-5 -dehydroepiandrosterone 2656 s
7· Monohydroxy-compounds C with three alipha#c side chains 2658 s
27
Cholestenolones etc. (Summary) 2658 s
8. Monohydroxy-compounds C with three aliphatic side chains 2690 s
28
Ergostadienolones etc. 2690 s