CN111704587B - 一种三氟甲基化1,3-噁嗪类化合物的合成方法 - Google Patents
一种三氟甲基化1,3-噁嗪类化合物的合成方法 Download PDFInfo
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- -1 trifluoromethyl 1, 3-oxazine compound Chemical class 0.000 title claims abstract description 50
- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 150000001879 copper Chemical class 0.000 claims abstract description 15
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- KAVUKAXLXGRUCD-UHFFFAOYSA-M sodium trifluoromethanesulfinate Chemical compound [Na+].[O-]S(=O)C(F)(F)F KAVUKAXLXGRUCD-UHFFFAOYSA-M 0.000 claims abstract description 6
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical group [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical group [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 6
- 229940071536 silver acetate Drugs 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000003814 drug Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical group [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000004895 1,3-oxazines Chemical class 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- XOZIUKBZLSUILX-SDMHVBBESA-N Epothilone D Natural products O=C1[C@H](C)[C@@H](O)[C@@H](C)CCC/C(/C)=C/C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C XOZIUKBZLSUILX-SDMHVBBESA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical group [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- XOZIUKBZLSUILX-UHFFFAOYSA-N desoxyepothilone B Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC(C)=CCC1C(C)=CC1=CSC(C)=N1 XOZIUKBZLSUILX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XOZIUKBZLSUILX-GIQCAXHBSA-N epothilone D Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC\C(C)=C/C[C@H]1C(\C)=C\C1=CSC(C)=N1 XOZIUKBZLSUILX-GIQCAXHBSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002697 lyase inhibitor Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- SFEBPWPPVGRFOA-UHFFFAOYSA-N trifluoromethanesulfinic acid Chemical compound OS(=O)C(F)(F)F SFEBPWPPVGRFOA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
一种三氟甲基化1,3‑噁嗪类化合物的合成方法,包括以下步骤：1)选芳甲酰亚胺高烯丙酯、三氟甲基亚磺酸钠、银盐和铜盐依次加入到有机溶剂中；2)加热至适合温度制得三氟甲基取代的1,3‑噁嗪类化合物。本发明以芳甲酰亚胺高烯丙酯为底物，使用廉价的三氟甲基亚磺酸钠为三氟甲基试剂，在铜盐和银盐的作用下，合成三氟甲基取代的1,3‑噁嗪类化合物，为该类化合物提供一条经济的合成路线。
Description
技术领域
本发明涉及一种三氟甲基化1,3-噁嗪类化合物的合成方法，属于属于有机合成技术领域。
背景技术
三氟甲基是一类比较特殊的含氟基团，该结构中含有三个碳氟(C-F)键，使其拥有很多含氟原子的性质。利用三氟甲基的特殊性质，将三氟甲基引入到活性药物分子中，通过改变母体分子的偶极矩、酸性、亲脂性、极性和化学稳定性，可以显著增强母体药物分子的代谢稳定性和脂溶性，并能影响药物在体内的吸收、分布以及与靶点的相互作用等。如将具有较好市场前景的肿瘤抑制剂埃博霉素D的C12、C13位的甲基改换成三氟甲基后，药物分子的稳定性增强，药物作用时间延长，毒副作用减少。鉴于1,3-噁嗪是一些β-淀粉样前体蛋白裂解酶抑制剂的核心骨架结构，把拥有特殊性质的三氟甲基引入该类分子中，将有助于开发新型生物活性分子。该类化合物已有的合成方法中，使用比较昂贵的3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环)为三氟甲基源(Org Lett 2019,21,4657)，反应原子经济性差，局限了该类分子的工业应用。
发明内容
本发明所要解决的是使用廉价的三氟甲基亚磺酸钠为三氟甲基试剂，在铜盐和银盐的作用下，合成三氟甲基取代的1,3-噁嗪类化合物，为该类化合物提供一条经济的合成路线的技术问题。
为了解决上述技术问题，本发明采用如下技术方案：
一种三氟甲基化1,3-噁嗪类化合物的合成方法,包括以下步骤：1)选芳甲酰亚胺高烯丙酯、三氟甲基亚磺酸钠、银盐和铜盐依次加入到有机溶剂中；
2)加热至适合温度制得三氟甲基取代的1,3-噁嗪类化合物，见以下化学反应式如下：
上述各式中：
Ar为苯基、邻甲基苯基、间甲基苯基、对甲基苯基、间乙基苯基、对乙基苯基、对氯苯基、间氯苯基、邻氯苯基、邻溴苯基、间溴苯基、对溴苯基，间氟苯基、对氟苯基、间叔丁基苯基、对叔丁基苯基、萘基、3,5-二甲基苯基、对甲氧基苯基、间甲氧基苯基、3,4,5-三甲氧基苯基、间三氟甲基苯基、对三氟甲基苯基中的一个或多个所取代。
所述铜盐选自乙酰丙酮酸铜、醋酸铜、三氟甲烷磺酸铜、溴化铜、氯化铜。
所述铜盐优选醋酸铜。
所述银盐选自氧化银、三氟甲烷磺酸银、醋酸银、硫酸银、溴化银、氯化银、碘化银、硝酸银。
所述银盐优选醋酸银。
所述有机溶剂选自二氯乙烷、乙酸乙酯、1,2-二氯乙烷、四氢呋喃、乙腈、N,N-二甲基甲酰胺、二甲基亚砜、正己烷、正庚烷、环己烷。所述有机溶剂优选乙腈。
所述加热的适当温度为40-100℃，维持时间为1-60小时。
所述加热的适当温度优选80℃，维持时间为24小时。
所述芳甲酰亚胺高烯丙酯：三氟甲基亚磺酸钠：铜盐：银盐摩尔量比为：1：1～5：0.01～0.5：1～3。
所述芳甲酰亚胺高烯丙酯：三氟甲基亚磺酸钠：铜盐：银盐摩尔量比优选为1：2：0.2：2。
采用上述技术方案的有益效果是：
本发明以芳甲酰亚胺高烯丙酯为底物，使用廉价的三氟甲基亚磺酸钠为三氟甲基试剂，在铜盐和银盐的作用下，合成三氟甲基取代的1,3-噁嗪类化合物，为该类化合物提供一条经济的合成路线。
具体实施方式
以下通过具体实施例对本发明做进一步的说明，但不应该将此理解为本发明上述主题的范围仅限于以下的实施例，凡基于本发明上述内容实现的技术均属于本发明的范围。
实施例一：
一种三氟甲基化1,3-噁嗪类化合物的合成方法,包括以下步骤：1)以对甲基苯甲酰亚胺高烯丙酯为底物、三氟甲基亚磺酸钠为三氟甲基试剂、醋酸铜为铜盐、醋酸银为银盐、乙腈为反应溶剂；
2)将对甲基苯甲酰亚胺高烯丙酯(37.8mg，0.2mmol)，三氟甲基亚磺酸钠(62.4mg,0.4mmol)，醋酸银(66.8mg,0.4mmol)，醋酸铜(7.2mg,0.04mmol)依次加入到搅拌的乙腈(2mL)中，在80℃下反应24小时，后经萃取、干燥、浓缩和硅胶柱层析得到无色液体(18.2mg,71％)，化学反应式1为：
产物检测数据如下：
1H NMR(400MHz,CDCl3)δ7.78(d,J＝8.3Hz,2H),7.16(d,J＝8.0Hz,2H),4.49–4.36(m,1H),4.34–4.21(m,1H),3.92–3.81(m,1H),2.76–2.65(m,1H),2.38(s,3H),2.25–2.14(m,2H),1.82–1.75(m,1H)；13C NMR(101MHz,CDCl3)δ155.7,140.8,130.9,128.9,127.3,125.2,64.0,47.1,41.7(q,J＝27.2Hz),27.6,21.7；19F NMR(376MHz,CDCl3)δ-63.40(t,J＝10.6Hz,3F)。
实施例二：
一种三氟甲基化1,3-噁嗪类化合物的合成方法,包括以下步骤：1)以对甲基苯甲酰亚胺高烯丙酯为底物、苯甲酸银为羧基试剂、醋酸铜为铜盐、乙腈为反应溶剂；
2)将对甲基苯甲酰亚胺高烯丙酯(44.5mg，0.2mmol)，三氟甲基亚磺酸钠(62.4mg,0.4mmol)，醋酸银(66.8mg,0.4mmol)，醋酸铜(7.2mg,0.04mmol)依次加入到搅拌的乙腈(2mL)中，在80℃下反应24小时，后经萃取、干燥、浓缩和硅胶柱层析得到无色液体(37.5mg,64％)，化学反应式2为：
产物检测数据如下：
1H NMR(400MHz,CDCl3)δ8.40(s,1H),8.04(d,J＝8.6Hz,1H),7.93–7.89(m,1H),7.85(t,J＝7.1Hz,2H),7.57–7.44(m,2H),4.56–4.43(m,1H),4.41–4.34(m,1H),4.03–3.92(m,1H),2.89–2.66(m,1H),2.37–2.24(m,2H),1.96–1.79(m,1H)；13C NMR(101MHz,CDCl3)δ155.7,134.8,132.9,131.1,129.1,127.7,127.9,127.3,127.2,126.5,124.4,64.3,47.3,41.8(q,J＝27.0Hz),27.4；19F NMR(376MHz,CDCl3)δ-63.40(t,J＝11.1Hz,3F)。
Claims (5)
1.一种三氟甲基化1,3-噁嗪类化合物的合成方法, 其特征在于：它包括以下步骤：1）选芳甲酰亚胺高烯丙酯、三氟甲基亚磺酸钠、银盐和铜盐依次加入到有机溶剂中；2）加热至适合温度制得三氟甲基取代的1,3-噁嗪类化合物，化学反应式如下：
,
上述各式中：
Ar为苯基、邻甲基苯基、间甲基苯基、对甲基苯基、间乙基苯基、对乙基苯基、对氯苯基、间氯苯基、邻氯苯基、邻溴苯基、间溴苯基、对溴苯基，间氟苯基、对氟苯基、间叔丁基苯基、对叔丁基苯基、萘基、3,5-二甲基苯基、对甲氧基苯基、间甲氧基苯基、3,4,5-三甲氧基苯基、间三氟甲基苯基或对三氟甲基苯基；
所述铜盐选自醋酸铜；
所述银盐选自醋酸银；
所述有机溶剂选自二氯乙烷、乙酸乙酯、1,2-二氯乙烷、四氢呋喃、乙腈、N,N-二甲基甲酰胺、二甲基亚砜、正己烷、正庚烷、环己烷；
所述适合温度为40～100 ℃，维持时间为1～60小时。
2.根据权利要求1所述三氟甲基化1,3-噁嗪类化合物的合成方法, 其特征在于：所述有机溶剂选自乙腈。
3.根据权利要求1所述三氟甲基化1,3-噁嗪类化合物的合成方法, 其特征在于：所述适合温度为80 ℃，维持时间为24 小时。
4.根据权利要求1所述三氟甲基化1,3-噁嗪类化合物的合成方法, 其特征在于：所述芳甲酰亚胺高烯丙酯：三氟甲基亚磺酸钠：铜盐：银盐摩尔量比为： 1：1～5：0.01～0.5：1～3。
5.根据权利要求1或4所述三氟甲基化1,3-噁嗪类化合物的合成方法, 其特征在于：所述芳甲酰亚胺高烯丙酯：三氟甲基亚磺酸钠：铜盐：银盐摩尔量比为 1：2：0.2：2。
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