CN116987068A - 一种异香豆素-萘酚类联芳基化合物的制备方法 - Google Patents
一种异香豆素-萘酚类联芳基化合物的制备方法 Download PDFInfo
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- -1 isocoumarin-naphthol biaryl compound Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 9
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 229940125782 compound 2 Drugs 0.000 claims abstract description 7
- 239000010948 rhodium Substances 0.000 claims abstract description 7
- 229940125904 compound 1 Drugs 0.000 claims abstract description 6
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 229940126214 compound 3 Drugs 0.000 claims abstract description 4
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000005347 biaryls Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010596 desymmetrization reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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Abstract
本发明提供了一种异香豆素‑萘酚类联芳基化合物的制备方法，属于有机化学领域。以2‑(乙炔基吡啶)苯甲酸叔丁酯类化合物1和重氮萘醌类化合物2为原料，在铑催化剂和添加剂存在下，在有机溶剂中加热反应，得到异香豆素‑萘酚类联芳基化合物3。本发明方法一步反应即可完成，具有反应条件温和，反应路径合理，后处理简单，底物适用范围广等优点。
Description
技术领域
本发明属于有机合成领域，具体涉及一种异香豆素-萘酚类联芳基化合物的制备方法。
背景技术
联芳基化合物是手性配体、手性催化剂的核心骨架，广泛存在于天然产物、药物活性分子以及材料分子中。目前，化学家已经开发出多种方法来构建联芳基骨架(Nat.Chem.,2017,9,558)，例如过渡金属催化的交叉偶联、中心手性向轴手性的传递、联芳基化合物的去对称化及环加成等。
氧化偶联将两个C-H键转化成C-C键，为构建联芳基骨架提供了替代性策略，但是氧化偶联因底物自身固有的空间和电子特性，严重阻碍了其化学选择性、位点选择性和阻转选择性，并且该策略仅适用于富电子酚类底物，而缺电子酚的氧化偶联仍极具挑战性。
过渡金属催化的交叉偶联反应存在底物预官能团化、多步合成、条件严苛等问题而阻碍了反应的选择性和连接性，致使联芳基骨架的构建仍然是有机化学领域的一大难题。
因此开发新型、绿色和高效的合成结构多样的联芳基化合物的方法仍然具有重要的研究意义。
发明内容
为了解决上述技术问题，本发明提供了一种异香豆素-萘酚类联芳基化合物的制备方法。在铑催化剂和添加剂存在下，一步即可完成异香豆素-萘酚类联芳基化合物的合成，高效率得到异香豆素-萘酚类联芳基结构化合物。该方法具有如下优势：本发明可以通用，反应条件温和，反应时间短，成本低，反应路径合理，可高效制备该类型的化合物。
本发明提供了上述异香豆素-萘酚类联芳基化合物的合成方法，包括如下步骤：以2-(乙炔基吡啶)苯甲酸叔丁酯类化合物1和重氮萘醌类化合物2为原料，在铑催化剂和添加剂存在下，有机溶剂中加热反应，得到化合物3；反应方程式如下：
其中：R选自C1-C4烷基、芳基、卤素、酯基。
进一步地，在上述技术方案中，所述添加剂选自NaOAc。
进一步地，在上述技术方案中，所述化合物1、化合物2、铑催化剂与添加剂摩尔比为1.0:1.2-1.5:0.02-0.04:1.0。
进一步地，在上述技术方案中，有机溶剂选自六氟异丙醇。
进一步地，在上述技术方案中，所述加热反应温度为30-80℃。
进一步地，在上述技术方案中，反应无需惰性气体保护，可在空气中直接进行。
发明有益效果
本发明可高效率得到异香豆素-萘酚类联芳基化合物，本发明的优势在于：高效合成此类化合物，反应条件温和，底物适用范围广，反应路径合理，后处理简单。
具体实施方式
以下结合具体实施例对本发明的技术方案作进一步详细说明，但本发明的保护范围并不局限于此。
实施例1
条件优化实验
| Entry | Rh(x mol％) | Solvent | T/℃ | Yield |
| 1 | -- | HFIP | 40 | ND |
| 2 | 4％ | HFIP | 30 | 60％ |
| 3 | 4％ | TFE | 30 | ND |
| 4 | 4％ | DCE | 30 | ND |
| 5 | 4％ | EA | 30 | ND |
| 6 | 4％ | MeOH | 30 | ND |
| 7 | 4％ | HFIP | 40 | 75％ |
| 8 | 4％ | HFIP | 60 | 92％ |
| 9 | 4％ | HFIP | 80 | 99％ |
| 10 | 2％ | HFIP | 80 | 90％ |
Condition a:1(0.1mmol),2a(0.15mmol),[Cp*RhCl2]2(x mmol％),Additive(0.1mmol),T/℃,at air for 12h.
通过以上反应条件优化，最终确定最佳反应条件为：在六氟异丙醇中，采用[Cp*RhCl2]2为催化剂，在醋酸钠存在下反应。
实施例2：
采用化合物1与不同化合物2反应生成化合物3，典型合成步骤为：将化合物1a(0.1mmol,1.0eq)、[Cp*RhCl2]2(0.004mmol,0.04eq),化合物2(0.15mmol,1.5eq.)和NaOAc(0.1mmol,1.0eq.)混合，升温至80℃反应直至通过薄层板监测原料1完全消失(约12h)；旋干溶剂，柱层析分离(石油醚/乙酸乙酯体积比2:1)；反应结果如下：
典型化合物表征数据如下：
4-(2-hydroxynaphthalen-1-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3aa).Eluent:PE/EA＝(2:1),red-brown solid(41.2mg,99％,m.p.164-167℃).1H NMR(400MHz,DMSO-d6)δ9.70(s,1H),8.40(dt,J＝4.8,1.2Hz,1H),8.35-8.33(m,1H),7.87(d,J＝8.8Hz,1H),7.83-7.80(m,1H),7.69-7.61(m,2H),7.56(td,J＝8.0,2.0Hz,1H),7.40-7.38(m,1H),7.31(td,J＝8.0,1.2Hz,1H),7.27-7.17(m,4H),6.76-6.74(m,1H).13C NMR(100MHz,DMSO)δ161.5,153.7,150.9,150.5,149.2,138.2,136.2,135.3,133.6,130.2,129.0,129.0,128.2,127.9,126.9,125.2,123.9,123.7,123.1,122.9,120.8,118.4,112.1,112.0.
4-(7-bromo-2-hydroxynaphthalen-1-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3ab).Eluent:DCM/PE＝(2:1),black solid(38.5mg,87％,m.p.219-222℃).1H NMR(400MHz,DMSO-d6)δ9.81(s,1H),8.34(d,J＝6.8Hz,2H),8.09(d,J＝2.0Hz,1H),7.87(d,J＝8.8Hz,1H),7.70-7.59(m,3H),7.39-7.33(m,3H),7.27(d,J＝8.8Hz,1H),7.21-7.18(m,1H),6.75(d,J＝8.0Hz,1H).13C NMR(100MHz,DMSO)δ161.4,154.1,150.8,150.5,149.1,138.0,136.3,135.3,132.4,129.9,129.5,129.4,129.2,129.0,129.0,126.2,125.0,123.9,123.0,120.9,119.6,115.7,112.6,111.4.4-(2-hydroxy-7-isopropylnaphthalen-1-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3ac).Eluent:PE/EA＝(2:1),pale pinksolid(30.5mg,75％,m.p.203-205℃).1H NMR(400MHz,CDCl3)δ9.62(s,1H),8.43(dd,J＝8.0,1.6Hz,2H),7.81-7.71(m,4H),7.53-7.42(m,2H),7.33(d,J＝8.8Hz,1H),7.26(brs,1H),7.19(dd,J＝8.4,2.0Hz,1H),6.94(s,1H),6.60(d,J＝8.0Hz,1H),2.82-2.75(m,1H),1.06(t,J＝6.8Hz,6H).13C NMR(150MHz,CDCl3)δ162.0,154.5,147.4,138.7,137.8,135.1,134.1,130.3,129.6,129.1,128.4,128.0,126.8,123.0,121.6,121.1,120.8,115.8,113.0,34.3,24.1,23.7.
4-(2-hydroxy-7-phenylnaphthalen-1-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3ad).Eluent:PE/EA＝(2:1),dark brown solid(33.5mg,76％,m.p.228-230℃).1HNMR(600MHz,CDCl3)δ9.73(s,1H),8.44(d,J＝8.4Hz,2H),7.87(dd,J＝11.4,8.4Hz,2H),7.83(d,J＝7.8Hz,1H),7.75(t,J＝8.4Hz,1H),7.54-7.51(m,2H),7.47(t,J＝7.8Hz,1H),7.41(d,J＝9.0Hz,1H),7.35(d,J＝8.4Hz,3H),7.31-7.26(m,4H),6.65(d,J＝7.8Hz,1H).13C NMR(150 MHz,CDCl3)δ161.9,155.0,151.1,150.7,147.8,141.2,139.6,138.6,137.9,135.2,134.2,130.4,129.8,129.2,128.9,128.9,128.6,127.5,127.5,126.7,124.9,124.4,123.5,122.8,121.8,121.2,116.4,112.8.4-(7'-hydroxy-[1,2'-binaphthalen]-8'-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3ae).Eluent:PE/EA＝(2:1),whitesolid(38.2 mg,78％,m.p.140-142℃).1H NMR(400MHz,CDCl3)δ9.98(s,1H),8.45-8.37(m,2H),7.94(t,J＝9.2Hz,2H),7.84-7.74(m,4H),7.61-7.56(m,2H),7.49-7.22(m,8H),7.01(s,1H),6.74-6.72(m,1H).13C NMR(150MHz,CDCl3)δ161.6,155.2,151.1,150.5,147.7,139.9,138.9,138.8,137.9,135.1,133.9,133.8,131.4,130.4,129.9,129.1,128.6,128.5,128.4,127.9,127.2,126.8,126.2,126.0,125.9,125.4,125.4,125.0,124.5,122.1,121.3,116.5,112.8.4-(6-bromo-2-hydroxynaphthalen-1-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3af).Eluent:PE/EA＝(2:1),silvery solid(38 mg,86％,m.p.210-212℃).1H NMR(400MHz,CDCl3)δ9.69(s,1H),8.42-8.39(m,2H),7.93(d,J＝2.0Hz,1H),7.83-7.74(m,3H),7.54-7.40(m,3H),7.30-7.26(m,2H),7.07(d,J＝9.2Hz,1H),6.53(d,J＝7.6Hz,1H).13C NMR(150MHz,CDCl3)δ161.7,154.9,150.9,150.8,147.9,138.4,138.0,135.3,132.5,130.5,130.3,130.0,129.8,129.7,129.3,126.5,126.4,125.0,124.2,122.8,121.2,117.5,116.4,112.3.
Methyl 3-hydroxy-4-(1-oxo-3-(pyridin-2-yl)-1H-isochromen-4-yl)-2-naphthoate(3ag).Eluent:PE/EA＝(2:1),yellow solid(22.5mg,53％,m.p.290-290℃).1H NMR(400MHz,CDCl3)δ10.70(s,1H),8.62(s,1H),8.48-8.45(m,1H),8.23(d,J＝4.8Hz,1H),7.85(d,J＝8.0Hz,1H),7.59(dt,J＝8.0,1.2Hz,1H),7.55-7.52(m,2H),7.49-7.44(m,2H),7.38-7.34(m,1H),7.32-7.28(m,1H),7.02-6.98(m,1H),6.90-6.86(m,1H),4.05(s,3H).13C NMR(150MHz,CDCl3)δ170.5,162.1,154.6,151.3,150.7,149.3,138.3,137.2,136.0,135.0,133.3,130.0,129.9,129.9,128.8,127.1,125.4,124.3,124.2,123.5,123.1,121.4,115.9,113.9,111.8,52.9.
4-(2-hydroxy-1-methyl-2,7a-dihydro-1H-indol-3-yl)-3-(pyridin-2-yl)-1H-isochromen-1-one(3ah).Eluent:PE/EA＝(3:1),light yellow solid(34.6mg,93％,m.p.177-179℃).1H NMR(400MHz,DMSO-d6)δ8.68(dt,J＝4.4,1.6Hz,1H),8.25(dd,J＝8.0,1.6Hz,1H),8.09-8.07(m,2H),7.64(td,J＝7.6,1.6Hz,1H),7.60-7.53(m,2H),7.36(t,J＝7.6Hz,1H),7.24(d,J＝7.2Hz,1H),7.19(d,J＝7.6Hz,1H),7.00(t,J＝7.6Hz,1H),6.58(d,J＝7.6Hz,1H),6.49(s,1H),3.29(s,3H),3.14(s,1H).13C NMR(100MHz,DMSO)δ174.8,160.3,151.8,150.9,149.1,143.3,137.9,136.1,135.5,129.6,129.2,128.4,127.9,124.9,124.2,123.6,123.5,122.5,120.9,110.8,109.1,44.9,26.5.
上述产物在NaH(1.0eq)/PPh2Cl(1.1eq)/0℃/THF或n-BuLi(1.0eq)/PPh2Cl(1.1eq)/0℃/THF可制备成N,P配体，用于催化反应。
以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。
Claims (6)
1.一种异香豆素-萘酚类联芳基化合物的制备方法，其特征在于，包括如下步骤：以2-(乙炔基吡啶)苯甲酸叔丁酯类化合物1和重氮萘醌类化合物2为原料，在铑催化剂和添加剂存在下，有机溶剂中加热反应，得到化合物3；反应方程式如下：
其中：R选自C1-C4烷基、芳基、卤素。
2.根据权利要求1所述异香豆素-萘酚类联芳基化合物的制备方法，其特征在于：所述添加剂选自NaOAc。
3.根据权利要求1所述异香豆素-萘酚类联芳基化合物的制备方法，其特征在于：所述化合物1、化合物2、铑催化剂与添加剂摩尔比为1.0:1.2-1.5:0.04:1.0。
4.根据权利要求1所述异香豆素-萘酚类联芳基化合物的制备方法，其特征在于：有机溶剂为六氟异丙醇。
5.根据权利要求1所述异香豆素-萘酚类联芳基化合物的制备方法，其特征在于：所述加热反应温度为30-80℃。
6.根据权利要求1-5任意一项所述异香豆素-萘酚类联芳基化合物的制备方法，其特征在于：反应在空气中进行。
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