CN102659707A - 一种手性化合物的制备及用途 - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
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- 238000000926 separation method Methods 0.000 claims abstract description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- QMXOFBXZEKTJIK-UHFFFAOYSA-N Glycinol Natural products C1=C(O)C=C2OCC3(O)C4=CC=C(O)C=C4OC3C2=C1 QMXOFBXZEKTJIK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
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- 230000009466 transformation Effects 0.000 claims description 3
- 238000006842 Henry reaction Methods 0.000 abstract description 3
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical compound OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 abstract 1
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- 238000003786 synthesis reaction Methods 0.000 description 3
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- ZZNSFVQRQDZGGX-KXXCBVSKSA-N (4z,6z,8e)-3-hydroxy-n-[(2e,4e,7r,9s)-6-hydroxy-9-[(7r,8s)-8-hydroxy-5,7-dimethyl-3,6-dioxo-2-oxa-5-azaspiro[3.4]octan-8-yl]-9-methoxy-7-methylnona-2,4-dienyl]-2,2,4-trimethyl-10-(1,3-oxazol-5-yl)deca-4,6,8-trienamide Chemical compound OC([C@H](C)C[C@H](OC)[C@@]1(O)C2(C(OC2)=O)N(C)C(=O)[C@@H]1C)\C=C\C=C\CNC(=O)C(C)(C)C(O)C(\C)=C/C=C\C=C\CC1=CN=CO1 ZZNSFVQRQDZGGX-KXXCBVSKSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
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- XUEWIQNQPBSCOR-UHFFFAOYSA-N 2-nitro-1-phenylethanol Chemical compound [O-][N+](=O)CC(O)C1=CC=CC=C1 XUEWIQNQPBSCOR-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000010485 C−C bond formation reaction Methods 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- XSSQCBJTQFPFFQ-UHFFFAOYSA-N Neooxazolomycin Natural products O1C(=O)C2(CO)N(C)C(=O)C(C)C2(O)C1CC(C)C(O)C=CC=CCNC(=O)C(C)(C)C(O)C(C)=CC=CC=CCC1=CN=CO1 XSSQCBJTQFPFFQ-UHFFFAOYSA-N 0.000 description 1
- WWMXIRNUPCVAQA-UHFFFAOYSA-N Oxazolomycin Natural products COC(CC(C)C(O)C=CC=CCNC(=O)C(C)(C)C(O)C(=C/C=CCC=Cc1ocnc1)C)C2(O)C(C)C(=O)N(C)C23COC3=O WWMXIRNUPCVAQA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
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- ZZNSFVQRQDZGGX-UHFFFAOYSA-N oxazolomycin A Natural products CC1C(=O)N(C)C2(C(OC2)=O)C1(O)C(OC)CC(C)C(O)C=CC=CCNC(=O)C(C)(C)C(O)C(C)=CC=CC=CCC1=CN=CO1 ZZNSFVQRQDZGGX-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
一种手性化合物的制备,其化学式如下:
Description
一、技术领域
本发明涉及一种化合物的制备方法及用途,特别涉及一种手性化合物的制备方法及用途,确切地说是一种手性2-羰基噁唑啉的合成方法及用途。
二、背景技术
手性2-羰基噁唑啉是重要的医药中间体,可用来合成抗癌药物等,是国内外研究的热点之一,其合成方法有多种【1-6】。
参考文献:
1. Interaction of substrate and catalyst during the formation of oxazolidinones from 2-aminoalcohols and diethyl carbonate using recyclable 1,3-dichlorodistannoxanes , Pulla, Sharon et al, Journal of Molecular Catalysis A: Chemical, 338(1-2), 33-43; 2011.
2. Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate, Yamada, Takeshi et al, Tetrahedron: Asymmetry, 19(24), 2789-2795; 2008.
3. Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from
phenylglycine Chavda, Sameer et al, Tetrahedron: Asymmetry, 19(13), 1536-1548; 2008.
4. Stereoselective Synthesis of Quaternary Center Bearing Azetines and Their β-Amino
Acid Derivatives MacNevin, Christopher J. et al, Journal of Organic Chemistry, 73(4),
1264-1269; 2008.
5. Kinetic Resolution of 2-Oxazolidinones via Catalytic, Enantioselective N-Acylation,
Birman, Vladimir B. et al, Journal of the American Chemical Society, 128(20), 6536-6537;
2006.
6. Parallel kinetic resolution of D-labelled 2-aryl-propionic and butanoic acids using
quasi-enantiomeric combinations of oxazolidin-2-ones Coulbeck, Elliot et al, Chirality,
22(2), 193-205; 2010.
申请人以7, 7, 8, 8-四氰基奎二甲烷与D-苯甘氨醇在105mol%氯化锌作催化剂下,得到了一种手性化合物 (R)-4-苯基噁唑啉基-2-酮。
三、发明内容
本发明旨在提供化合物手性化合物 (R)-4-苯基噁唑啉基-2-酮。所要解决的技术问题是一步合成得到目标产物。
一种手性化合物的制备是由7, 7, 8, 8-四氰基奎二甲烷与D-苯甘氨醇制备的由以下化学式所示的化合物:
(Ⅰ)
化学名称:(R)-4-苯基噁唑啉基-2-酮,简称化合物(I)。
本合成方法包括合成和分离,所述的合成用105mol% 氯化锌做催化剂,7,7,8,8-四氰基奎二甲烷4.90mmol,D-苯甘氨醇 90mmol,用50mL氯苯做溶剂,回流反应3天后,柱层析分离,用石油醚/二氯甲烷(1/1)洗脱,将收集的最后组分点自然挥发,得单晶(R)-4-苯基噁唑啉基-2-酮。
合成反应如下:
本合成方法一步得到目标产物,工艺简单,操作方便。
该化合物在苯甲醛的亨利反应中显示了一定的催化性能,其转化率达58%。
其反应机理可推测如下:
7, 7, 8, 8-四氰基奎二甲烷由于在空气及大量路易斯酸催化剂作用下不稳定,氰基首先生成甲酸,然后与大大过量的D-苯甘氨醇在氯化锌作用下进行缩合反应,甲酸中的羟基与D-苯甘氨醇中的氨基,及羟基分别脱去两分子水,又与水分子作用,得手性化合物 (R)-4-苯基噁唑啉基-2-酮,其反应过程如下:
四、附图说明
图1是(R)-4-苯基噁唑啉基-2-酮的X-衍射分析图。
五、具体实施方式
在100mL两口瓶中,加入无水ZnCl2 735.9mg (5.14 mmol), 50mL氯苯, 7, 7, 8, 8-四氰基奎二甲烷1.0g (4.90mmol), D-苯甘氨醇 10.0g, 将混合物在高温下回流72h, 停止反应,减压以除去溶剂, ,将剩余物用水溶解,并用CH2Cl2 (20mLx3) 萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/ 二氯甲烷(1:1)柱层析,得无色油状液体, 产率45 %; [a]5 D= -31.78o (c = 0.0472, CH2Cl2):1HNMR (500MHz, CDCl3, 27℃), δ (ppm) = 7.34~7.45 (m, 5H), 5.42 (s, 1H), 4.99 (t, J=0.5Hz, 1H), 4.78 (t, J=0.5Hz, 1H), 4.23 (t, J=0.5Hz, 1H), 13CNMR(125MHz, CDCl3, 27℃) 159.2, 139.1, 128.8, 128.5, 125.7, 72.2, 56.0; IR (KBr):3064, 3032, 2956, 2924, 2853, 1755, 1646, 1603, 1495, 1457, 1398, 1360, 1308, 1283, 1235, 1077, 1040, 960, 936, 924, 763, 700, 551, 492; HRMS: m/z (%): C9H9NO2, calcd for C9H9NO2 163.0633; found: 163.0638.
亨利反应应用
反应原理:
Henry反应是Louis Henry于1895年最早发现并命名的。它是基于羰基和含有α-活泼氢的硝基烷烃类化合物之间的碳碳键形成反应,其产物是一类含β-硝基醇的双官能团化合物。到目前为止它仍然是一种经典的碳碳键形成反应。 Henry反应中,含α-活泼氢的硝基化合物在碱等夺质子试剂作用下成为碳负离子,再进攻羰基形成新的碳碳键,而得到双官能团化合物β-硝基醇。反应方程式如下:
2-Nitro-1-phenylethanol的制备
2-硝基-1苯基乙醇的制备
取0.10mmol化合物(I)(催化用量为10%)于25mL的小烧瓶中,加入2毫升的甲醇溶液,然后,向上述溶液中加入0.1mL的苯甲醛与0.5mL的硝基甲烷,常温搅拌,反应72小时,用石油醚/二氯甲烷淋洗,进行柱层析, 转化率: 58%,1H NMR (300MHz, CDCl3) 7.28~7.32 (m, 5H, Ar-H), 5.32~5.35(d, J=9.18Hz, 1H, -CH), 4.38~4.56 (m, 2H, -CH2), 3.89(br, 1H, -OH).
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659706A (zh) * | 2012-05-10 | 2012-09-12 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN103641788A (zh) * | 2013-12-23 | 2014-03-19 | 罗梅 | 一种手性2-羰基噁唑啉的合成方法 |
CN105566243A (zh) * | 2016-01-15 | 2016-05-11 | 齐鲁天和惠世制药有限公司 | 从依折麦布生产废液中回收(s)-(+)-4-苯基-2-噁唑烷酮的方法 |
CN107652205A (zh) * | 2017-10-24 | 2018-02-02 | 合肥祥晨化工有限公司 | 一种亚胺晶体化合物的合成方法及用途 |
CN110272396A (zh) * | 2019-07-23 | 2019-09-24 | 合肥祥晨化工有限公司 | 一种手性2-羰基噁唑啉的合成方法及用途 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102225915A (zh) * | 2011-05-16 | 2011-10-26 | 罗梅 | 一种手性噁唑啉及其合成方法 |
CN102229604A (zh) * | 2011-04-22 | 2011-11-02 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN102382138A (zh) * | 2011-07-28 | 2012-03-21 | 罗梅 | 一种手性双膦酰二胺化合物及用途 |
CN102643246A (zh) * | 2012-03-22 | 2012-08-22 | 罗梅 | 一种手性2-羰基噁唑啉的合成方法 |
CN102659706A (zh) * | 2012-05-10 | 2012-09-12 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN102659633A (zh) * | 2012-04-12 | 2012-09-12 | 罗梅 | 一种手性酰铵盐的合成方法 |
-
2012
- 2012-04-26 CN CN201210124310.5A patent/CN102659707B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102229604A (zh) * | 2011-04-22 | 2011-11-02 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN102225915A (zh) * | 2011-05-16 | 2011-10-26 | 罗梅 | 一种手性噁唑啉及其合成方法 |
CN102382138A (zh) * | 2011-07-28 | 2012-03-21 | 罗梅 | 一种手性双膦酰二胺化合物及用途 |
CN102643246A (zh) * | 2012-03-22 | 2012-08-22 | 罗梅 | 一种手性2-羰基噁唑啉的合成方法 |
CN102659633A (zh) * | 2012-04-12 | 2012-09-12 | 罗梅 | 一种手性酰铵盐的合成方法 |
CN102659706A (zh) * | 2012-05-10 | 2012-09-12 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
Non-Patent Citations (1)
Title |
---|
THORSTEN BACH ET AL.: "Facial Diastereoselectivity in the Photocycloaddition of Chiral N-Acyl Enamines to Benzaldehyde", 《TETRAHEDRON》, vol. 54, 31 December 1998 (1998-12-31), pages 4507 - 4520 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659706A (zh) * | 2012-05-10 | 2012-09-12 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN102659706B (zh) * | 2012-05-10 | 2014-10-08 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN103641788A (zh) * | 2013-12-23 | 2014-03-19 | 罗梅 | 一种手性2-羰基噁唑啉的合成方法 |
CN103641788B (zh) * | 2013-12-23 | 2015-01-07 | 罗梅 | 一种手性2-羰基噁唑啉的合成方法 |
CN105566243A (zh) * | 2016-01-15 | 2016-05-11 | 齐鲁天和惠世制药有限公司 | 从依折麦布生产废液中回收(s)-(+)-4-苯基-2-噁唑烷酮的方法 |
CN107652205A (zh) * | 2017-10-24 | 2018-02-02 | 合肥祥晨化工有限公司 | 一种亚胺晶体化合物的合成方法及用途 |
CN110272396A (zh) * | 2019-07-23 | 2019-09-24 | 合肥祥晨化工有限公司 | 一种手性2-羰基噁唑啉的合成方法及用途 |
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