CN113214096A - 一种手性季铵盐的制备及用途 - Google Patents
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 title description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- -1 quaternary ammonium salt compound Chemical class 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 8
- NWYYWIJOWOLJNR-YFKPBYRVSA-N (2r)-2-amino-3-methylbutan-1-ol Chemical compound CC(C)[C@@H](N)CO NWYYWIJOWOLJNR-YFKPBYRVSA-N 0.000 claims abstract description 7
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011592 zinc chloride Substances 0.000 claims abstract description 5
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 238000010992 reflux Methods 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000002447 crystallographic data Methods 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DTAFQWDNWAXRLX-UHFFFAOYSA-N 2-phenyl-2-trimethylsilyloxyacetonitrile Chemical compound C[Si](C)(C)OC(C#N)C1=CC=CC=C1 DTAFQWDNWAXRLX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000004030 hiv protease inhibitor Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
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- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- 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
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- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
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Abstract
一种手性季铵盐化合物(I)的制备，其结构式如下：
该手性季铵盐化合物(I)的合成方法，用10mol％氯化锌做催化剂，首先加入无水ZnCl22mmol,50mL无水甲醇,氢氧化钠2.1639g,D‑缬氨醇1.5656g,将混合物在高温下回流60h,停止反应,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,将粗产品用二氯甲烷及无水乙醇重结晶，得无色晶体；该手性季铵盐化合物(I)的用途，其特征在于其在苯甲醛的腈硅化反应及在二苯甲酮腙的缩合反应中显示了良好的催化性能，其转化率分别高达71％及99％。
Description
一、技术领域
本发明涉及一种新化合物及其制备方法，特别涉及一种手性季铵盐化合物制备及用途，确切地说是一种手性(R)-缬氨醇甲酸铵盐的制备及用途。
二、背景技术
手性(R)-缬氨醇甲酸铵盐是重要的医药中间体，季铵盐是阳离子型表面活性剂的一个大类。其用途具有强烈的杀菌和抑霉防蛀性能。
参考文献：
1.N,N'-(Oxoethylene)bis(DL-3-phenylalanine)，Fones,Wm.S.,Journal ofthe American Chemical Society(1952),74,4708-9.
2.Preparation of optical activity 1，3-di(N-substituted amino)-4-phenylbutan-2-ol derivatives by reduction using metal hydrides,Yuasa,Yoshifumi；Konno,Masao；Sano,Noboru,Jpn.Kokai Tokkyo Koho(1997),JP 09249622 A19970922.
3.Preparation of amino acid amides as HIV protease inhibitors,Reed,Kathryn Lea；Talley,John Jeffrey,PCT Int.Appl.(1992),WO 9208700 A1 19920529。
申请人以D-缬氨醇与氢氧化钠在10mol％氯化锌作催化剂下，得到了一种手性(R)-缬氨醇甲酸铵盐化合物。
三、发明内容
本发明旨在提供化合物手性化合物。所要解决的技术问题是一步合成得到目标产物。
(一)本发明所称的化合物是以下化学式(Ⅰ)所示的化合物：
其化学名称：(1-羟基-3(R)-异丙基-2-氨基)-1-羟基-3(R)-异丙基-2-氨基甲酸铵盐。
本合成方法包括合成和分离，所述的合成用10mol％氯化锌做催化剂，首先加入无水 ZnCl2 2mmol,50mL无水甲醇,氢氧化钠2.1639g,D-缬氨醇1.5656g,将混合物在高温下回流 60h,停止反应.。将粗产品用二氯甲烷及无水乙醇重结晶，得无色晶体。其合成反应如下：
本合成方法一步得到目标产物，工艺简单，操作方便。
其反应机理可推测如下：
该反应机理复杂，可推测如下：D-缬氨醇由于在空气及10mol％路易斯酸催化剂氯化锌及大量氢氧化钠作用下不稳定，产生了小分子CO2，然后分别与两分子的D-缬氨醇作用，得稳定的手性化合物(1-羟基-3(R)-异丙基-2-氨基)-1-羟基-3(R)-异丙基甲酸铵盐。
该手性季铵盐在苯甲醛的腈硅化反应及二苯甲酮腙的缩合反应中显示了较好的催化性能，其转化率分别达71％及99％。
四、附图说明
图1是(1-羟基-3(R)-异丙基-2-氨基)-1-羟基-3(R)-异丙基甲酸铵盐的X-衍射分析图。
五、具体实施方式
在100mL两口瓶中,加入无水ZnCl2 26.92mg,50mL无水甲醇,氢氧化钠2.1639g,D-缬氨醇 1.5656g,将混合物在高温下回流60h,停止反应。减压以除去溶剂，将粗产品用二氯甲烷及无水乙醇重结晶，得无色晶体,产率：82％；m.p.:>220℃,[a]20 D＝-30.5°(c＝0.0492,THF)：1HNMR(600MHz,CDCl3,27℃),δ(ppm)＝4.70(s,3H)，3.45-3.47(m,1H),3.19-3.26(m,2H), 2.48(s,1H).1.74-1.76(m,1H),1.60-1.63(m,1H),0.80(d,7.6Hz,12H)；13CNMR(150MHz,CDCl3, 27℃)160.7,63.2,62.9,58.2,58.1,29.7,29.0,19.8,19.4,18.7,18.6；IR(ν,cm-1):3346,3244, 2920,2869,1621,1546,1462,1378,1317,1288,1243,1144,1119,1069,1042,1018,979,931, 822,713,648,578,539；ESI(m+1/e:C11H27N2O4:calcd.:251.1961；found:251.1861)；
该化合物晶体数据如下：
晶体典型的键长数据：
晶体典型的键角数据：
硅腈化反应应用
2-苯基-2-(三甲硅氧基)乙腈的制备
0.15mmol化合物I,苯甲醛0.1mL,TMSCN 0.3ml(3.3mmol)相继在20～30℃下加入，48h后，加入水淬灭经柱层后(石油醚/二氯甲烷：5/1)，得无色油状液体,转化率：71％，1HNMR (300MHz,CDCl3)7.56–7.59(m,0.9Hz,2H),7.31–7.34(m,3H),5.43(s,1H),0.16(s,9H).13C NMR(75MHz,CDCl3)136.1,128.8(x2),126.2(x2),119.1,63.5,-0.39(x3)。
二苯甲酮腙的缩合反应：
称取二苯甲酮腙1mmol放置于25mL小烧瓶中，再加入2mL无水甲醇及铵盐I0.15mmol，常温下搅拌24h后，取少量样品做核磁检测，转化率>99％；1H NMR(600MHz,CDCl3,27℃),δ 7.50–7.44(m,4H),7.43–7.36(m,6H),7.36–7.25(m,10H)。
Claims (4)
1.一种手性季铵盐化合物(I)的制备，其反应式如下：
2.由权利要求1所述的手性季铵盐化合物(I)，在293k温度下，在Oxford X-射线单晶衍射仪上，用经石墨单色器单色化的MoKa射线，λ＝0.71073A以w-Theta扫描方式收集衍射数据，其特征在于晶体属斜方晶系,空间群P21，晶胞参数：
α＝90°；
β＝98.303(5)°；
γ＝90°。
3.由权利要求1所述的手性季铵盐化合物的合成方法，包括合成和分离，其特征在于所述的合成用10mol％氯化锌做催化剂，首先加入无水ZnCl2 2mmol,50mL无水甲醇,氢氧化钠2.1639g,D-缬氨醇1.5656g,将混合物在高温下回流60h,停止反应,将粗产品用二氯甲烷及无水乙醇重结晶，得无色晶体。
4.权利要求1所述的手性季铵盐化合物(I)的用途，其特征在于其在苯甲醛的腈硅化反应及在二苯甲酮腙的缩合反应中显示了良好的催化性能，其转化率分别高达71％及99％。
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| CN109912427A (zh) * | 2019-04-06 | 2019-06-21 | 合肥祥晨化工有限公司 | 一种铵盐的制备及用途 |
| CN112300178A (zh) * | 2020-11-03 | 2021-02-02 | 合肥工业大学 | 一种5-溴喹唑啉衍生物的制备及用途 |
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| US20150344451A1 (en) * | 2011-02-14 | 2015-12-03 | Sogang University Research Foundation | Preparation method for an imine compound and reduction method for solid powder of a carbamic acid derivative |
| CN103992243A (zh) * | 2014-05-22 | 2014-08-20 | 罗梅 | 一种手性酰铵盐晶体的制备及用途 |
| CN109912427A (zh) * | 2019-04-06 | 2019-06-21 | 合肥祥晨化工有限公司 | 一种铵盐的制备及用途 |
| WO2020207129A1 (zh) * | 2019-04-06 | 2020-10-15 | 合肥祥晨化工有限公司 | 一种铵盐的制备及用途 |
| CN112300178A (zh) * | 2020-11-03 | 2021-02-02 | 合肥工业大学 | 一种5-溴喹唑啉衍生物的制备及用途 |
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