SU784195A1 - Process for producing 2-oleoylcyclohexane-1,3-dione - Google Patents

Process for producing 2-oleoylcyclohexane-1,3-dione Download PDF

Info

Publication number
SU784195A1
SU784195A1 SU792802224A SU2802224A SU784195A1 SU 784195 A1 SU784195 A1 SU 784195A1 SU 792802224 A SU792802224 A SU 792802224A SU 2802224 A SU2802224 A SU 2802224A SU 784195 A1 SU784195 A1 SU 784195A1
Authority
SU
USSR - Soviet Union
Prior art keywords
dione
oleoylcyclohexane
producing
chem
synthesis
Prior art date
Application number
SU792802224A
Other languages
Russian (ru)
Inventor
А.А. Ахрем
Ф.А. Лахвич
И.И. Петрусевич
Original Assignee
Институт Биорганической Химии Ан Бсср
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Институт Биорганической Химии Ан Бсср filed Critical Институт Биорганической Химии Ан Бсср
Priority to SU792802224A priority Critical patent/SU784195A1/en
Application granted granted Critical
Publication of SU784195A1 publication Critical patent/SU784195A1/en

Links

Landscapes

  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

получают njTeM изомеризации 3-олеоилокси-2-циклогексен-1-она формулы get njTeM isomerization of 3-oleoyloxy-2-cyclohexen-1-one of the formula

уat

аbut

О -с - tCH2)2 -CH OH-lCHz)7- СНзO-c - tCH2) 2 -CH OH-lCHz) 7-CH3

В присутствии ацетата натри  в расплаве при 160-170° С в инертной атмосфере.In the presence of sodium acetate in the melt at 160-170 ° C in an inert atmosphere.

Целевой продукт реакции выдел ют известными методами с выходом 66%. Строение 2-олеоилциклагексан-1,3-диона подтверждено его физико-химическими данными и сравнением их с описанными характеристиками природного продукта, а также других 2-ацилциклогексан-1,3-дионов 3,The desired reaction product was isolated by known methods with a yield of 66%. The structure of 2-oleoyl cyclahexane-1,3-dione is confirmed by its physicochemical data and their comparison with the described characteristics of the natural product, as well as other 2-acylcyclohexane-1,3-diones 3,

Пример. Смесь 1,2 г (3,2 мМоль) 3-олеоилокси-2-циклогексен-1-она и 0,27 г (3,3 ммоль) безводного плавленного ацетата натри  нагревают до образовани  однородной жидкой массы при 160-170° С в 30 мин в инертной атмосфере. Полученный Тёмнокрасный плав после охлаждени  раствор ют в 150 мл эфира и раствор дважды промывают водой (по 50 мл) и сушат сульфатом магни . Остаток после удалени  растворител  подвергают хроматографическому разделению на колонке с .силикагелем марки Л 40/100 |i. При элюировании системой эфир-гексан 1 :2 полу-чают 0,8 г (66%) 2-олевилциклогексан-1,3диона в виде бесцветного масла (кристал лизуетс  при хранении в холодильнике, т. пл. 10° С).Example. A mixture of 1.2 g (3.2 mM) of 3-oleoyloxy-2-cyclohexen-1-one and 0.27 g (3.3 mmol) of anhydrous fused sodium acetate is heated to form a homogeneous slurry at 160-170 ° C. 30 min in an inert atmosphere. The obtained dark red melt after cooling is dissolved in 150 ml of ether and the solution is washed twice with water (50 ml each time) and dried with magnesium sulfate. The residue after removal of the solvent is subjected to chromatographic separation on a column with silica gel brand L 40/100 | i. When elution with a 1: 2 ether-hexane system, 0.8 g (66%) of 2-olevylcyclohexane-1,3-dione is obtained as a colorless oil (crystallized during storage in a refrigerator, mp. 10 ° C).

ИК-спектр, V см-: 1665 (ел.), 1705 (с.) (CCU).IR spectrum, V cm-: 1665 (el.), 1705 (sec.) (CCU).

.----ИМР-снектр (5 ecu, м. д.): 0,91 (т., СНз - бок. цепи) 2,36 (т., -СН2-СОбок , цепи), 5,22 т. Н винильн., бок, цели), 18,18 (ОН енольн.)..---- IMR-spectrum (5 ecu, ppm): 0.91 (t., CH3 - side. Chains) 2.36 (t., -CH2-Sbok, chains), 5.22 t . N vinyl., Side, goals), 18,18 (OH enol.).

Найдено, %; С 76,42; Н 10,51. С,4Н4оОз, Вычислено, %: С 76,55; Н 10,71. Даннь1Й. способ получени  биологическиFound,%; C 76.42; H 10.51. C, 4Н4ООз, Calculated,%: C 76.55; H 10.71. Danny method of obtaining biologically

активного природного 2-олеоилциклогексан1 ,3-диона  вл етс  препаративным, основанthe active natural 2-oleoylcyclohexane1, 3-dione is preparative, based

на доступных исходных и HiveeT  вныеon available source and HiveeT explicit

преимущества перед способом . выделени advantages over the way. excreta

из природных источников.from natural sources.

Claims (3)

1. А. Mudd, . «Novel p-Triketones frorrt Lipidoptera, J. Chem. Soc. Chem. Commun., 1978, p. 1075. 1. A. Mudd,. “Novel p-Triketones frorrt Lipidoptera, J. Chem. Soc. Chem. Commun., 1978, p. 1075. 2.Авторское свидетельство СССР № 662543, кл. С 07 С 49/60, 1978.2. USSR author's certificate number 662543, cl. C 07 C 49/60, 1978. 3.А. А. Akhrem., и др. «А new Simple Synthesis of 2-Acylcyclohexane-l,3-diones, Synthesis, 1978, p. 925.3.A. A. Akhrem., Et al., “A New Simple Synthesis of 2-Acylcyclohexane-l, 3-diones, Synthesis, 1978, p. 925.
SU792802224A 1979-07-25 1979-07-25 Process for producing 2-oleoylcyclohexane-1,3-dione SU784195A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU792802224A SU784195A1 (en) 1979-07-25 1979-07-25 Process for producing 2-oleoylcyclohexane-1,3-dione

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU792802224A SU784195A1 (en) 1979-07-25 1979-07-25 Process for producing 2-oleoylcyclohexane-1,3-dione

Publications (1)

Publication Number Publication Date
SU784195A1 true SU784195A1 (en) 1982-01-23

Family

ID=20843219

Family Applications (1)

Application Number Title Priority Date Filing Date
SU792802224A SU784195A1 (en) 1979-07-25 1979-07-25 Process for producing 2-oleoylcyclohexane-1,3-dione

Country Status (1)

Country Link
SU (1) SU784195A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4695673A (en) * 1985-11-20 1987-09-22 Stauffer Chemical Company Process for the production of acylated 1,3-dicarbonyl compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4695673A (en) * 1985-11-20 1987-09-22 Stauffer Chemical Company Process for the production of acylated 1,3-dicarbonyl compounds

Similar Documents

Publication Publication Date Title
Johnson et al. Synthesis and characterization of prostacyclin, 6-ketoprostaglandin F1. alpha., prostaglandin I1, and prostaglandin I3
Ziegler et al. Cyclization of Chiral Carbon-Centered Aziridinyl Radicals: A New Route to Azirino [2', 3': 3, 4] pyrrolo [1, 2-a] indoles
DE2821403C2 (en) Decahydronaphthalene-1-spiro-2'-dihydrobenzofurans, processes for their preparation and pharmaceutical compositions containing these compounds
JPS61238757A (en) Manufacture of (+)s-2-hydroxy-2-methyl-hexanoic acid
Buechi et al. Structures of rubratoxins A and B
US3432541A (en) 9,15-dihydroxyprost-13-enoic acid and ester and preparation thereof
Hoare et al. Improved synthesis of racemic chorismic acid. Claisen rearrangement of 4-epi-chorismic acid and dimethyl 4-epi-chorismate
Hudlicky et al. Stereoselective Dimerizations of Arene-cis-diol Acetonides Derived from the Oxidation of Halobenzenes by Pseudomonas putida: Absolute Configuration of the Adducts by X-ray Crystallography
SU784195A1 (en) Process for producing 2-oleoylcyclohexane-1,3-dione
Flaming et al. β-Silylcarbonyl compounds as masked enones
DE2318852A1 (en) 7-ACYLAMIDO-3-HALOGEN-3-METHYL-CEPHAM4-CARBONIC ACID COMPOUNDS, PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
US2576104A (en) Dehydration and isomerization of straight-chain-conjugated polyene esters and acids
Avignon-Tropis et al. Total synthesis of (+)-leukotriene B4 methyl ester and its 5-epimer from (R)-glycidol
Toshimitsu et al. Carbon–carbon bond formation in diolefins using the new reagent ‘benzeneselenenyl iodide’
Ogura et al. A NEW TRANSFORMATION OF AN ESTER INTO ITS HOMOLOG AND AN α-HYDROXYALDEHYDE USING METHYL METHYLTHIOMETHYL SULFOXIDE
Ohno et al. Mg-Promoted Reductive Cross-Coupling of Ethyl. beta.-Arylacrylates with Aldehydes
Suzuki et al. A mild and efficient debromination of vicinal dibromoalkanes with sodium telluride prepared from tellurium and rongalite.
Brown et al. A stereospecific synthesis of trisubstituted alkenes via hydridation of dialkylhaloboranes followed by hydroboration-iodination of internal alkynes
Sih et al. Synthesis of (5E)-and (5Z)-11-deoxy-6, 11. alpha.-epoxy-. DELTA. 5-prostaglandin F1. alpha. sodium salts: 6, 11. alpha.-enol ether isomers of prostacyclin
US4379935A (en) Process for the synthesis of vincamine and related indole alkaloids
Sauers et al. New synthesis of 2-exo-brendanol
US3113970A (en) Process for preparing benzophenone compounds
SU555079A1 (en) The method of obtaining cyclopropylacetylene
JP3171400B2 (en) Hydroxycarbonyl derivative and method for producing the same
Koser et al. Nucleophilic methanolysis of 1-acetyltetracyclo [3.2. 0.02, 7.04, 6] heptane (2-acetylquadricyclene) and methyl 1-tetracyclo [3.2. 0.02, 7.04, 6] heptanecarboxylate (2-carbomethyoxyquadricyclene)