IE35258B1 - Process for the manufacture of optically active bicycloalkane derivatives - Google Patents
Process for the manufacture of optically active bicycloalkane derivativesInfo
- Publication number
- IE35258B1 IE35258B1 IE298/71A IE29871A IE35258B1 IE 35258 B1 IE35258 B1 IE 35258B1 IE 298/71 A IE298/71 A IE 298/71A IE 29871 A IE29871 A IE 29871A IE 35258 B1 IE35258 B1 IE 35258B1
- Authority
- IE
- Ireland
- Prior art keywords
- chloro
- indanedione
- dihydro
- phenylenedioxy
- ortho
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- -1 amino compound Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002500 ions Chemical class 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- VSMOENVRRABVKN-UHFFFAOYSA-N (+/-)-matsutakeol Natural products CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 abstract 1
- VSMOENVRRABVKN-MRVPVSSYSA-N 1-Octen-3-ol Natural products CCCCC[C@H](O)C=C VSMOENVRRABVKN-MRVPVSSYSA-N 0.000 abstract 1
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- YDXQPTHHAPCTPP-UHFFFAOYSA-N 3-Octen-1-ol Natural products CCCCC=CCCO YDXQPTHHAPCTPP-UHFFFAOYSA-N 0.000 abstract 1
- NERGSGSEJNCZBN-UHFFFAOYSA-N 4,7a-dimethyl-2,3,6,7-tetrahydroindene-1,5-dione Chemical compound C1CC(=O)C(C)=C2CCC(=O)C21C NERGSGSEJNCZBN-UHFFFAOYSA-N 0.000 abstract 1
- FONYCLVDWNUHJV-UHFFFAOYSA-N 5-chlorohex-4-en-1-ol Chemical compound ClC(=CCCCO)C FONYCLVDWNUHJV-UHFFFAOYSA-N 0.000 abstract 1
- DZDPKLKGFCOGLE-UHFFFAOYSA-N 5-chlorohex-4-enal Chemical compound CC(Cl)=CCCC=O DZDPKLKGFCOGLE-UHFFFAOYSA-N 0.000 abstract 1
- SJAZDJCBOMMENQ-UHFFFAOYSA-N 5-chlorohex-4-enoic acid Chemical compound CC(Cl)=CCCC(O)=O SJAZDJCBOMMENQ-UHFFFAOYSA-N 0.000 abstract 1
- XNVGQWCVYWJRMV-UHFFFAOYSA-N 7-chloroocta-1,6-dien-3-ol Chemical compound ClC(=CCCC(C=C)O)C XNVGQWCVYWJRMV-UHFFFAOYSA-N 0.000 abstract 1
- DDGKTVGLVOCFDX-UHFFFAOYSA-N 7-chloroocta-1,6-dien-3-one Chemical compound CC(Cl)=CCCC(=O)C=C DDGKTVGLVOCFDX-UHFFFAOYSA-N 0.000 abstract 1
- MYTKJBIMJTVIRA-UHFFFAOYSA-N 7a-ethyl-2,3,6,7-tetrahydroindene-1,5-dione Chemical compound C1CC(=O)C=C2CCC(=O)C21CC MYTKJBIMJTVIRA-UHFFFAOYSA-N 0.000 abstract 1
- SXNIGKOVRGHYPI-UHFFFAOYSA-N 8a-butyl-3,4,7,8-tetrahydro-2h-naphthalene-1,6-dione Chemical compound C1CC(=O)C=C2CCCC(=O)C21CCCC SXNIGKOVRGHYPI-UHFFFAOYSA-N 0.000 abstract 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 125000001931 aliphatic 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
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N caproic aldehyde Natural products CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VIMSMKCDOPNVCZ-UHFFFAOYSA-N diethyl 2-(3-chlorobut-2-enyl)propanedioate Chemical compound C(C)OC(=O)C(CC=C(C)Cl)C(=O)OCC VIMSMKCDOPNVCZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N n-hexyl alcohol Natural products CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 1
- KLTVSWGXIAYTHO-UHFFFAOYSA-N n-pentyl vinyl ketone Natural products CCCCCC(=O)C=C KLTVSWGXIAYTHO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/637—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing ten carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702014757 DE2014757A1 (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung optisch aktiver Bicycloalkan Derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35258L IE35258L (en) | 1971-09-20 |
| IE35258B1 true IE35258B1 (en) | 1975-12-24 |
Family
ID=5766475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE298/71A IE35258B1 (en) | 1970-03-20 | 1971-03-09 | Process for the manufacture of optically active bicycloalkane derivatives |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6042775B2 (ja) * | 1977-10-11 | 1985-09-25 | 三菱油化株式会社 | １，７−オクタジエン−３−オン及びその製造方法 |
| ZA814972B (en) * | 1980-07-30 | 1982-07-28 | Beecham Group Plc | Reduced naphthalenes,their preparation and use |
-
1970
- 1970-03-20 DE DE19702014757 patent/DE2014757A1/de not_active Withdrawn
- 1970-03-20 YU YU571/71A patent/YU35432B/xx unknown
-
1971
- 1971-02-26 ZA ZA711253A patent/ZA711253B/xx unknown
- 1971-03-09 IE IE298/71A patent/IE35258B1/xx unknown
- 1971-03-10 CS CS175971A patent/CS155969B2/cs unknown
- 1971-03-13 IT IT21726/71A patent/IT1047887B/it active
- 1971-03-15 CH CH370871A patent/CH549548A/xx not_active IP Right Cessation
- 1971-03-16 ES ES389292A patent/ES389292A1/es not_active Expired
- 1971-03-17 IL IL36432A patent/IL36432A/xx unknown
- 1971-03-18 PL PL1971147006A patent/PL83133B1/pl unknown
- 1971-03-18 DK DK131071A patent/DK142312C/da active
- 1971-03-19 BE BE764509A patent/BE764509A/xx unknown
- 1971-03-19 PH PH12310A patent/PH9907A/en unknown
- 1971-03-19 SE SE7103588A patent/SE374101B/xx unknown
- 1971-03-19 FR FR7109723A patent/FR2084893A5/fr not_active Expired
- 1971-03-19 AT AT240271A patent/AT305971B/de not_active IP Right Cessation
- 1971-03-20 JP JP1611071A patent/JPS546550B1/ja active Pending
- 1971-03-20 YU YU00571/71A patent/YU57171A/xx unknown
- 1971-03-22 NL NL7103841A patent/NL7103841A/xx not_active Application Discontinuation
- 1971-04-19 GB GB2406071*A patent/GB1352637A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7103841A (enrdf_load_stackoverflow) | 1971-09-22 |
| IL36432A (en) | 1975-10-15 |
| ZA711253B (en) | 1971-11-24 |
| IE35258L (en) | 1971-09-20 |
| YU35432B (en) | 1981-02-28 |
| DE2014757A1 (de) | 1971-10-07 |
| DK142312C (da) | 1981-03-23 |
| AT305971B (de) | 1973-03-26 |
| IT1047887B (it) | 1980-10-20 |
| JPS546550B1 (enrdf_load_stackoverflow) | 1979-03-29 |
| FR2084893A5 (enrdf_load_stackoverflow) | 1971-12-17 |
| GB1352637A (en) | 1974-05-08 |
| SU373936A3 (enrdf_load_stackoverflow) | 1973-03-12 |
| CH549548A (de) | 1974-05-31 |
| PH9907A (en) | 1976-06-06 |
| BE764509A (fr) | 1971-09-20 |
| IL36432A0 (en) | 1971-05-26 |
| CS155969B2 (enrdf_load_stackoverflow) | 1974-06-24 |
| YU57171A (en) | 1980-09-25 |
| SE374101B (enrdf_load_stackoverflow) | 1975-02-24 |
| ES389292A1 (es) | 1973-06-16 |
| DK142312B (da) | 1980-10-13 |
| PL83133B1 (enrdf_load_stackoverflow) | 1975-12-31 |
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