SU677661A3 - Способ получени производных дибензо( )пиран-9(8н)-она - Google Patents

Способ получени производных дибензо( )пиран-9(8н)-она

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SU677661A3
SU677661A3 SU772506503A SU2506503A SU677661A3 SU 677661 A3 SU677661 A3 SU 677661A3 SU 772506503 A SU772506503 A SU 772506503A SU 2506503 A SU2506503 A SU 2506503A SU 677661 A3 SU677661 A3 SU 677661A3
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pyran
hydroxy
dimethyl
dibenzo
dihydro
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Синг Биндра Джасджит
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Пфайзер Инк. (Фирма)
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
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Description

В раствор 0,916 г 5-окси-З-оксиметилен2 ,2-диметил-7-(1 - метил-4-фенвлбутил)-4хроманона в 4 мл метанола и 0,037 мл метилвинилкетона добавл ют 0,09 мл триэтцламина . Реакционную смесь перемешивают в течение 16 ч при комнатной температуре и затем разбавл ют 50 мл серного эфира. Приготовленный диэтиловоэфирный раствор экстрагируют 4 порци ми по 50 мл 10%-ного раствора карбоната натри , сушат над сульфатом натри  и концентрируют в вакууме с получением 1,09 г маслоподобного продукта. Остаток кип т т с обратным холодильником вместе с 7,3 мл этанола и 7,3 мл 2 н. раствора гидрата окиси кали  в течение 16 ч. После этого реакционньщ раствор охлаждают, подкисл ют 6 н. раствором сол ной кислоты и экстрагируют 3 порци ми по 20 мл дихлорметана. Органическ )ао фазу сушат над сульфатом натри  и выпаривают с получением 0,99 г маслоподобного продукта, который кристаллизуют из смеси серного эфира с гексаном в соотношении 1 : 1, в результате чего получают 0,49 г rf/-6a, 7-дигидpo-l-oкcи-6,6-димeтил-3 (l-мeтил - 4-фенилбутил)-6Н-дибензо &,й( пиран-9-(8Н)-она; т. пл. 145-148°С (после кристаллизации из изопропилового эфира).
Результаты элементного анализа дл  СгеПзоОз, %:
Вычислено, %: С 79,97; Н 7,74.
Пайдено, %: С 79,91; Н 7,78.
Подобным же образом d/-6a, 7-дигидро-1окси-6 ,6-диметил - 3-(1-метил-5 - фенилпентил )-6Н-дибензо Ь, сг пиран-9(8Н)-он получают из 5-окси-3-оксиметилен-2,2-диметил-7 (1-метил-фенилпентил)-4-хроманона; т. пл. 204-208°С.
Результаты элементного анализа дл  дл  С27Нз2Оз, %:
Вычислено, %: С 80,16; Н 7,97.
Найдено, В: С 80,00; Н 8,29.
dl-6a,7 - Дигидро-1-окси-6,6-диметил-3-(2фенилэтил - 6Н-дибензо1 6, й пиран-9{8Н)он получают из 5-окси-3-оксиметилен-2,2-диметил-7- (2-фенилэтил)-4-хроманона; температура плавлени  составл ет 233-235°С.
d/-6a, 7-Дигидро - 1-окси-6,6-диметил-3-(1метил-3 - фенилпропил)-6Н - дибензб 6дй пиран-9(8Н)-он из 5-окси-З-оксиметилен2 ,2-диметил-7-(1-метил - 3-фенилпропил)-4хроманона; т. пл. 181°С.
dl-6a-a,-7 - Дигидро-1-окси-6а-метил-3-(1метил - 4-фенилбутил)-6Н - дибензо Ь,пиран-9 (8Н)-он получают из /-5-окси-3-оксиметилен-2 - метил - 7-(1 - метил-4-фенилбутил )-4-хроманона; т. пл. 195-197°С.
Результаты элементного анализа дл  СгбНгвОз, %:
Вычислено, %: С 79,75; Н 7,50.
Найдено, %: С 79,76; Н 8,33.
d/-6a, 7-Дигидро - 1-окси-6,6-диметил-3-(1метил-4 - феноксибутил)-6Н - дибензо 6,й пиран-9(8Н)-он получают из соответствуюшего 3-оксиметиленового производного; т. пл. 165-176°С.
Результаты элементного анализа дл  С2бНзо04, %:
Вычислено, %: С 76,82; Н 7,44. Найдено, %: С 76,80; Н 7,57. dl-Qa,7 - Дигидро-1-окси-6,6-диметил-3- 1метил-4- (4 - пиридил)-бутил -6Н - дибензо Ьх/ пиран-9(8Н)-он получают из соответствуюш ,его 3-оксиметиленового производного в форме стекловидного твердого продукта . Результаты элементного анализа дл 
C25H29N03-H20, %:
Вычислено, %: С 73,32; Н 7,62; N 3,42.
Найдено, %: С 73,22; Н 7,37; N 3,25.
/-6а,7-Дигидро - 1-окси-6,6-диметил-3- 1метил-2- (2-фенилэтокси)-этил -6Н - дибензо Ь ,й(пиран-9(8Н)-он получают из dl-2,2дикетил-3 - оксиметилен-5-окси-7- 1-метил2- (2-фенилэтокси)-этил -4-хроманона; т. пл. 185-187°С.
Пример 2. dl-6a, 7-Дигидро-1-окси-6,6диметил - 3-(2-гептилокси)-6Н-дибензо &,йг
пиран-9(8Н)-он.
В раствор 5,17 г (15,4 ммоль) с /-5-оксиЗ-оксиметилен-2 ,2 - диметил - 7-(2-гептилокси )-4-хроманона и 2,27 мл (27,9 ммоль) метилвинилкетона в 23 мл метанола добавл ют 0,54 мл трнэтиламина. Реакционную смесь перемешивают в течение 16 ч при комнатной температуре и затем разбавл ют 250 мл серного эфира. Конечный эфирный раствор экстрагируют 6 порци ми по
30 мл 10%-ного раствора карбоната натри , над сульфатом натри  и концентрируют в вакууме с получением 6,11 г маслоподобного продукта. Остаток кип т т с обратным холодильником совместно с 45 мл
этанола и 45 мл 2 н. раствора гидрата окиси калц  в течение 16 ч. После этого реакционный раствор охлаждают, подкисл ют 6 н. сол ной кислотой и экстрагируют трем  порци ми по 100 мл дихлорметана. Органическую фазу сушат над сульфатом натри , выпаривают до сухого состо ни  с получением 6,3 г темного твердого продукта. Этот твердый продукт растирают в порошок в гор чем серном эфире с получением
1,00 г вышеуказанного соединени , температура плавлени  которого составл ет 185-189°С; 1,26 г дополнительно этого продукта получают хроматографической силикагелевой обработкой маточного раствора.
Общий выход продукта равен 42,3%.
Результаты элементного анализа дл  С22Нзо04, %:
Вычислено, %: С 73,71; Н 8,44. Найдено, %: С 78,41; Н 8,37.
Подобным же образом с использованием соответствующих исходных реагентов примера 7 получают следующие соединени :
dl-da, - дигидро-1-окси-6,6-диметил-3-(1метил-4 - фенилбутокси)-6Н - дибензо Ь,
пиран-9(8Н)-он; т. пл. 140--168°С.
Результаты элементного анализа дл  С2бНзо04, %:
Вычислено, %: С 76,82; Н 7,44.
Найдено, %: С 76,74; Н 7,48.
dl-6a, 7 - Дигидро - 1 - окси-6,6-диметил-3 (1 - метил-3 - фенилбутокси)-6Н - дибензо й,й пиран-9(8Н)-он; т. пл. 163°С.
,7-Дигидро - 1-окси-6,6 - диметил-3циклогексилокси - 6Н - дибензс &,й пиран-9 (8Н)-он; т. пл. 259-254С.
dl-6a,7 - Дигидро- 1-окси-6,6 - диметил-3 (1 - метил-3-феноксипропил)-6Н - дибензо ,й пиран-9(8Н)-он, светло-желтый твердый продукт; т. пл. 203-206°С.
Результаты элементного анализа дл 
С25Н2804, %:
Вычислено, %: С 76,50; Н 7,19. Найдено, %: С 76,33; Н 7,12.

Claims (1)

1. Вейганд-Хильгетаг. Методы эксперимента в органической химии. М., «Хими , 1968, с. 706.
SU772506503A 1975-11-03 1977-07-26 Способ получени производных дибензо( )пиран-9(8н)-она SU677661A3 (ru)

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SU762416855A SU843748A3 (ru) 1975-11-03 1976-11-03 Способ получени производных дибензо( )пирана
SU772506503A SU677661A3 (ru) 1975-11-03 1977-07-26 Способ получени производных дибензо( )пиран-9(8н)-она
SU772505754A SU677660A3 (ru) 1975-11-03 1977-07-29 Способ получени производных хроманона
SU782579903A SU784772A4 (ru) 1975-11-03 1978-02-16 Способ получени производных дибензо пирана

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SU772505754A SU677660A3 (ru) 1975-11-03 1977-07-29 Способ получени производных хроманона
SU782579903A SU784772A4 (ru) 1975-11-03 1978-02-16 Способ получени производных дибензо пирана

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ZA (1) ZA766281B (ru)

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JPH0765890A (ja) * 1993-08-26 1995-03-10 Sumitomo Wiring Syst Ltd コネクタ
JP2988237B2 (ja) * 1994-01-31 1999-12-13 住友電装株式会社 簡易防水コネクタ
JP5037799B2 (ja) * 2005-06-30 2012-10-03 パナソニック株式会社 テレビコンセント
JP2021196016A (ja) 2020-06-16 2021-12-27 株式会社アイシン シフト装置

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CS207571B2 (en) 1981-08-31
NO148745B (no) 1983-08-29
PT65781B (en) 1978-05-10
DD129214A5 (de) 1978-01-04
IE43700L (en) 1977-05-03
ES452772A1 (es) 1978-02-16
HU178321B (en) 1982-04-28
DD137837A5 (de) 1979-09-26
DK495876A (da) 1977-05-04
JPS5943958B2 (ja) 1984-10-25
FI763131A (ru) 1977-05-04
ZA766281B (en) 1977-09-28
PT65781A (en) 1976-12-01
SU784772A4 (ru) 1980-11-30
PH16788A (en) 1984-02-28
BG27552A3 (en) 1979-11-12
NO148745C (no) 1983-12-07
IE43700B1 (en) 1981-05-06
JPS5943955B2 (ja) 1984-10-25
PL193435A1 (ru) 1980-01-28
CH622790A5 (en) 1981-04-30
JPS5277065A (en) 1977-06-29
PH14811A (en) 1981-12-14
YU268176A (en) 1983-10-31
JPS5589280A (en) 1980-07-05
ES462783A1 (es) 1978-06-01
BG28058A4 (en) 1980-02-25
RO71411A (ro) 1982-12-06
PL125297B1 (en) 1983-04-30
DD143774A5 (de) 1980-09-10
SU843748A3 (ru) 1981-06-30
JPS56103173A (en) 1981-08-18
NO763725L (ru) 1977-05-04
ES462784A1 (es) 1978-06-01
IL50717A0 (en) 1976-12-31
AR220521A1 (es) 1980-11-14
PH14383A (en) 1981-06-24
IL50717A (en) 1981-09-13
SE7611275L (sv) 1977-06-27
GR65202B (en) 1980-07-29
SU677660A3 (ru) 1979-07-30
RO75876A (ro) 1981-05-30
EG12648A (en) 1979-06-30
RO76006A (ro) 1981-03-30
SE432251B (sv) 1984-03-26
CA1099269A (en) 1981-04-14
RO76124A (ro) 1981-04-30
BG28057A4 (en) 1980-02-25
JPS564555B2 (ru) 1981-01-30
NZ182368A (en) 1978-04-03

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