SCIENTIFIC ABSTRACT MAKSIMOV, V.I. - MAKSIMOV, V.M.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001031630001-6
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Sequence Number: 1
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

Investigations in the Field of the Synthesis of 79-2-55/64
Steroid Hermone Analogs. 2
III. The Production of 3-(p-Methoxy Phenlvl)- A6 -Cyclo pentene-
1-on-2-Acetic Acid
Robinson aid Terner. The methyl ether obtained from the acid,
however, had its meltinF, point at 88-890C as already given in
technical literature. The acid quoted in the title was
synthesized also accordine to the method by Robinson, however,
also a melting point of 145-5 - 1460C was obtained. The
spectroscopic iivestigations of the acids obtained by both
methods with the melting point 145.5 - 1460C confirm the
acid quoted in the title. Apparently Robinson and Terner
obtained an ot,-ier polymiorphous modification melting at
17/30C. Detailed data of preparation are given.
There are 1 fiCure, and 6 references, 1 of which is Slavic.
ASSOCIATION: All-Union Ctiemicall-Pharmaceutical Scientific Research
Institute imeni S. Ordzhonikidze (Vsesoyuznyy nauchno-
issledovatellskiy khimiko-farmatsevticheskiy institut im.
S. Ordzhonikidze).
SUBMITTED: November 1, 1957
AVAILABLE: Library of ConCress
Card 2/2

AUTHORS: Grinenko, G. S., Maksimov, V. 1. 79-2-56/64
TITLE: Investigations in the Field of the Steroid Hormon(- Analocs
(Issledovaniya v oblasti analoeov .9teroidnykh I-ormonov).
IV. On the Catalytic Hydrogenation of the 3-(p-Me.hoxy
Phenyl)- 4 2 Cyclopentene-l-on-2-Acetic Acid 2
P. 0 kataliticheskom gidrirovanii 3-(p-metoksifenil)-
tsiklopenten-l-on-2-uksusnoy kisloty).
PERIODICAL: Zhurnal Obshchey Khimii, 1958, Vol. 28, Nr 2, pp. 532-538
(USSR)
ABSTRACT: In the ~.orks by Weidlich it was found (ref. 1) that on the
occasion of the prcduction of the u, 0-unsaturated ketones,
under the presence of a Pd-catalyst mainly transketone occurs
in the alcoholi:-- or neutral medium, while ci.,;-ketoz e
is produced in the acid medium. This aErees with the
observations made by Zallkind (ref. 2) and Otto (ref.
that on the occasion of fast hydrot:enation (in the Fizid
medium) the cis-i3omer with greater enerey occ~.-.rs wh~.le an
the occasion of the prolonEati--n of the rea2tiDn '.in the
alkaline medium) the trans isomer 17~th less ene-cy J3 formed
i -- L
to an increased extert. On the o3casion of hydro,,enation of
Card 1/3 the acid quoted in "he title trans-,'-/p-r-ethcxy phenyl)-

Investigations in the Field of the Steroid Hormone Ana'Lri;s 79-2-56/64
cyclopentane-l-on-2-acetic acid (I), lactones of the syn-
cis-3 (p-methoxy phonyl)-ryclopentane-l-or,-2-acetic acid (II)
and cis-2-(p-methoxy p~,~ioriyl)-cyclol)entane-l-acetic acid (III)
were obtained in alkaline or neutral medium while tht: latter
occurred only in acid medium. The verification of the cis-
confit;uration of (M) was carried out accordinp to a method
by Klemmen3 mod"fied ~y (zl~f- 4). The syn-cis-confi-
Luration of (I!) was by verified the reduotion of the carbonyl
f it - 'de -~asion t~ie
group 0 J) Tt4th Na-boror, hydr- -)r. which uc
reaction took Diace stereo-directed. On this oc,,asion 7~.6 ~o
of an anti-trans-oxy-acid (melting point 36-87`0 and 20 of
an ant_-*-ci3-oxy-a_-id was formed which was isolated as lactone
(:.,elting point 141-1420C). Since the first also after an
action of lonCer duration did not lactonize it proves the
anti-trans-confi,:uration oorresponding to the Alder-Stein
theorem (ref. 5). The results of hydroCenation obtained
correspond to the propositions made by Neidlich (ref. 1) and
Teilacker and Dr53sler (ref. 6). Hydrogen addition may take
place on the double bond C=C or C=O. Since hydroLenation in
the acid medium is possible only accordinC to the second
Card 2/3 method no saturated ketones can be obtained. The isolation

Investigations in the Field of the Steroid Hormone Analoes 79-2-56/64
of an alcohol intermediate product confirms the mechanism
of the catalytic hydrofenation of a, P-unsaturated ketones
mentioned before. Detailed data of preparation as well as
structural formulae are given.
There are 7 references, 1 of which is Slavic.
LSSOCIATION:AU-Union Chemical-Pharmaceutical Scientific Research
ins'~i~UL (Vsesoyuznyy nauchnoissledovateI-Iskly
khimiko-farmatsevti6heskiy ii1stitut)
SUBMITTED: November 1, 1957
AVAILABLE: Library of Congress
Card 3/3

AUT17'RS: Maksimov, V. I., Grinenko, G. S. S')7/7 9- 2 6-8-55/66
TITLE: Investigation of the Synthesiv of the Steroid Hormone Analogs
(Issledovaniye v oblasti sinteza analogov steroidnykh gormonov)
V.Synthesis of Some Compounds of the Cyclopentanetetrahydro-
naphthalene Series (V. Sintez nekotorykh soyedineniy tsiklo-
pentanotetragidronaftalinovogo ryada)
PERIODICAL: Zhurnal obshchey khimii, 1958, Vol. 28, Nr 8,
pp. 2179 - 2182 (USSR)
ABSTRACT: InvestiC;ating the syr~thesis of the analo.-s of the steroid
hormones the authors found tricyclic cpmpounds which contain
the rings B,C and D of the steroid nucleus. The cis- and trans-
-4-keto-6-met,lioxy-1,2-cyclopentane-1,2,3,4-tetrahydronaphtha-
lene, (II) and (IV), were formed at the intramolccular
acylation of the cis-and trans-isomers of the 2-(p-methoxy-
phenyl)-cyclope.itane-l-acetic acid (I,V) (Ref 1',. The
cyclization occLixei according to three methods: Under the
influence of the polyphosphoric acid, of hydrogen fluoride
and according to Friedel-Crafts (Fridel~-Krafts), using
Card 1/3 tin (II) chloride as condensing agent. In any case, the

Investigation of the Synthesis of the Steroid Hormone SOV/79-28-8-39/66
Analogs. V.Synthesis of Some Compounds of the Cyclopentanetetrahydro-
naphthalene Series
cis-acid (I) yielded nearly quantitatively the cis-tricyclic
ketone (II), the trans-acid (V), however, yielded 70% only
of the trans-tricyclic ketone. Compound (II) and its semi-
carbazone have low melting points and are more readily
soluble than the corresponding compounds of the trans-series.
This is in accord with the well-known fact, that a trans-isomer,
as a rule, melts at hig'ner temperature and is less soluble.
The various tendencies towards cyclization of the cis-- and
trans-acids (I), (V), the phys-,cal constants and solubilities
of the tricyclic compounds produced from these acids confi=.
the accuracy of the sugCested configuration (Ref 1). There
are 4 references, 1 of which is Soviet.
ASSOCIATION: Vsesoyuznyy nauchno-issiedovatellskiy khimiko-farmatsevticheskiy
institut imeni S.Ordzhonikidze (All-Union Scientific Chemical-
Pharmace,itical Research Institute ime' S. Ordzhonikidze)
Card 2/3

Investigation of the S.,-nthesis of the Steroid Hormone SOV/79-28 _8_7 9/66
A,nalogs. V. Synthesis of Some Compounds of the Cyclopentanetetrahydro-
naphthalane Series
SUBUTTED: June 28, 1957
Card 3/3

AUTHORS: Maksimov, V. I., Grimenko, G. S. SOV/79-28-8-4o/66
TITLE: Investigation in the Field of the Synthesis of the Steroid-
Hormone Analogs (Issledovaniya v oblasti sinteza analogov
steroidnykh gormonov) VI. Experiments on the Cyclization of
the Trans-3-(p-Methoxy-Phenyl)-Cyclopentane-l-One-2-Acetic
Acid and Its Derivatives (VI. Opyty po tsiklizatsii trans-3-
-(p-metoksifenil)-taiklopentan-l-on-2-uksusnoy kisloty i
yeye proizvodnykh)
PERIODICAL: Zhurnal obshchey khimii, 1956, Vcl. 28, Nr 8,
pp. 2182 - 2187 (USSR)
ABSTRACT: In order to obtain a trans-configuration of the rings in
the tricyclic ketone (Formula 17) at the cyclizatior of the
trans-keto acid (XVI), the carbonyl group of this acid
must be converted into another one which excludes the possi-
bility of an*pim~~rization cf the neighboring asymmetric
hydrocarbon atam. Par this reason a cyclization of the ethylene-
ketal of the trans-3-(p-methoxy phenyl)-cyclopentane-1-one-
-2~aaetic acid (X111), of the anti-trans-3-(p-methoxy phenyl)-
-qyc I open t ane- T-acetozy-2-aceti c acid (XVIII) was carried
Card 1/3 qut. The-athyleneketal af the trans-keto acid (XIII) was

Investigation In the Field of t1m ftn'thosis mff the la/79-28-8-4o/66
Steroid-Hormone, Analogs,. VI. Ex7ertments = the QyeZiZation. of the Trans-3-
-(p-Mothoxy-Phenyl)-Cyclopentane-T-4kTe-2-Acatio Acid an(t Its Derivatives
obtained accord-ing- to them methadl hy 'SUludo Anner, Miescher
(Tilando. Annerp Ulxhew-~ (~ftt s4ftae 5~)., Summarizing,
attempts were mad* t;o, pwforw ths (WaUWtot of the trans-3-
-.(p-methoxy acid, of the
athylene-ketal of' this wid and,-.of tht antl-trans-3-(P-me-
thoxy 6611 by means
of hydrogen fluori&&p w14 tad, socording
t~a the method- byy ftie&*I~~tfta, It was
seen that in all threw me ear th* oylfliz~"ion- of these com-
pounds which. hav& ta. jpa&tlaw T 9L flMot1oft&I otygen atom
occurs, undem fammaSiton. at W* mMevpA&rfg 14t4tones and not
of' the expected; tx_:I~apa=o~ ko~ew.- V&*M avr* I figures and
WE referencesp 1' af WHI& is Sdvi4t.-
ASSOCIATION.:. Vessoyuznyy naucfhno--i4illail~OvWtol:"sktyf khimi1