SU735167A3 - Способ получени 9,12-мостиковых этаноантраценов - Google Patents

Способ получени 9,12-мостиковых этаноантраценов Download PDF

Info

Publication number: SU735167A3
Authority: SU; USSR - Soviet Union
Prior art keywords: alkyl; cycloalkyl; benzyl; spectrum; lower alkyl
Prior art date: 1973-11-21

Application number

SU742076512A

Other languages

English (en)

Russian (ru)

Inventor

Сайганек Энгелберт

Original Assignee

Е.И.Дю Пон Дэ Немур Энд Компани (Фирма)

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.)

1973-11-21

Filing date

1974-11-19

Publication date

1980-05-15

1974-11-19 Application filed by Е.И.Дю Пон Дэ Немур Энд Компани (Фирма) filed Critical Е.И.Дю Пон Дэ Немур Энд Компани (Фирма)

1980-05-15 Application granted granted Critical

1980-05-15 Publication of SU735167A3 publication Critical patent/SU735167A3/ru

Links

238000000034 method Methods 0.000 title claims description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
238000010438 heat treatment Methods 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
238000005698 Diels-Alder reaction Methods 0.000 claims description 3
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
238000005648 named reaction Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 8
-1 sulphamyl Chemical group 0.000 abstract description 8
125000004429 atom Chemical group 0.000 abstract description 5
229910052799 carbon Inorganic materials 0.000 abstract description 5
229910052757 nitrogen Inorganic materials 0.000 abstract description 5
239000002253 acid Substances 0.000 abstract description 2
150000001454 anthracenes Chemical class 0.000 abstract description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
125000004432 carbon atom Chemical group C* 0.000 abstract 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
150000001721 carbon Chemical group 0.000 abstract 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
238000001228 spectrum Methods 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 12
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 9
150000007530 organic bases Chemical class 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 5
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
REJFOBQJXSGDSB-UHFFFAOYSA-N anthracene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=C(C=CC=C3)C3=CC2=C1 REJFOBQJXSGDSB-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
OOFMIUZJZJLORQ-UHFFFAOYSA-N cyclobuta[a]anthracene Chemical compound C1=CC2=CC3=CC=CC=C3C=C2C2=C1C=C2 OOFMIUZJZJLORQ-UHFFFAOYSA-N 0.000 description 2
UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000006412 Alper carbonylation reaction Methods 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000218657 Picea Species 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
238000006480 benzoylation reaction Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910010277 boron hydride Inorganic materials 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Polymerisation Methods In General (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Compositions Of Macromolecular Compounds (AREA)

SU742076512A 1973-11-21 1974-11-19 Способ получени 9,12-мостиковых этаноантраценов SU735167A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US41780773A	1973-11-21	1973-11-21
US51102674A	1974-09-30	1974-09-30

Publications (1)

Publication Number	Publication Date
SU735167A3 true SU735167A3 (ru)	1980-05-15

Family

ID=27023866

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU742076512A SU735167A3 (ru)	1973-11-21	1974-11-19	Способ получени 9,12-мостиковых этаноантраценов

Country Status (21)

Country	Link
JP (2)	JPS5093964A (de)
AR (1)	AR208895A1 (de)
AT (1)	AT340406B (de)
CA (1)	CA1021331A (de)
CH (1)	CH605750A5 (de)
DD (1)	DD116035A5 (de)
DE (2)	DE2454634A1 (de)
DK (2)	DK602974A (de)
ES (1)	ES432124A1 (de)
FI (1)	FI61307C (de)
FR (2)	FR2251556B1 (de)
GB (1)	GB1470899A (de)
HU (1)	HU176770B (de)
IE (1)	IE40416B1 (de)
IL (1)	IL46087A (de)
LU (2)	LU71331A1 (de)
NL (2)	NL7415125A (de)
NO (1)	NO145658C (de)
PH (1)	PH14966A (de)
SE (1)	SE403775B (de)
SU (1)	SU735167A3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2907525B1 (de) *	2007-11-21	2018-05-16	University Of Georgia Research Foundation, Inc.	Dibenzocycloocten-verbindungen fuer bioorthogonale reaktionen

1974
- 1974-10-16 SE SE7413035A patent/SE403775B/xx unknown
- 1974-11-18 DE DE19742454634 patent/DE2454634A1/de not_active Withdrawn
- 1974-11-19 AT AT925674A patent/AT340406B/de not_active IP Right Cessation
- 1974-11-19 SU SU742076512A patent/SU735167A3/ru active
- 1974-11-19 IE IE2375/74A patent/IE40416B1/xx unknown
- 1974-11-19 CA CA214,129A patent/CA1021331A/en not_active Expired
- 1974-11-19 HU HU74DU230A patent/HU176770B/hu unknown
- 1974-11-20 NL NL7415125A patent/NL7415125A/xx not_active Application Discontinuation
- 1974-11-20 AR AR256588A patent/AR208895A1/es active
- 1974-11-20 PH PH16538A patent/PH14966A/en unknown
- 1974-11-20 FR FR7438118A patent/FR2251556B1/fr not_active Expired
- 1974-11-20 IL IL46087A patent/IL46087A/en unknown
- 1974-11-20 NO NO744170A patent/NO145658C/no unknown
- 1974-11-20 DK DK602974A patent/DK602974A/da unknown
- 1974-11-20 ES ES432124A patent/ES432124A1/es not_active Expired
- 1974-11-20 DD DD182469A patent/DD116035A5/xx unknown
- 1974-11-20 DE DE19742455049 patent/DE2455049A1/de active Pending
- 1974-11-20 DK DK602874A patent/DK602874A/da unknown
- 1974-11-20 FI FI3349/74A patent/FI61307C/fi active
- 1974-11-20 GB GB5031874A patent/GB1470899A/en not_active Expired
- 1974-11-21 LU LU71331A patent/LU71331A1/xx unknown
- 1974-11-21 LU LU71323A patent/LU71323A1/xx unknown
- 1974-11-21 FR FR7438346A patent/FR2251326A1/fr not_active Withdrawn
- 1974-11-21 NL NL7415186A patent/NL7415186A/xx unknown
- 1974-11-21 CH CH1552774A patent/CH605750A5/xx not_active IP Right Cessation
- 1974-11-21 JP JP49135020A patent/JPS5093964A/ja active Pending
- 1974-11-21 JP JP49135022A patent/JPS5093965A/ja active Pending

Also Published As

Publication number	Publication date
ATA925674A (de)	1977-04-15
LU71323A1 (de)	1975-05-28
DD116035A5 (de)	1975-11-05
HU176770B (en)	1981-05-28
FI334974A7 (de)	1975-05-22
NL7415125A (nl)	1975-05-23
DE2454634A1 (de)	1975-05-22
DE2455049A1 (de)	1975-05-22
CA1021331A (en)	1977-11-22
DK602974A (de)	1975-07-21
IL46087A0 (en)	1975-03-13
FR2251556A1 (de)	1975-06-13
FI61307B (fi)	1982-03-31
SE7413035L (de)	1975-05-22
AR208895A1 (es)	1977-03-15
GB1470899A (en)	1977-04-21
LU71331A1 (de)	1975-05-28
FR2251556B1 (de)	1979-05-25
IE40416B1 (en)	1979-05-23
NO145658C (no)	1982-05-05
ES432124A1 (es)	1977-02-16
NO744170L (de)	1975-06-16
NL7415186A (nl)	1975-05-23
NO145658B (no)	1982-01-25
AU7550274A (en)	1976-05-20
FI61307C (fi)	1982-07-12
PH14966A (en)	1982-02-05
IE40416L (en)	1975-05-21
DK602874A (de)	1975-07-21
SE403775B (sv)	1978-09-04
IL46087A (en)	1977-12-30
CH605750A5 (de)	1978-10-13
JPS5093964A (de)	1975-07-26
FR2251326A1 (de)	1975-06-13
AT340406B (de)	1977-12-12
JPS5093965A (de)	1975-07-26

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