KR900006311A - 5-치환된-3-푸르알데히드의 제조방법 - Google Patents
5-치환된-3-푸르알데히드의 제조방법 Download PDFInfo
- Publication number
- KR900006311A KR900006311A KR1019890014842A KR890014842A KR900006311A KR 900006311 A KR900006311 A KR 900006311A KR 1019890014842 A KR1019890014842 A KR 1019890014842A KR 890014842 A KR890014842 A KR 890014842A KR 900006311 A KR900006311 A KR 900006311A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- trimethylsilyl
- hydroxy
- electrophilic
- compound
- Prior art date
Links
- -1 5-substituted-3-furaldehyde Chemical class 0.000 title claims abstract 7
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims abstract 2
- AXSMTZCJJBPZAA-UHFFFAOYSA-N lithium;morpholin-4-ide Chemical compound [Li]N1CCOCC1 AXSMTZCJJBPZAA-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 1
- 229920003189 Nylon 4,6 Polymers 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NEHPZXVWPQEZDM-UHFFFAOYSA-N purine-3-carbaldehyde Chemical compound O=CN1C=NC=C2N=CN=C12 NEHPZXVWPQEZDM-UHFFFAOYSA-N 0.000 claims 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012039 electrophile Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 3-푸르알데히드를 (1) 리튬 모르폴라이드와 반응시키고, 이어서 (2) 2급-부틸리튬과 반응시킨 후, (3) 친전자성 물질과 반응시킴을 특징으로 하여, 다음 일반식(I)의 화합물을 제조하는 방법.상기식에서 E는 친전자성 그룹이다.
- 제 1 항에 있어서, E가 트리알킬실릴 ; 트리알킬스타닐 ; C1-20알킬 ; C1-20알케닐 또는 알키닐(여기에서 이중결합 또는 3중결합은 C2또는 그 이상의 탄소에 존재한다) ; 할로, 저급알킬 또는 저급알콕시에 의해 페닐환이 임의 치환된 벤질 ; N-알킬 카바모일 ; 알킬머캅토 ; 페닐머캅토 ; 또는 알카노일인 방법.
- 제 2 항에 있어서, E가 트리메틸실릴, 트리에틸실릴, 또는 t-부틸 디메틸실릴인 방법.
- 제 3 항에 있어서, E가 트리메틸실릴이고, 친전자성 물질이 트리메틸실릴 클로라이드인 방법.
- 제 2 항에 있어서, E가 트리부틸 스타닐인 방법.
- 제 2 항에 있어서, E가 옥틸, 1-하이드록시-1-메틸데실 또는 1-하이드록시 헥실인 방법.
- 제 2 항에 있어서, E가 (4-브로모페닐)-1-하이드록시 메틸인 방법.
- 제 1 항에 있어서, 친전자성 물질이 할라이드, 알데히드, 케톤, 이소시아네이트, 에폭사이드, 디설파이드 또는 에스테르인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US259225 | 1988-10-18 | ||
US07/259,225 US4935530A (en) | 1988-10-18 | 1988-10-18 | Process for preparing 5-substituted-3-furaldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
KR900006311A true KR900006311A (ko) | 1990-05-07 |
Family
ID=22984077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019890014842A KR900006311A (ko) | 1988-10-18 | 1989-10-16 | 5-치환된-3-푸르알데히드의 제조방법 |
Country Status (19)
Country | Link |
---|---|
US (1) | US4935530A (ko) |
EP (1) | EP0365256B1 (ko) |
JP (1) | JPH02164876A (ko) |
KR (1) | KR900006311A (ko) |
CN (1) | CN1023802C (ko) |
AT (1) | ATE94552T1 (ko) |
AU (1) | AU614474B2 (ko) |
CA (1) | CA2000677A1 (ko) |
DE (1) | DE68909166T2 (ko) |
DK (1) | DK517889A (ko) |
ES (1) | ES2044137T3 (ko) |
FI (1) | FI894924A0 (ko) |
HU (1) | HU204806B (ko) |
IE (1) | IE63693B1 (ko) |
IL (1) | IL91981A0 (ko) |
NO (1) | NO172799C (ko) |
NZ (1) | NZ231026A (ko) |
PT (1) | PT92016B (ko) |
ZA (1) | ZA897768B (ko) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5134128A (en) * | 1987-06-08 | 1992-07-28 | Allergan, Inc. | Anti-inflammatory furanones |
US5043457A (en) * | 1990-04-17 | 1991-08-27 | Allergan, Inc. | 2(5H)-furanones substituted in the 3 position, as Ca2+ channel antagonists and anti-inflammatory agents |
US5171863A (en) * | 1987-06-08 | 1992-12-15 | Allergan, Inc. | Intermediates for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents |
US5082954A (en) * | 1987-06-08 | 1992-01-21 | Allergan, Inc. | Intermediates and processes for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents |
US5322953A (en) * | 1987-06-08 | 1994-06-21 | Allergan, Inc. | 2-trialkylsilyl-3-furaldehydes |
US5037811A (en) * | 1990-04-17 | 1991-08-06 | Allergan, Inc. | 4-(oxygen, sulfur or nitrogen substituted)-methyl 5-hydroxy-2(5H)-furanones as anti-inflammatory agents |
US5045564A (en) * | 1988-12-07 | 1991-09-03 | Allergan, Inc. | Anti-inflammatory 2-furanones |
US5112853A (en) * | 1989-11-20 | 1992-05-12 | Allergan, Inc. | Anti-inflammatory furanone compounds |
US5258400A (en) * | 1989-11-20 | 1993-11-02 | Allergan, Inc. | Anti-inflammatory furanone compounds |
US5225571A (en) * | 1991-04-30 | 1993-07-06 | Allergan, Inc. | Substituted dihydroxy-bis-[5-hydroxy-2(5H)-furanone-4-yl]-alkanes as anti-inflammatory agents |
US5183906A (en) * | 1991-04-30 | 1993-02-02 | Allergan, Inc. | 2- and 5-alkyl and phenyl substituted 4-(1-hydroxy, 1-acyloxy or 1-carbamoyloxy)-5-hydroxy-2 (5h)-furanones as anti-inflammatory agents |
US5169963A (en) * | 1991-08-30 | 1992-12-08 | Allergan, Inc. | Di-(5-hydroxy-2(5H)2-oxo-4-furyl)alkylmethyl-alpha,omega alkanedioates and N,N-bis-(5-hydroxy-2(5H)2-oxo-4-furyl)alkylmethyl-alpha,omega-dialkanoic acid amides as anti-inflammatory agents |
US5171864A (en) * | 1991-08-30 | 1992-12-15 | Allergan, Inc. | Di-(5-hydroxy-2(5H)-2-oxo-4-furyl)methyl-alpha,omega alkane-dioates and N,N-bis-(5-hydroxy-2(5H)-2-oxo-4-furyl)methyl-alpha,omega-dialkanoic acid amides as anti-inflammatory agents |
US5268387A (en) * | 1992-04-24 | 1993-12-07 | Allergan, Inc. | Pharmaceutical compositions and method for administering 3 and 4-substituted 2(5H)-furanones to a mammal for inhibiting bone loss |
US5451686A (en) * | 1994-04-15 | 1995-09-19 | Allergan, Inc. | 3 and 5 alkyl and phenyl 4-(hydroxy or acyloxy)-alkyl substituted 2(5H)-furanones as anti-inflammatory agents |
US5639468A (en) * | 1995-06-07 | 1997-06-17 | University Of Southern California | Method for reducing or preventing post-surgical adhesion formation using manoalide and analogs thereof |
US7317116B2 (en) * | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
US7393963B2 (en) * | 2004-12-10 | 2008-07-01 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
KR101463933B1 (ko) * | 2012-08-14 | 2014-11-26 | 한국과학기술원 | 5-치환된 또는 2,5-치환된 3-푸르알데히드 유도체의 제조방법 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4221585A (en) * | 1978-08-04 | 1980-09-09 | E. I. Du Pont De Nemours And Company | N-[(2,6-Dimethoxypyrimidin-4-yl)]aminocarbonyl benzene sulfonamides and their herbicidal compositions and methods of use |
US4195026A (en) * | 1978-12-04 | 1980-03-25 | Iowa State University Research Foundation, Inc. | Substituted furans from butenolides |
US4500520A (en) * | 1983-03-01 | 1985-02-19 | E. I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic silylfurans |
WO1987006127A1 (en) * | 1986-04-07 | 1987-10-22 | The Upjohn Company | Anthelmintic acylhydrazones, method of use and compositions |
GB8609452D0 (en) * | 1986-04-17 | 1986-05-21 | Ici Plc | Fungicides |
CA1329390C (en) * | 1987-06-08 | 1994-05-10 | John N. Bonfiglio | Anti-inflammatory furanones |
-
1988
- 1988-10-18 US US07/259,225 patent/US4935530A/en not_active Expired - Lifetime
-
1989
- 1989-10-13 IL IL91981A patent/IL91981A0/xx not_active IP Right Cessation
- 1989-10-13 CA CA002000677A patent/CA2000677A1/en not_active Abandoned
- 1989-10-13 ZA ZA897768A patent/ZA897768B/xx unknown
- 1989-10-16 KR KR1019890014842A patent/KR900006311A/ko not_active Application Discontinuation
- 1989-10-16 NZ NZ231026A patent/NZ231026A/en unknown
- 1989-10-16 DE DE89310601T patent/DE68909166T2/de not_active Expired - Fee Related
- 1989-10-16 EP EP89310601A patent/EP0365256B1/en not_active Expired - Lifetime
- 1989-10-16 ES ES89310601T patent/ES2044137T3/es not_active Expired - Lifetime
- 1989-10-16 AT AT89310601T patent/ATE94552T1/de not_active IP Right Cessation
- 1989-10-17 PT PT92016A patent/PT92016B/pt not_active IP Right Cessation
- 1989-10-17 HU HU895337A patent/HU204806B/hu not_active IP Right Cessation
- 1989-10-17 FI FI894924A patent/FI894924A0/fi not_active Application Discontinuation
- 1989-10-17 NO NO894133A patent/NO172799C/no unknown
- 1989-10-17 AU AU42968/89A patent/AU614474B2/en not_active Ceased
- 1989-10-17 IE IE333589A patent/IE63693B1/en not_active IP Right Cessation
- 1989-10-18 JP JP1274778A patent/JPH02164876A/ja active Pending
- 1989-10-18 DK DK517889A patent/DK517889A/da not_active Application Discontinuation
- 1989-10-18 CN CN89108793A patent/CN1023802C/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
FI894924A0 (fi) | 1989-10-17 |
NO172799B (no) | 1993-06-01 |
NO894133L (no) | 1990-04-19 |
AU4296889A (en) | 1990-05-10 |
ATE94552T1 (de) | 1993-10-15 |
ES2044137T3 (es) | 1994-01-01 |
IE893335L (en) | 1990-04-18 |
DE68909166T2 (de) | 1994-02-10 |
US4935530A (en) | 1990-06-19 |
DK517889D0 (da) | 1989-10-18 |
HU204806B (en) | 1992-02-28 |
EP0365256A1 (en) | 1990-04-25 |
EP0365256B1 (en) | 1993-09-15 |
CN1023802C (zh) | 1994-02-16 |
HUT51266A (en) | 1990-04-28 |
DE68909166D1 (de) | 1993-10-21 |
PT92016B (pt) | 1995-06-30 |
PT92016A (pt) | 1990-04-30 |
JPH02164876A (ja) | 1990-06-25 |
IE63693B1 (en) | 1995-05-31 |
IL91981A0 (en) | 1990-07-12 |
AU614474B2 (en) | 1991-08-29 |
ZA897768B (en) | 1990-07-25 |
DK517889A (da) | 1990-04-19 |
CN1042154A (zh) | 1990-05-16 |
NO894133D0 (no) | 1989-10-17 |
CA2000677A1 (en) | 1990-04-18 |
NO172799C (no) | 1993-09-08 |
HU895337D0 (en) | 1990-01-28 |
NZ231026A (en) | 1991-05-28 |
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Legal Events
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WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |