CN101195632B - 环烷基硼酸类化合物的合成方法 - Google Patents
环烷基硼酸类化合物的合成方法 Download PDFInfo
- Publication number
- CN101195632B CN101195632B CN2006101193685A CN200610119368A CN101195632B CN 101195632 B CN101195632 B CN 101195632B CN 2006101193685 A CN2006101193685 A CN 2006101193685A CN 200610119368 A CN200610119368 A CN 200610119368A CN 101195632 B CN101195632 B CN 101195632B
- Authority
- CN
- China
- Prior art keywords
- boric acid
- cycloalkyl
- compound
- borate
- magnesium
- Prior art date
- 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.)
- Active
Links
- -1 cycloalkyl boric acid compound Chemical class 0.000 title claims abstract description 74
- 239000004327 boric acid Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title description 19
- 230000002194 synthesizing effect Effects 0.000 title 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 24
- 239000011777 magnesium Substances 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 92
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 46
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000010189 synthetic method Methods 0.000 claims description 9
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 8
- RVQXGFOIBYLZMH-UHFFFAOYSA-N Br.C1CC1 Chemical compound Br.C1CC1 RVQXGFOIBYLZMH-UHFFFAOYSA-N 0.000 claims description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims description 7
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 4
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 claims description 4
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 claims description 4
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 claims description 4
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 claims description 4
- NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 claims description 3
- VEZNCHDBSQWUHQ-UHFFFAOYSA-N chlorocyclopropane Chemical compound ClC1CC1 VEZNCHDBSQWUHQ-UHFFFAOYSA-N 0.000 claims description 3
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 claims description 3
- VLODBNNWEWTQJX-UHFFFAOYSA-N iodocyclopropane Chemical compound IC1CC1 VLODBNNWEWTQJX-UHFFFAOYSA-N 0.000 claims description 3
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 claims description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 16
- 238000001308 synthesis method Methods 0.000 abstract 2
- 238000003756 stirring Methods 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 239000011630 iodine Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000005903 acid hydrolysis reaction Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 238000006386 neutralization reaction Methods 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- CXBGICCKHLLDGX-UHFFFAOYSA-N cyclobutyloxyboronic acid Chemical compound OB(O)OC1CCC1 CXBGICCKHLLDGX-UHFFFAOYSA-N 0.000 description 6
- WZRXFPOWHQQSRJ-UHFFFAOYSA-N cyclohexyloxyboronic acid Chemical compound OB(O)OC1CCCCC1 WZRXFPOWHQQSRJ-UHFFFAOYSA-N 0.000 description 6
- WEUGCOVWGIARNP-UHFFFAOYSA-N cyclopentyloxyboronic acid Chemical compound OB(O)OC1CCCC1 WEUGCOVWGIARNP-UHFFFAOYSA-N 0.000 description 6
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OGACEQYPRIYUFN-UHFFFAOYSA-M I[Mg]C1CC1 Chemical compound I[Mg]C1CC1 OGACEQYPRIYUFN-UHFFFAOYSA-M 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- VXDKITOEYDGCLA-UHFFFAOYSA-M [I-].C1(CCC1)[Mg+] Chemical compound [I-].C1(CCC1)[Mg+] VXDKITOEYDGCLA-UHFFFAOYSA-M 0.000 description 2
- JTRPHJCURPRSQE-UHFFFAOYSA-N [Mg].I(=O)(=O)OC1CCCCC1 Chemical compound [Mg].I(=O)(=O)OC1CCCCC1 JTRPHJCURPRSQE-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BBWMASBANDIFMV-UHFFFAOYSA-N ethyl 4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C1(C(=O)OCC)CC[NH2+]CC1 BBWMASBANDIFMV-UHFFFAOYSA-N 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- KBMKSMGEPGPCPV-UHFFFAOYSA-M magnesium;cyclobutane;chloride Chemical compound [Mg+2].[Cl-].C1C[CH-]C1 KBMKSMGEPGPCPV-UHFFFAOYSA-M 0.000 description 2
- AAWGSOZCJNFZAG-UHFFFAOYSA-M magnesium;cyclopropane;chloride Chemical compound [Mg+2].[Cl-].C1C[CH-]1 AAWGSOZCJNFZAG-UHFFFAOYSA-M 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LKXYJYDRLBPHRS-UHFFFAOYSA-N bromocyclopropane Chemical compound BrC1CC1 LKXYJYDRLBPHRS-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- QRUDPBHCPMSJFN-UHFFFAOYSA-M magnesium;cyclobutane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]C1 QRUDPBHCPMSJFN-UHFFFAOYSA-M 0.000 description 1
- CTUBACPFLHEREX-UHFFFAOYSA-M magnesium;cyclopentane;iodide Chemical compound [Mg+2].[I-].C1CC[CH-]C1 CTUBACPFLHEREX-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2006101193685A CN101195632B (zh) | 2006-12-08 | 2006-12-08 | 环烷基硼酸类化合物的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2006101193685A CN101195632B (zh) | 2006-12-08 | 2006-12-08 | 环烷基硼酸类化合物的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101195632A CN101195632A (zh) | 2008-06-11 |
CN101195632B true CN101195632B (zh) | 2011-09-14 |
Family
ID=39546275
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2006101193685A Active CN101195632B (zh) | 2006-12-08 | 2006-12-08 | 环烷基硼酸类化合物的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101195632B (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101863912A (zh) * | 2010-06-07 | 2010-10-20 | 苏州莱克施德药业有限公司 | 环丙基硼酸的制备方法 |
CN102757455B (zh) * | 2012-08-05 | 2015-06-03 | 黑龙江格林赫思生物科技有限公司 | 环丙基硼酸的制备方法 |
CN105001249B (zh) * | 2015-06-12 | 2017-03-01 | 沧州普瑞东方科技有限公司 | 一种制备环丙基硼酸的方法 |
CN109305983B (zh) * | 2018-12-23 | 2021-01-05 | 沧州普瑞东方科技有限公司 | 一种环丙基硼酸的合成方法 |
CN113735889B (zh) * | 2021-09-06 | 2024-03-26 | 大连双硼医药化工有限公司 | 一种合成环丙基硼酸的工艺方法 |
CN115286480A (zh) * | 2022-08-26 | 2022-11-04 | 北京格林凯默科技有限公司 | 4,4′-二氟联苯的制备方法 |
-
2006
- 2006-12-08 CN CN2006101193685A patent/CN101195632B/zh active Active
Non-Patent Citations (1)
Title |
---|
Debra J.Wallace et al.Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions.《Tetrahedron Letters》.2002,第43卷6987-6990. * |
Also Published As
Publication number | Publication date |
---|---|
CN101195632A (zh) | 2008-06-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101195632B (zh) | 环烷基硼酸类化合物的合成方法 | |
CN104370755B (zh) | 一种光学活性的3‑氨基丁醇和3‑氨基丁酸的制备方法 | |
CN101495444A (zh) | 用于制备光学活性环丙胺的方法 | |
CN107353189A (zh) | 制备3, 5‑二氯‑a‑(三氟甲基)苯乙烯的方法 | |
CN104478793A (zh) | 一种2,3,5-三氯吡啶的合成方法 | |
CN109485625A (zh) | 1’-氯-8-溴二苯并呋喃的制备方法 | |
CN101671242B (zh) | 反-4-(反-4’-烷基环己基)环己基甲醛的合成方法 | |
CN102161672A (zh) | 三苯基硅醇的制备方法 | |
CN113666915A (zh) | 一种泊沙康唑中间体的制备方法 | |
CN1226259C (zh) | 一种1,2-戊二醇的制备方法 | |
CN103361388B (zh) | L-环状烷基氨基酸的合成方法及具有其的药物组合物 | |
CN102766156B (zh) | 四甲基二乙烯基二硅氮烷的制备方法 | |
CN102757455B (zh) | 环丙基硼酸的制备方法 | |
CN104650013A (zh) | 一种高选择性的(S)-β-羟基-γ-丁内酯简便制备方法 | |
CN109942393B (zh) | 1,1,1-三氟丙酮的制备方法 | |
CN105753741A (zh) | 一种抗心衰药物Sacubitril中间体的制备方法 | |
CN103540324B (zh) | 一种乙烯基环己基甲醚类液晶化合物及其制备方法 | |
CN105017099A (zh) | 一种西他列汀手性中间体及不对称合成方法 | |
CN101370759B (zh) | 制备卤素取代的苯二甲醇的方法 | |
CN101519351B (zh) | 一种高烯丙基醇酯的制备方法 | |
CN104926707B (zh) | 一种药物中间体的合成方法 | |
CN105198692A (zh) | 一种不对称催化合成(s)-芳姜黄烯的方法 | |
CN106167480A (zh) | 一种卡格列净中间体2‑(4‑氟苯基)噻吩的制备方法 | |
CN109651194B (zh) | 一种(e)-4-芳基-3-丁烯腈化合物的合成方法 | |
CN102924201B (zh) | 一种制备全氟烷基烷基酮化合物的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20171012 Address after: 201203 Fengxian District, United North Road, No. 99, Shanghai Patentee after: Kaihui Pharmaceutical (Shanghai) Co.,Ltd. Address before: 201203, room 965, 301 Harley Road, Zhangjiang hi tech park, Shanghai Patentee before: Shanghai ChemPartner Co.,Ltd. |
|
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: Building 3, No. 99 Lianhe North Road, Fengxian District, Shanghai, 2014 Patentee after: Shanghai Boteng Zhituo Pharmaceutical Technology Co.,Ltd. Address before: No. 99, Lianhe North Road, Fengxian District, Shanghai 201203 Patentee before: Kaihui Pharmaceutical (Shanghai) Co.,Ltd. |