CN107849003A - 制备色原烷醇衍生物的新方法 - Google Patents
制备色原烷醇衍生物的新方法 Download PDFInfo
- Publication number
- CN107849003A CN107849003A CN201680044642.9A CN201680044642A CN107849003A CN 107849003 A CN107849003 A CN 107849003A CN 201680044642 A CN201680044642 A CN 201680044642A CN 107849003 A CN107849003 A CN 107849003A
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- Prior art keywords
- formula
- compound
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- chiral
- catalyst
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- Legal status (The legal status 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 status listed.)
- Pending
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- 238000000034 method Methods 0.000 title claims abstract description 41
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical class O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 238000006722 reduction reaction Methods 0.000 claims description 13
- 239000000852 hydrogen donor Substances 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012990 dithiocarbamate Substances 0.000 claims description 2
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- -1 chromanol derivative compound Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150110248A KR101769204B1 (ko) | 2015-08-04 | 2015-08-04 | 크로마놀 유도체의 신규한 제조방법 |
| KR10-2015-0110248 | 2015-08-04 | ||
| PCT/KR2016/008580 WO2017023124A1 (ko) | 2015-08-04 | 2016-08-03 | 크로마놀 유도체의 신규한 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107849003A true CN107849003A (zh) | 2018-03-27 |
Family
ID=57943342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680044642.9A Pending CN107849003A (zh) | 2015-08-04 | 2016-08-03 | 制备色原烷醇衍生物的新方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP6676146B2 (ko) |
| KR (1) | KR101769204B1 (ko) |
| CN (1) | CN107849003A (ko) |
| WO (1) | WO2017023124A1 (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113237970A (zh) * | 2021-04-23 | 2021-08-10 | 上海应用技术大学 | 一种5,7-二氟苯并二氢吡喃-4-醇的r、s异构体的高效液相色谱分离方法 |
| CN114222734A (zh) * | 2020-07-20 | 2022-03-22 | 杭州杜易科技有限公司 | 一种制备取代色满酮衍生物的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1926083A (zh) * | 2004-03-29 | 2007-03-07 | 财团法人名古屋产业科学研究所 | 光学活性醇的制造方法 |
| CN1968927A (zh) * | 2004-06-22 | 2007-05-23 | 诺瓦提斯公司 | 对映体选择性制备喹啉衍生物的方法 |
| WO2007072146A1 (en) * | 2005-12-19 | 2007-06-28 | Pfizer Japan Inc. | Chromane substituted benzimidazoles and their use as acid pump inhibitors |
| KR20080108129A (ko) * | 2006-03-17 | 2008-12-11 | 라퀄리아 파마 인코포레이티드 | 크로메인 유도체 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101130465B1 (ko) | 2005-12-30 | 2012-03-27 | 엘지전자 주식회사 | 스크롤 압축기의 과열방지장치 |
| WO2008059373A1 (en) * | 2006-11-17 | 2008-05-22 | Raqualia Pharma Inc. | Imidazo [1, 2-a] pyrazine derivatives and their use as acid pump antagonists |
| WO2008151927A2 (en) * | 2007-06-15 | 2008-12-18 | Nycomed Gmbh | 6-n-substituted benz imidazole derivatives as acid pump antagonists |
| TWI498330B (zh) * | 2010-08-04 | 2015-09-01 | Elanco Animal Health Ireland | 對芽孢梭菌屬具有抗菌活性之化合物 |
-
2015
- 2015-08-04 KR KR1020150110248A patent/KR101769204B1/ko active IP Right Grant
-
2016
- 2016-08-03 JP JP2018505683A patent/JP6676146B2/ja active Active
- 2016-08-03 CN CN201680044642.9A patent/CN107849003A/zh active Pending
- 2016-08-03 WO PCT/KR2016/008580 patent/WO2017023124A1/ko active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1926083A (zh) * | 2004-03-29 | 2007-03-07 | 财团法人名古屋产业科学研究所 | 光学活性醇的制造方法 |
| CN1968927A (zh) * | 2004-06-22 | 2007-05-23 | 诺瓦提斯公司 | 对映体选择性制备喹啉衍生物的方法 |
| WO2007072146A1 (en) * | 2005-12-19 | 2007-06-28 | Pfizer Japan Inc. | Chromane substituted benzimidazoles and their use as acid pump inhibitors |
| KR20080108129A (ko) * | 2006-03-17 | 2008-12-11 | 라퀄리아 파마 인코포레이티드 | 크로메인 유도체 |
Non-Patent Citations (1)
| Title |
|---|
| ROSARIO FERNÁNDEZ ET AL.: "Enantioselective synthesis of cis-a-substituted cycloalkanols and trans-cycloalkyl amines thereof", 《TETRAHEDRON》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114222734A (zh) * | 2020-07-20 | 2022-03-22 | 杭州杜易科技有限公司 | 一种制备取代色满酮衍生物的方法 |
| US11377434B2 (en) | 2020-07-20 | 2022-07-05 | Hangzhou Duyi Technology Co. Ltd. | Methods for preparing substituted chromanone derivatives |
| CN114222734B (zh) * | 2020-07-20 | 2023-12-08 | 杭州杜易科技有限公司 | 一种制备取代色满酮衍生物的方法 |
| CN113237970A (zh) * | 2021-04-23 | 2021-08-10 | 上海应用技术大学 | 一种5,7-二氟苯并二氢吡喃-4-醇的r、s异构体的高效液相色谱分离方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018525376A (ja) | 2018-09-06 |
| JP6676146B2 (ja) | 2020-04-08 |
| WO2017023124A1 (ko) | 2017-02-09 |
| KR101769204B1 (ko) | 2017-08-17 |
| KR20170016756A (ko) | 2017-02-14 |
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| CB02 | Change of applicant information |
Address after: Han Guoshouer Applicant after: Inoon Limited Address before: Han Guoshouer Applicant before: CJ HEALTHCARE Corp. |
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