CN115583876A - 苯基萘嵌苯酮化合物及其制备方法和应用 - Google Patents
苯基萘嵌苯酮化合物及其制备方法和应用 Download PDFInfo
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- CN115583876A CN115583876A CN202110759940.9A CN202110759940A CN115583876A CN 115583876 A CN115583876 A CN 115583876A CN 202110759940 A CN202110759940 A CN 202110759940A CN 115583876 A CN115583876 A CN 115583876A
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- nmr
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- compound
- 400mhz
- phenalen
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- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- PFGVNLZDWRZPJW-OPAMFIHVSA-N otamixaban Chemical compound C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C=1C=C[N+]([O-])=CC=1)C1=CC=CC(C(N)=N)=C1 PFGVNLZDWRZPJW-OPAMFIHVSA-N 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DPZNOMCNRMUKPS-UHFFFAOYSA-N resorcinol dimethyl ether Natural products COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及医药技术领域，涉及苯基萘嵌苯酮化合物及其制备方法和应用，具体涉及苯基萘嵌苯酮化合物及其制备方法和在制备抗病毒或抗肿瘤药物中的应用。本发明所述的苯基萘嵌苯酮化合物或其药学上可接受的盐如通式I或II所示，其中所述R1和Ar如权利要求和说明书所述。
Description
技术领域
本发明涉及医药技术领域，涉及苯基萘嵌苯酮化合物及其制备方法和应用，具体涉及苯基萘嵌苯酮化合物及其制备方法和在制备抗病毒、抗肿瘤药物中的应用。
背景技术
苯基萘嵌苯酮类化合物是一类天然的植物类毒素，主要在芭蕉科、雨久花科植物中分布。当此类植物收到病虫害入侵时，植物体自身会产生和分泌此类化合物，从而达到保护植物体自身的目的。鉴于天然来源的苯基萘嵌苯酮类化合物在植物体内含量较低，且分离纯化困难，不利于科研人员研究及应用开发。
目前对于苯基萘嵌苯酮类化合物仅限于对某些化合物的合成研究，而且合成方法只能针对单一化合物制备，并没有一种通用的方法可以合成各种不同取代条件的化合物。且也未见此类化合物在制备抗病毒、抗肿瘤药物方面的应用的相关报道。
发明内容
本发明所解决的技术问题是为了克服现有技术的缺陷，提供一系列新的苯基萘嵌苯酮化合物，所述的苯基萘嵌苯酮化合物具有明显的抗病毒、抗肿瘤活性。
本发明是通过如下技术实现的：
本发明提供通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基；
Ar为取代或未取代的6-10元芳基或5-10元杂芳基，所述取代基为C1-C6烷基、硝基、氨基、羟基、氰基、C1-C6烷氧基中的一个或多个，或所述芳基或杂芳基的相邻位置的取代基一起组成5-6元杂环基，所述杂环基含有1-3个N、O或S的杂原子。
本发明优选通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基；
Ar为取代或未取代的苯基，所述取代基为C1-C4烷基、硝基、氨基、羟基、氰基、C1-C4烷氧基中的一个或多个，或所述苯基的相邻位置的取代基一起组成5-6元杂环基，所述杂环基含有1-3个O原子；
本发明优选通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基；
Ar为取代或未取代的苯基，所述取代基为C1-C4烷基、硝基、C1-C4烷氧基中的一个或多个，或与萘嵌苯酮连接的苯基的对位和邻位一起组成5-6元杂环基，所述杂环基含有1-3个O原子；
本发明优选通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基；
Ar为
取代或未取代的苯基，所述取代基为C1-C4烷基、硝基、C1-C4烷氧基中的一个或多个；
本发明优选通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基；
本发明优选如下苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
表1本发明的具体化合物
进一步地，本发明提供了所述的苯基萘嵌苯酮化合物的制备方法，
其中，
R为卤素；Ar如权利要求所述；
所述制备方法包括如下步骤：
(1)萘嵌苯酮III-1或III-2与不同的硼酸酯经过铃木偶联反应得到化合物A或D；
(2)化合物A或D经过过氧叔丁醇环氧化及开环反应得到化合物B或E；
(3)化合物B或E与碘甲烷在碱性作用下反应得到化合物C或F。
其中，
步骤(1)中所述的铃木偶联反应中，所用的碱为碳酸钾，催化剂为醋酸钯，所述的硼酸酯为芳基硼酸酯；
步骤(2)中使用的碱为苄基三甲基氢氧化铵、催化剂为对甲苯磺酸。
步骤(3)所述的反应中，所述的碱为碳酸钾，溶剂为N,N-二甲基甲酰胺(DMF)。
或所述制备方法包括如下步骤：
本发明提供一种药物组合物，包含通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐和药学上可接受的载体或赋形剂。
本发明进一步提供了通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐在制备抗病毒药物中的应用。
所述的病毒为烟草花叶病毒。
本发明还提供了通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐在制备抗肿瘤药物中的应用。
所述的肿瘤为结肠癌、胰腺癌、前列腺癌、乳腺癌、乳腺管癌。
具体实施方式
以下结合具体实施例来进一步说明本发明，但实施例并不对本发明做任何形式的限定。除非特别说明，本发明采用的试剂、方法和设备为本技术领域常规试剂、方法和设备。
其中，本实施例中采用的试剂和仪器信息如下：
试剂:萘嵌苯酮、4-溴-萘嵌苯酮、5-溴-萘嵌苯酮、6-溴-萘嵌苯酮、7-溴-萘嵌苯酮、8-溴-萘嵌苯酮、取代的芳基硼酸酯、四三苯基膦钯、过氧叔丁醇、对甲苯磺酸、氢氧化三甲基苄铵、THF、碳酸钾、甲醇、石油醚、乙酸乙酯、二氯甲烷等。
仪器:ABI Maldi-TOF和Qstar Elite高分辨质谱系统；BrukerAvance 400MHz核磁共振波谱仪(瑞士Bruker公司)；Agilent GC-MS；EYLA(SB-1200)旋转蒸发仪(上海爱朗仪器有限公司)；
C-MAG HS 7磁力搅拌器(上海爱朗仪器有限公司)；YUHUA(ZF-20DAN)暗箱式紫外分析仪(上海光豪分析仪器有限公司)；KQ5200E型超声清洗器(昆山市超声仪器有限公司)，SB-1200水浴锅(上海爱朗仪器有限公司)，A-1000S水流抽气机(上海爱朗仪器有限公司)。
实施例1：目标化合物4a-g,5a-g,6a-g,7a-g,8a-g,9a-f的合成(以4a为例)
在一个100毫升的三口瓶中加入5-溴-萘嵌苯酮(4,80.0mg,0.31mmol),Pd(PPh3)4(160.0mg,0.13mmol)和THF(10.0mL)。在氮气保护下搅拌15分钟，然后加入苯硼酸溶液(55.0mg,0.45mmol，溶解在10.0mL THF)，接着加入1.0mL Na2CO3(1M,aq.)溶液，反应液加热回流3个小时，蒸干溶剂，然后加入100.0mL CH2Cl2/H2O2(1:1)萃取，有机层合并浓缩，经硅胶柱分离纯化得到目标化合物4a(60mg,75.0％),洗脱剂为(石油醚/乙酸乙酯＝9:1)。按照该方法分别制备如下化合物，其中化合物9a-f参考已知方法合成，化合物理化数据如下：
4-Phenyl-1H-phenalen-1-one(化合物4a):
Orange solid,mp 148-150℃.1H-NMR(400MHz,CDCl3)δ8.68(dd,J＝7.6,1.2Hz,1H,Ar-H),8.19(d,J＝7.2Hz,1H,Ar-H),8.03(d,J＝8.4Hz,1H,Ar-H),7.84(d,J＝10.0Hz,1H,-CH＝CH-),7.76(t,J＝7.6Hz,1H,Ar-H),7.57(d,J＝8.4Hz,1H,Ar-H),7.44-7.52(m,5H,Phenly-H),6.67(d,J＝10.0Hz,1H,-CH＝CH-).13C-NMR(100MHz,CDCl3)δ185.3,144.9,139.9,139.1,134.9,131.7,131.5,130.8,130.3(2C),129.7,129.3,128.8,128.4(2C),128.2,127.9,126.9,124.4.HRMS(ESI)calcd.for[C19H12O+Na]+279.0780,found 279.0785.
4-(4-Methoxyphenyl)-1H-phenalen-1-one(化合物4b):
Orange solid,mp 164-166℃.1H-NMR(400MHz,CDCl3)δ8.63(d,J＝7.2Hz,1H,Ar-H),8.13(d,J＝8.0Hz,1H,Ar-H),7.96(d,J＝8.4Hz,1H,Ar-H),7.85(d,J＝10.0Hz,1H,-CH＝CH-),7.71(dt,J＝8.0,7.6Hz,1H,Ar-H),7.53(d,J＝8.4Hz,1H,Ar-H),7.36(d,J＝8.4Hz,2H,Ar-H),7.04(d,J＝8.8Hz,2H,Ar-H),6.65(d,J＝10.0Hz,1H,-CH＝CH-),3.88(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ185.2,159.7,144.7,140.0,134.8,131.8,131.7(3C),131.3,130.6,129.6,129.4,128.5,128.0,126.7,124.2,114.0(2C),55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1075.
4-(2,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物4c):
Orange solid,mp 177-179℃.1H-NMR(400MHz,CDCl3)δ8.65(d,J＝7.2Hz,1H,Ar-H),8.17(d,J＝8.0Hz,1H,Ar-H),7.99(d,J＝8.4Hz,1H,Ar-H),7.68-7.76(m,1H,Ar-H；1H,-CH＝CH-),7.54(d,J＝8.4Hz,1H,Ar-H),7.17(d,J＝8.8Hz,1H,Ar-H),6.64-6.67(m,2H,Ar-H；1H,-CH＝CH-),3.91(s,3H,-OCH3),3.76(s,3H,-OCH3)Ar-H.13C-NMR(100MHz,CDCl3)δ185.6,161.4,157.8,141.8,140.6,134.8,132.8,131.5,131.1,130.4(2C),129.6,128.2,127.9,126.6,125.4,120.3,104.6,98.9,55.5(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1180.
4-(3,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物4d):
Orange solid,mp 184-186℃.1H-NMR(400MHz,CDCl3)δ8.66(d,J＝7.2Hz,1H,Ar-H),8.19(d,J＝8.0Hz,1H,Ar-H),8.02(d,J＝8.4Hz,1H,Ar-H),7.90(d,J＝10.0Hz,1H,-CH＝CH-),7.76(t,J＝7.6Hz,1H,Ar-H),7.59(d,J＝8.4Hz,1H,Ar-H),6.99-7.02(m,3H,Ar-H),6.68(d,J＝10.0Hz,1H,-CH＝CH-),3.98(s,3H,-OCH3),3.94(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ185.3,149.2,148.8,144.8,140.0,134.8,131.6,131.6,131.3,130.7,129.6,129.3,128.6,128.0,126.8,124.3,123.2,113.4,111.0,56.1,56.0.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1169.
4-(Benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物4e):
Orange solid,mp 159-161℃.1H-NMR(400MHz,CDCl3)δ8.67(d,J＝7.2Hz,1H,Ar-H),8.18(d,J＝7.6Hz,1H,Ar-H),8.01(d,J＝8.4Hz,1H,Ar-H),7.90(d,J＝10.0Hz,1H,-CH＝CH-),7.76(t,J＝7.6Hz,1H,Ar-H),7.55(d,J＝8.4Hz,1H,Ar-H),6.95-6.98(m,2H,Ar-H),6.90(d,J＝8.0Hz,1H,Ar-H),6.69(d,J＝10.0Hz,1H,-CH＝CH-),6.08(s,2H,-OCH2-).13C-NMR(100MHz,CDCl3)δ185.2,147.8(2C),144.5,139.8,134.8,132.8,131.6,131.4,130.7,129.6,129.3,128.7,128.0,126.8,124.4,124.3,110.6,108.3,101.5.HRMS(ESI)calcd.for[C20H12O3+H]+301.0859,found 301.0859.
4-(3,4,5-Trimethoxyphenyl)-1H-phenalen-1-one(化合物4f):
Orange solid,mp 184-186℃.1H-NMR(400MHz,CDCl3)δ8.66(d,J＝8.0Hz,1H,Ar-H),8.21(d,J＝8.0Hz,1H,Ar-H),8.04(d,J＝8.0Hz,1H,Ar-H),7.91(d,J＝8.0Hz,1H,-CH＝CH-),7.78(t,J＝8.0Hz,1H,Ar-H),7.60(d,J＝8.0Hz,1H,Ar-H),6.69(d,J＝8.0Hz,1H,-CH＝CH-),6.65(s,2H,Ar-H),3.95(s,3H,-OCH3),3.91(s,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ185.6,153.2(2C),144.8,139.9,138.1,134.9,134.7,131.6,131.5,130.9,129.7,129.1,128.8,127.9,127.0,124.5,107.6(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found347.1276.
4-(3-Nitrophenyl)-1H-phenalen-1-one(化合物4g):
Orange solid,mp 202-204℃.1H-NMR(400MHz,CDCl3)δ8.55(brs,1H,Ar-H),8.25(brs,1H,Ar-H；1H,-CH＝CH-),8.13(brs,1H,Ar-H),8.00(brs,1H,Ar-H),7.58-7.71(m,4H,Ar-H),7.47(s,1H,Ar-H),6.58(brs,1H,-CH＝CH-).13C-NMR(100MHz,CDCl3)δ184.8,148.2,141.6,140.7,138.4,136.3,135.0,132.0,131.8,131.1,129.8,129.7,129.6,128.6,127.8,127.4,124.8,124.7,123.0.HRMS(ESI)calcd.for[C19H11NO3+Na]+324.0631,found324.0630.
5-Phenyl-1H-phenalen-1-one(化合物5a):
Orange solid,mp:145-147℃.1H NMR(400MHz,CDCl3)δ8.58(dd,J＝7.3,1.1Hz,1H),8.21(dd,J＝8.1,0.8Hz,1H),8.15(d,J＝1.6Hz,1H),7.95(d,J＝1.6Hz,1H),7.79–7.74(m,2H),7.73–7.69(m,2H),7.55–7.49(m,2H),7.47–7.41(m,1H),6.75(d,J＝9.7Hz,1H).13C NMR(100MHz,CDCl3)δ185.7,141.7,139.7,135.0,132.6,131.0,130.1,129.6,129.4,129.3,129.2,128.3,128.1,127.5,127.3,126.7.HRMS(ESI)calcd.for[C19H12O+Na]+279.0780,found279.0785.
5-(4-Methoxyphenyl)-1H-phenalen-1-one(化合物5b):
Orange solid,mp:160-162℃.1H NMR(400MHz,CDCl3)δ8.58(dd,J＝7.3,0.9Hz,1H),8.21(d,J＝7.6Hz,1H),8.13(d,J＝1.5Hz,1H),7.96(d,J＝1.5Hz,1H),7.78(dd,J＝12.7,5.5Hz,2H),7.69–7.63(m,2H),7.06(dd,J＝6.9,4.9Hz,2H),6.76(d,J＝9.7Hz,1H),3.89(s,3H).13C NMR(100MHz,CDCl3)δ185.7,159.8,141.8,139.3,134.9,132.7,132.2,130.9,129.8,129.6,129.4,128.6,128.4,128.3,127.5,126.5,114.6,55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1075.
5-(2,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物5c):
Orange solid,mp:176-178℃.1H NMR(400MHz,CDCl3)δ8.60(dd,J＝7.4,1.1Hz,1H),8.21(dd,J＝8.1,0.8Hz,1H),8.09(d,J＝1.5Hz,1H),7.96(d,J＝1.5Hz,1H),7.81–7.74(m,2H),7.36(t,J＝5.3Hz,1H),6.78–6.73(m,1H),6.65(d,J＝2.4Hz,1H),6.62(d,J＝2.1Hz,1H),3.89(s,3H),3.85(s,3H).13C NMR(100MHz,CDCl3)δ185.9,161.0,157.6,142.2,137.2,135.0,134.0,132.5,131.6,131.4,129.9,129.4,129.2,127.3,127.2,126.4,122.0,105.0,99.1,55.7,55.5.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1180.
5-(3,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物5d):
Orange solid,mp:181-183℃.1H NMR(400MHz,CDCl3)δ8.57(dd,J＝7.3,0.9Hz,1H),8.22(d,J＝7.6Hz,1H),8.12(d,J＝1.4Hz,1H),7.95(d,J＝1.4Hz,1H),7.81–7.73(m,2H),7.27(dd,J＝8.3,2.1Hz,1H),7.22(d,J＝2.0Hz,1H),7.01(d,J＝8.3Hz,1H),6.75(d,J＝9.7Hz,1H),4.01(s,3H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ185.7,149.5,149.3,141.7,139.5,134.9,132.6,130.9,129.9,129.6,129.3,128.7,128.3,127.5,126.5,119.8,111.7,110.5,56.1,56.1.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1169.
5-(Benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物5e):
Orange solid,mp:163-165℃.1H NMR(400MHz,CDCl3)δ8.58(dd,J＝7.3,0.9Hz,1H),8.21(d,J＝8.0Hz,1H),8.09(d,J＝1.4Hz,1H),7.91(d,J＝1.4Hz,1H),7.82–7.73(m,2H),7.21–7.15(m,2H),6.98–6.92(m,1H),6.75(d,J＝9.7Hz,1H),6.05(s,2H).13C NMR(100MHz,CDCl3)δ185.7,148.5,147.8,141.6,139.4,134.9,134.0,132.6,130.8,129.9,129.6,129.4,128.8,128.3,127.5,126.6,121.0,108.9,107.7,101.4.HRMS(ESI)calcd.for[C20H12O3+H]+301.0859,found 301.0859.
5-(3,4,5-Trimethoxyphenyl)-1H-phenalen-1-one(化合物5f):
Orange solid,mp:178-180℃.1H NMR(400MHz,CDCl3)δ8.60(d,J＝7.2Hz,1H),8.25(d,J＝8.0Hz,1H),8.14(d,J＝0.9Hz,1H),7.95(s,1H),7.80(dd,J＝8.3,8.0Hz,2H),6.91(s,2H),6.77(d,J＝9.8Hz,1H),3.99(s,6H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ185.6,153.8,141.6,139.9,138.5,135.7,134.9,132.5,130.9,130.1,129.7,129.4,129.1,128.4,127.6,126.7,104.8,61.0,56.4.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1276.
5-(3-Nitrophenyl)-1H-phenalen-1-one(化合物5g):
Orange solid,mp:197-199℃.1H NMR(400MHz,CDCl3)δ8.70–8.57(m,2H),8.34–8.22(m,3H),8.08(d,J＝7.5Hz,1H),8.01(s,1H),7.84(dd,J＝13.0,5.8Hz,2H),7.72(t,J＝7.9Hz,1H),6.81(d,J＝9.7Hz,1H).13C NMR(100MHz,CDCl3)δ185.5,141.5,141.4,137.1,135.2,133.2,132.5,130.9,130.2,130.1,130.0,129.8,129.4,129.0,128.0,122.9,122.2.HRMS(ESI)calcd.for[C19H11NO3+Na]+324.0631,found 324.0630.
6-Phenyl-1H-phenalen-1-one(化合物6a):
Orange solid,mp 141–143℃.1H-NMR(400MHz,CDCl3)δ8.59(d,J＝7.2Hz,1H),8.21(d,J＝8.4Hz,1H),7.63-7.70(m,3H),7.45-7.49(m,6H),6.70(d,J＝9.6Hz,1H).13C-NMR(100MHz,CDCl3)δ185.8,144.9,141.8,139.3,133.6,131.1,130.7,130.4,130.2(2C),129.7,128.9,128.5(2C),128.1,127.9,127.6,127.1,127.0.HRMS(ESI)calcd.for[C19H12O+Na]+279.0780,found 279.0782.
6-(4-methoxyphenyl)-1H-phenalen-1-one(化合物6b):
Orange solid,mp 148-150℃.1H-NMR(400MHz,CDCl3)δ8.62(d,J＝7.2Hz,1H),8.27(d,J＝8.4Hz,1H),7.67-7.73(m,3H),7.48(d,J＝7.2Hz,1H),7.41(d,J＝8.0Hz,2H),7.05(d,J＝8.4Hz,2H),6.72(d,J＝9.6Hz,1H),3.89(s,3H).13C-NMR(100MHz,CDCl3)δ185.7,159.6,144.6,141.8,133.7,131.6,131.3(2C),131.2,130.8,130.3,129.7,128.6,127.9,127.4,126.9,126.7,114.0(2C),55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1075.
6-(2,4-dimethoxyphenyl)-1H-phenalen-1-one(化合物6c):
Orange solid,mp 148-150℃.1H-NMR(400MHz,DMSO-d6)δ8.45(d,J＝5.6Hz,1H),8.02(m,2H),7.95(d,J＝8.0Hz,1H),7.79(dt,J＝7.2Hz,6.8Hz,1H),7.53(d,J＝5.6Hz,1H),7.21(d,J＝8.0Hz,1H),6.70-6.77(m,2H),6.68(d,J＝10.0Hz,1H),3.86(s,3H),3.65(s,3H).13C-NMR(100MHz,DMSO-d6)δ184.4,160.9,157.5,142.3,141.5,133.7,131.9,131.8,130.9,129.4,128.9,128.6,127.9,127.0,126.8,126.3,119.7,105.2,98.7,55.3,55.3.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1165.
6-(3,4-dimethoxyphenyl)-1H-phenalen-1-one(化合物6d):
Orange solid,mp 148-150℃.1H-NMR(400MHz,CDCl3)δ8.63(d,J＝7.2Hz,1H),8.31(d,J＝8.4Hz,1H),7.69-7.75(m,3H),7.53(d,J＝7.2Hz,1H),7.03-7.06(m,3H),6.72(d,J＝10.0Hz,1H),3.98(s,3H),3.92(s,3H).13C-NMR(100MHz,CDCl3)δ185.7,149.1,148.8,144.7,141.8,133.6,131.9,131.1,130.9,130.3,129.7,128.7,127.9,127.4,126.9,126.8,122.7,113.4,111.1,56.0(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1178.
6-(benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物6e):
Orange solid,mp 148-150℃.1H-NMR(400MHz,CDCl3)δ8.64(d,J＝7.2Hz,1H),8.30(d,J＝8.4Hz,1H),7.70-7.75(m,3H),7.49(d,J＝7.2Hz,1H),6.93-6.96(m,3H),6.73(d,J＝9.6Hz,1H),6.07(s,2H).13C-NMR(100MHz,CDCl3)δ185.7,147.8,147.7,144.4,141.8,133.5,133.1,131.0,130.8,130.3,129.7,128.7,127.9,127.5,127.0,126.9,123.9,110.6,108.4,101.4.HRMS(ESI)calcd.for[C20H12O3+Na]+323.0679,found323.0687.
6-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物6f):
Orange solid,mp 148-150℃.1H NMR(400MHz,CDCl3)δ8.62(d,J＝7.3Hz,1H),8.31(d,J＝8.3Hz,1H),7.78–7.67(m,3H),7.54(d,J＝7.3Hz,1H),6.71(d,J＝8.2Hz,1H),6.70(s,2H),3.95(s,3H),3.89(s,6H).13C NMR(101MHz,CDCl3)δ185.6,153.2(2C),144.8,141.7,138.1,134.9,133.5,130.9,130.8,130.3,129.7,128.8,127.8,127.3,127.0(2C),107.6(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1271.
6-(3-nitrophenyl)-1H-phenalen-1-one(化合物6g):
Orange solid,mp 148-150℃.1H-NMR(400MHz,CDCl3)δ8.64(d,J＝7.2Hz,1H),8.38(s,1H),8.36(d,J＝9.6Hz,1H),8.12(d,J＝8.0Hz,1H),7.73-7.87(m,5H),7.57(d,J＝7.2Hz,1H),6.76(d,J＝9.6Hz,1H).13C NMR(100MHz,CDCl3)δ185.4,148.4,141.6,141.5,141.0,136.1,132.3,130.7,130.5,130.2,129.8,129.5,129.4,128.1,127.9(2C),127.6,124.8,123.0.HRMS(ESI)calcd.for[C19H11NO3+Na]+324.0631,found 324.0637.
7-Phenyl-1H-phenalen-1-one(化合物7a):
Orange solid,mp 82-84℃.1H NMR(400MHz,CDCl3)δ8.67(dd,J＝7.6,1.0Hz,1H),8.08(d,J＝8.6Hz,1H),7.81–7.68(m,3H),7.60–7.46(m,6H),6.76(d,J＝9.7Hz,1H).13CNMR(100MHz,CDCl3)δ185.5,147.7,142.1,139.4,131.4,130.7,130.4,130.2(2C),130.1,129.0,128.7,128.4(2C),128.3,128.2,128.0,127.9,126.5.
7-(4-Methoxyphenyl)-1H-phenalen-1-one(化合物7b):
Orange solid,mp 183-185℃.1H NMR(400MHz,CDCl3)δ8.64(d,J＝7.6Hz,1H),8.11(d,J＝8.5Hz,1H),7.86–7.66(m,3H),7.52(dd,J＝8.4,7.2Hz,1H),7.43(d,J＝8.6Hz,2H),7.06(d,J＝8.6Hz,2H),6.74(d,J＝9.7Hz,1H),3.90(s,3H).13C NMR(100MHz,CDCl3)δ185.5,159.7,147.6,142.0,131.6,131.5(2C),131.4,130.8,130.5,130.1,129.0,128.3,128.2,128.0,127.9,126.4,114.0(2C),55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1061.
7-(2,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物7c):
Orange solid,mp 153-155℃.1H NMR(400MHz,CDCl3)δ8.66(d,J＝7.6Hz,1H),7.84(d,J＝8.5Hz,1H),7.78–7.66(m,3H),7.52–7.44(m,1H),7.19(d,J＝8.7Hz,1H),6.74(d,J＝9.7Hz,1H),6.65(d,J＝7.0Hz,1H),6.64(s,1H),3.91(s,3H),3.69(s,3H).13C NMR(100MHz,CDCl3)δ185.6,161.3,157.9,144.8,142.0,132.3,131.4,131.2,131.2,130.0,129.2,128.9,128.6,127.9,127.7,126.0,120.8,104.6,98.9,55.5(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1170.
7-(3,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物7d):
Orange solid,mp 189-191℃.1H NMR(400MHz,CDCl3)δ8.64(d,J＝7.6Hz,1H),8.13(d,J＝8.4Hz,1H),7.86–7.62(m,3H),7.53(dd,J＝8.5,7.1Hz,1H),7.13–6.91(m,3H),6.73(d,J＝9.7Hz,1H),3.97(s,3H),3.91(s,3H).13C NMR(100MHz,CDCl3)δ185.5,149.2,148.8,147.7,142.1,131.9,131.4,130.8,130.5,130.1,129.0,128.4,128.2,127.9(2C),126.4,122.9,113.4,111.1,56.08(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1175.
7-(Benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物7e):
Orange solid,mp 139-141℃.1H NMR(400MHz,CDCl3)δ8.65(d,J＝7.6Hz,1H),8.14(d,J＝8.6Hz,1H),7.84–7.74(m,2H),7.71(d,J＝7.6Hz,1H),7.55(dd,J＝8.4,7.2Hz,1H),6.98(d,J＝7.2Hz,1H),6.97(s,2H),6.76(d,J＝9.8Hz,1H),6.08(s,2H).13C NMR(100MHz,CDCl3)δ185.5,147.8(2C),147.4,142.1,133.1,131.4,130.6,130.5,130.1,129.0,128.5,128.3,128.0(2C),126.5,124.0,110.6,108.4,101.4.HRMS(ESI)calcd.for[C20H12O3+H]+301.0859,found301.0858.
7-(3,4,5-Trimethoxyphenyl)-1H-phenalen-1-one(化合物7f):
Orange solid,mp 184-186℃.1H NMR(400MHz,CDCl3)δ8.65(d,J＝7.6Hz,1H),8.16(d,J＝8.5Hz,1H),7.85–7.69(m,3H),7.61–7.52(m,1H),6.87–6.67(m,3H),3.97(s,3H),3.91(s,6H).13C NMR(100MHz,CDCl3)δ185.4,153.1(2C),147.7,142.1,138.0,134.9,131.5,130.6,130.5,129.9,129.0,128.6,128.1,128.0,127.9,126.6,107.5(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1270.
7-(3-nitrophenyl)-1H-phenalen-1-one(化合物7g):
Orange solid,mp 148-150℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.6Hz,1H),8.39(s,1H),8.37(d,J＝8.4Hz,1H),7.92(d,J＝8.6Hz,1H),7.85(d,J＝7.5Hz,1H),7.80(d,J＝8.7Hz,2H),7.74(t,J＝7.3Hz,2H),7.59(t,J＝7.8Hz,1H),6.77(d,J＝9.8Hz,1H).13C NMR(100MHz,CDCl3)δ185.3,148.3,144.4,142.2,141.0,136.1,131.6,130.2,129.9,129.6,129.4(2C),129.2,128.4,128.2,127.9,127.3,124.9,123.1.HRMS(ESI)calcd.for[C19H11NO3+H]+302.0812,found302.0816.
8-Phenyl-1H-phenalen-1-one(化合物8a):
Orange solid,mp:140–142℃.1H NMR(400MHz,CDCl3)δ8.89(d,J＝1.9Hz,1H),8.39(d,J＝1.8Hz,1H),8.07(d,J＝8.0Hz,1H),7.81–7.77(m,2H),7.75(s,1H),7.74(d,J＝6.1Hz,1H),7.61(dd,J＝8.2,7.1Hz,1H),7.55–7.50(m,2H),7.46–7.40(m,1H),6.75(d,J＝9.8Hz,1H).13C NMR(100MHz,CDCl3)δ185.7,141.8,140.1,139.6,132.7,132.4,132.1,131.2,129.9,129.7,129.3,129.1,128.2,127.8,127.5,127.0,126.7.HRMS(ESI)calcd.for[C19H12O+Na]+279.0780,found 279.0785.
8-(4-methoxyphenyl)-1H-phenalen-1-one(化合物8b):
Orange solid,mp:146-148℃.1H NMR(400MHz,CDCl3)δ8.84(d,J＝1.9Hz,1H),8.30(d,J＝1.8Hz,1H),8.02(d,J＝8.1Hz,1H),7.75–7.66(m,4H),7.57(dd,J＝8.2,7.1Hz,1H),7.07–7.01(m,2H),6.73(d,J＝9.7Hz,1H),3.88(s,3H).13C NMR(100MHz,CDCl3)δ185.7,159.9,141.7,139.7,132.8,132.0,131.9,131.6,130.9,129.8,129.3,129.3,128.6,127.7,126.9,126.3,114.6,55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1075.
8-(2,4-dimethoxyphenyl)-1H-phenalen-1-one(化合物8c):
Orange solid,mp:150-152℃.1H NMR(400MHz,CDCl3)δ8.81(d,J＝1.7Hz,1H),8.32(d,J＝1.7Hz,1H),8.04(d,J＝8.2Hz,1H),7.76(d,J＝9.8Hz,1H),7.73(d,J＝7.0Hz,1H),7.62–7.54(m,1H),7.39(d,J＝8.1Hz,1H),6.74(d,J＝9.7Hz,1H),6.64(d,J＝2.4Hz,1H),6.61(brs,1H),3.89(s,3H),3.84(s,3H).13C NMR(100MHz,CDCl3)δ185.9,161.0,157.6,141.7,137.7,134.9,132.5,132.4,132.1,131.6,130.9,129.3,129.1,127.7,126.6,126.3,122.0,104.9,99.0,55.7,55.5.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1180.
8-(3,4-dimethoxyphenyl)-1H-phenalen-1-one(化合物8d):
Orange solid,mp:147-149℃.1H NMR(400MHz,CDCl3)δ8.84(d,J＝1.9Hz,1H),8.32(d,J＝1.8Hz,1H),8.05(d,J＝8.2Hz,1H),7.75(d,J＝9.8Hz,1H),7.72(d,J＝7.0Hz,1H),7.60(dd,J＝8.1,7.2Hz,1H),7.33(dd,J＝8.3,2.1Hz,1H),7.30–7.25(m,1H),7.00(d,J＝8.3Hz,1H),6.75(d,J＝9.7Hz,1H),4.02(s,3H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ185.8,149.5,149.3,141.8,139.9,132.7,132.5,132.0,131.8,131.1,129.8,129.4,129.2,127.7,127.0,126.4,120.0,111.6,110.556.2,56.0.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1169.
8-(benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物8e):
Orange solid,mp:148-150℃.1H NMR(400MHz,CDCl3)δ8.78(d,J＝1.7Hz,1H),8.26(d,J＝1.7Hz,1H),8.02(d,J＝8.2Hz,1H),7.75–7.68(m,2H),7.61–7.54(m,1H),7.27–7.24(m,1H),7.23(s,1H),6.94(d,J＝8.5Hz,1H),6.73(d,J＝9.7Hz,1H),6.04(s,2H).13CNMR(100MHz,CDCl3)δ185.7,148.5,147.8,141.8,139.8,133.9,132.7,132.0,131.8,131.1,129.7,129.4,129.2,127.7,127.0,126.4,121.3,108.9,107.8,101.4.HRMS(ESI)calcd.for[C20H12O3+H]+301.0859,found 301.0859.
8-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物8f):
Orange solid,mp:146-148℃.1H NMR(400MHz,CDCl3)δ8.83(d,J＝1.6Hz,1H),8.33(d,J＝1.5Hz,1H),8.08(d,J＝8.2Hz,1H),7.75(t,J＝7.8Hz,2H),7.64–7.59(m,1H),6.95(s,2H),6.75(d,J＝9.8Hz,1H),3.99(s,6H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ185.7,153.8,141.8,140.2,138.3,135.6,132.7,132.3,132.1,131.3,129.8,129.5,129.3,127.8,127.1,126.6,104.8,61.0,56.4.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1276.
8-(3-nitrophenyl)-1H-phenalen-1-one(化合物8g):
Orange solid,mp:150-152℃.1H NMR(400MHz,CDCl3)δ8.89(d,J＝1.9Hz,1H),8.65(t,J＝1.9Hz,1H),8.46(d,J＝1.8Hz,1H),8.32–8.27(m,1H),8.16–8.10(m,2H),7.81(dd,J＝8.2,3.3Hz,2H),7.74–7.65(m,2H),6.78(d,J＝9.8Hz,1H).13C NMR(100MHz,CDCl3)δ185.5,148.9,141.9,141.4,137.5,133.4,132.8,132.7,132.2,131.9,130.2,130.1,129.3,128.9,127.9,127.6,127.2,122.9,122.3.HRMS(ESI)calcd.for[C19H11NO3+Na]+324.0631,found324.0630.
9-Phenyl-1H-phenalen-1-one(化合物9a):
Orange solid,mp 82-84℃.1H-NMR(400MHz,CDCl3)δ7.90(d,J＝8.4Hz,1H,Ar-H),7.76(d,J＝8.4Hz,1H,Ar-H),7.48(d,J＝6.8Hz,1H,Ar-H),7.30-7.42(m,7H,Ar-H；1H,-CH＝CH-),6.49(d,J＝10.0Hz,1H,-CH＝CH-).13C-NMR(100MHz,CDCl3)δ185.8,147.6,143.0,140.7,134.0,131.9,131.7,131.6(2C),130.3,128.4(3C),128.3(2C),128.1,127.3,126.5,125.9.HRMS(ESI)calcd.for[C19H12O+Na]+279.0780,found 279.0785.
9-(4-Methoxyphenyl)-1H-phenalen-1-one(化合物9b):
Orange solid,mp 183-185℃.1H-NMR(400MHz,CDCl3)δ8.15(d,J＝8.0Hz,1H,Ar-H),8.03(d,J＝8.4Hz,1H,Ar-H),7.77(d,J＝6.8Hz,1H,Ar-H),7.69(d,J＝9.6Hz,1H,-CH＝CH-),7.59-7.63(m,2H,Ar-H),7.37(d,J＝8.8Hz,2H,Ar-H),7.03(d,J＝8.8Hz,2H,Ar-H),6.63(d,J＝10.0Hz,1H,-CH＝CH-),3.90(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ185.9,159.0,147.5,140.3,134.9,133.7,131.9,131.7,131.6,131.4,130.6,129.4(2C),128.5,128.4,126.2,125.9,113.8(2C),55.3(2C).HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1075.
9-(2,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物9c):
Orange solid,mp 153-155℃.1H-NMR(400MHz,CDCl3)δ8.16(d,J＝8.0Hz,1H,Ar-H),8.01(d,J＝8.0Hz,1H,Ar-H),7.73(d,J＝7.2Hz,1H,Ar-H),7.67(d,J＝10.0Hz,1H,-CH＝CH-),7.56-7.62(m,2H,Ar-H),7.16(d,J＝8.0Hz,1H,Ar-H),6.60-6.66(m,2H,Ar-H；1H,-CH＝CH-),3.91(s,3H,-OCH3),3.73(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ185.7,160.5,157.6,143.5,140.1,133.7,132.1,131.7,131.6,131.0,130.2,129.3,128.4,128.2,127.0,126.1,124.9,104.6,98.8,55.6,55.4.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1180.
9-(3,4-Dimethoxyphenyl)-1H-phenalen-1-one(化合物9d):
Orange solid,mp 189-191℃.1H-NMR(400MHz,CDCl3)δ8.10(d,J＝8.0Hz,1H,Ar-H),7.98(d,J＝8.4Hz,1H,Ar-H),7.71(d,J＝6.8Hz,1H,Ar-H),7.63(d,J＝9.6Hz,1H,-CH＝CH-),7.54-7.59(m,2H,Ar-H),6.93-6.95(m,3H,Ar-H),6.58(d,J＝10.0Hz,1H,-CH＝CH-),3.93(s,3H,-OCH3),3.87(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ185.7,148.8,148.5,147.4,140.2,135.4,133.6,131.9,131.7,131.6,131.4,130.5,128.4,128.4,126.2,126.0,120.4,111.8,111.2,55.9(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1169.
9-(Benzo[d][1,3]dioxol-5-yl)-1H-phenalen-1-one(化合物9e):
Orange solid,mp 139-141℃.1H-NMR(400MHz,CDCl3)δ8.10(d,J＝8.0Hz,1H,Ar-H),7.98(d,J＝7.6Hz,1H,Ar-H),7.72(d,J＝6.4Hz,1H,Ar-H),7.64(d,J＝9.6Hz,1H,-CH＝CH-),7.54-7.58(m,2H,Ar-H),6.90(d,J＝7.2Hz,1H,Ar-H),6.82-6.85(m,2H,Ar-H),6.58(d,J＝9.2Hz,1H,-CH＝CH-),6.00(s,2H,-OCH2-).13C-NMR(100MHz,CDCl3)δ185.7,147.6,147.2,147.0,140.3,136.6,133.8,131.8(3C),131.7,131.5,130.5,128.4,126.4,126.2,121.3,109.0,108.5,101.1.HRMS(ESI)calcd.for[C20H12O3+H]+301.0859,found 301.0859.
9-(3,4,5-Trimethoxyphenyl)-1H-phenalen-1-one(化合物9f):
Orange solid,mp 184-186℃.1H-NMR(400MHz,CDCl3)δ8.17(d,J＝8.0Hz,1H,Ar-H),8.05(d,J＝8.0Hz,1H,Ar-H),7.80(d,J＝8.0Hz,1H,Ar-H),7.71(d,J＝8.0Hz,1H,-CH＝CH-),7.60-7.65(m,2H,Ar-H),6.62(d,J＝8.0Hz,1H,-CH＝CH-),6.58(s,2H,Ar-H),3.94(s,3H,-OCH3),3.89(s,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ185.6,153.2(2C),147.5,140.5,138.6,137.2,133.7,131.8(2C),131.6,131.5,130.5,128.5,128.4,126.5126.0,105.0(2C),61.0,56.1(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1278.
实施例2：目标化合物4h-n,5h-n,6h-n,7h-n,8h-n,9h-m的合成(以4h为例)
将化合物4a(50.0mg,0.2mmol)溶解在20.0mL的甲苯中，冷却到0摄氏度，然后加入氢氧化三甲基苄铵(0.03mL,40wt％in MeOH)和过氧叔丁醇(0.03mL,70wt％)，10分钟后，反应恢复至室温，搅拌45分钟后，第二批等量的氢氧化三甲基苄铵和过氧叔丁醇继续加入其中，4小时内检测反应彻底完成，然后用饱和硫代硫酸钠溶液淬灭反应，之后用20.0mL甲苯萃取，再用50.0mL水洗，将甲苯层用无水硫酸钠干燥，接着加入无水的对甲苯磺酸(60mg)，搅拌过夜，最后用100.0mL EtOAc/H2O(1:1)萃取，将有几层浓缩，过硅胶柱，分离纯化得到4h(41mg,77.0％)。参照该方法分别制备如下化合物，化合物理化数据如下：2-Hydroxy-4-phenyl-1H-phenalen-1-one(化合物4h):
Red solid,mp 175-177℃.1H-NMR(400MHz,CDCl3)δ8.68(d,J＝8.0Hz,1H,Ar-H),8.16(d,J＝8.0Hz,1H,Ar-H),7.85(d,J＝8.0Hz,1H,Ar-H),7.70(t,J＝8.0Hz,1H,Ar-H),7.48(d,J＝8.0Hz,1H,Ar-H),7.36-7.43(m,5H,Phenly-H),7.18(s,1H,-CH＝COH-),6.91(s,1H,OH).13C-NMR(100MHz,CDCl3)δ179.9,149.4,143.9,139.6,136.5,131.5,131.4,130.3(2C),129.8,129.6,128.5(2C),128.0,127.7,126.6,125.1,124.8,112.5.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found 273.0903.
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one(化合物4i):
Red solid,mp 221-223℃.1H-NMR(400MHz,CDCl3)δ8.80(d,J＝7.2Hz,1H,Ar-H),8.28(d,J＝7.6Hz,1H,Ar-H),7.96(d,J＝8.4Hz,1H,Ar-H),7.82(t,J＝7.6Hz,1H,Ar-H),7.60(d,J＝8.4Hz,1H,Ar-H),7.43(d,J＝8.4Hz,2H,Ar-H),7.36(s,1H,-CH＝COH-),7.08(d,J＝8.4Hz,2H,Ar-H),6.99(s,1H,-OH),3.93(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.8,159.6,149.3,143.8,136.4,131.8,131.6(2C),131.5,131.2,129.9,129.6,127.6,126.4,124.9,114.0(2C),113.9,112.6,55.4.HRMS(ESI)calcd.for[C20H14O3+H]+303.1016,found 303.1015.
4-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物4j):
Red solid,mp 217-219℃.1H-NMR(400MHz,CDCl3)δ8.74(d,J＝8.0Hz,1H,Ar-H),8.23(d,J＝8.0Hz,1H,Ar-H),7.89(d,J＝8.0Hz,1H,Ar-H),7.76(t,J＝8.0Hz,1H,Ar-H),7.52(d,J＝8.0Hz,1H,Ar-H),7.15(d,J＝8.0Hz,1H,Ar-H),7.09(s,1H,Ar-H),6.94(s,1H,-OH),6.63(d,J＝8.0Hz,1H,Ar-H),6.62(s,1H,-CH＝COH-),3.89(s,3H,-OCH3),3.74(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ180.1,161.3,157.8,149.1,140.9,136.4,132.7,131.4,131.1,130.9,129.1,127.6,126.4,126.2,124.9,120.8,113.1,104.7,99.0,55.6,55.5.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1120.
4-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物4k):
Red solid,mp 178-180℃.1H-NMR(400MHz,CDCl3)δ8.79(d,J＝8.0Hz,1H,Ar-H),8.27(d,J＝8.0Hz,1H,Ar-H),7.94(d,J＝8.0Hz,1H,Ar-H),7.81(t,J＝8.0Hz,1H,Ar-H),7.59(d,J＝8.0Hz,1H,Ar-H),7.34(s,1H,Ar-H),6.96-7.02(m,4H,Ar-H),3.98(s,3H,-OCH3),3.94(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,149.4,149.2,148.9,143.9,136.5,132.2,131.5,131.3,129.9,129.6,127.7,126.5,125.0,124.9,123.1,113.5,112.6,111.2,56.1,56.0.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1117.
4-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物4l):
Red solid,mp 174-176℃.1H-NMR(400MHz,CDCl3)δ8.78(d,J＝8.0Hz,1H,Ar-H),8.27(d,J＝8.0Hz,1H,Ar-H),7.93(d,J＝8.0Hz,1H,Ar-H),7.80(t,J＝8.0Hz,1H,Ar-H),7.54(d,J＝8.0Hz,1H,Ar-H),7.33(s,1H,Ar-H),6.91-6.97(m,4H,Ar-H),6.07(s,2H,-OCH2-).13C-NMR(100MHz,CDCl3)δ179.9,149.4,147.8,143.6,136.5,133.4,131.6,131.3,129.9,129.7,127.7,126.6,125.1,124.9,124.3,123.2,112.5,110.7,108.4,101.4.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found 317.0810.
2-Hydroxy-4-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物4m):
Red solid,mp 203-205℃.1H-NMR(400MHz,CDCl3)δ8.78(d,J＝8.0Hz,1H,Ar-H),8.27(d,J＝8.0Hz,1H,Ar-H),7.94(d,J＝8.0Hz,1H,Ar-H),7.80(t,J＝8.0Hz,1H,Ar-H),7.59(d,J＝8.0Hz,1H,Ar-H),7.32(s,1H,-CH＝COH-),7.02(s,1H,-OH),6.66(s,2H,Ar-H),3.96(s,3H,-OCH3),3.91(s,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,153.1(2C),149.4,143.9,138.0,136.5,135.2,131.6,131.4,129.6,129.5,127.7,126.7,125.2,124.8,112.4,107.7(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found 363.1226.
2-Hydroxy-4-(3-nitrophenyl)-1H-phenalen-1-one(化合物4n):
Red solid,mp 218-220℃.1H-NMR(400MHz,CDCl3)δ8.81(d,J＝8.0Hz,1H,Ar-H),8.31-8.36(m,3H,Ar-H),8.02(d,J＝8.0Hz,1H,Ar-H),7.86(t,J＝8.0Hz,1H,Ar-H),7.80(d,J＝8.0Hz,1H,Ar-H),7.72(t,J＝8.0Hz,1H,Ar-H),7.58(d,J＝8.0Hz,1H,Ar-H),7.09(s,1H,-CH＝COH-).13C-NMR(100MHz,CDCl3)δ178.8,148.8,147.3,140.3,139.6,135.8,135.3,131.1,130.7,128.9,128.5,128.1,126.7,126.2,124.6,123.8,123.7,121.9,110.1.HRMS(ESI)calcd.for[C19H11NO4+H]+318.0761,found 318.0761.
2-Hydroxy-5-phenyl-1H-phenalen-1-one(化合物5h):
Red solid,mp:176-178℃.1H NMR(400MHz,CDCl3)δ8.70(dd,J＝7.4,0.9Hz,1H),8.31(d,J＝8.0Hz,1H),8.09(d,J＝1.3Hz,1H),7.95(d,J＝1.2Hz,1H),7.82(t,J＝7.7Hz,1H),7.76–7.71(m,2H),7.53(t,J＝7.5Hz,2H),7.44(t,J＝7.4Hz,1H),7.21(s,1H),7.06(s,1H).13C NMR(100MHz,CDCl3)δ180.5,149.8,140.3,139.9,136.7,132.4,130.9,130.1,129.1,128.9,128.1,127.3,127.3,127.2,123.6,113.8.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found273.0902.
2-Hydroxy-5-(4-methoxyphenyl)-1H-phenalen-1-one(化合物5i):
Red solid,mp:181–183℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.3Hz,1H),8.28(d,J＝8.0Hz,1H),8.03(d,J＝1.4Hz,1H),7.91(d,J＝1.2Hz,1H),7.80(t,J＝7.7Hz,1H),7.70–7.65(m,2H),7.19(s,1H),7.04(dd,J＝8.0,7.2Hz,2H),7.02(s,1H),3.89(s,3H).13CNMR(100MHz,CDCl3)δ180.5,159.8,149.8,139.8,136.5,132.6,132.3,130.5,129.9,128.8,128.4,127.3,127.1,126.5,123.4,114.6,113.7,55.4.HRMS(ESI)calcd.for[C20H14O3+H]+303.1016,found303.1015.
5-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物5j):
Red solid,mp:218-220℃.1H NMR(400MHz,CDCl3)δ8.71(dd,J＝7.4,1.0Hz,1H),8.27(d,J＝7.4Hz,1H),8.00(d,J＝1.3Hz,1H),7.91(d,J＝1.2Hz,1H),7.79(t,J＝7.7Hz,1H),7.37(d,J＝8.5Hz,1H),7.19(s,1H),6.99(s,1H),6.65(d,J＝2.4Hz,1H),6.63(s,1H),3.89(s,3H),3.84(s,3H).13C NMR(100MHz,CDCl3)δ180.6,161.0,157.7,149.6,137.7,136.5,133.1,132.3,131.3,130.5,129.5,127.7,127.3,126.8,123.3,122.2,114.1,105.0,99.2,55.7,55.5.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1116.
5-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物5k):
Red solid,mp:177-179℃.1H NMR(400MHz,CDCl3)δ8.73–8.68(m,1H),8.31(d,J＝8.0Hz,1H),8.05(d,J＝1.2Hz,1H),7.92(d,J＝1.1Hz,1H),7.82(t,J＝7.7Hz,1H),7.34–7.28(m,1H),7.26(d,J＝2.0Hz,1H),7.21(s,1H),7.07–7.01(m,2H),4.04(s,3H),3.99(s,3H).13C NMR(100MHz,CDCl3)δ180.5,149.8,149.5,149.4,140.0,136.5,132.8,132.5,130.6,129.9,128.8,127.3,127.2,126.6,123.4,119.8,113.7,111.8,110.6,56.2,56.1.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1118.
5-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物5l):
Red solid,mp:176-178℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.3Hz,1H),8.27(d,J＝8.0Hz,1H),7.99(s,1H),7.87(s,1H),7.80(t,J＝7.7Hz,1H),7.22–7.15(m,3H),7.01(s,1H),6.95(d,J＝8.5Hz,1H),6.05(s,2H).13C NMR(100MHz,CDCl3)δ180.5,149.8,148.5,147.8,139.9,136.6,134.2,132.5,130.7,130.0,128.9,127.3,127.2,126.8,123.5,121.0,113.7,108.9,107.7,101.4.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found 317.0813.
2-Hydroxy-5-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物5m):
Red solid,mp:206-208℃.1H NMR(400MHz,CDCl3)δ8.72(d,J＝7.4Hz,1H),8.33(d,J＝8.0Hz,1H),8.05(s,1H),7.91(s,1H),7.84(t,J＝7.7Hz,1H),7.23(s,1H),7.03(s,1H),6.92(s,2H),3.99(s,6H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ180.5,153.8,149.8,140.4,138.3,136.6,135.9,132.4,130.9,130.0,128.9,127.4,127.3,127.1,123.7,113.6,104.7,61.1,56.4.HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found 363.1220.
2-Hydroxy-5-(3-nitrophenyl)-1H-phenalen-1-one(化合物5n):
Red solid,mp:221-223℃.1H NMR(400MHz,DMSO-d6)δ9.80(s,1H),8.68(s,1H),8.58-8.52(m,3H),8.37(d,J＝7.6Hz,1H),8.30(d,J＝5.0Hz,2H),7.94(t,J＝7.7Hz,1H),7.86(t,J＝7.9Hz,1H),7.29(s,1H).13C NMR(100MHz,DMSO-d6)δ180.4,151.5,149.0,141.2,137.0,136.9,133.9,132.4,131.1,130.9,130.1,128.6,128.5,128.1,127.3,123.8,123.2,121.9,115.1.HRMS(ESI)calcd.for[C19H11NO4+H]+318.0761,found318.0759.
2-Hydroxy-6-phenyl-1H-phenalen-1-one(化合物6h):
Red solid,mp 175-177℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.3Hz,1H),8.35(d,J＝8.3Hz,1H),7.75(t,J＝7.7Hz,2H),7.58–7.47(m,6H),7.18(s,1H),7.01(s,1H).13CNMR(100MHz,CDCl3)δ180.4,149.3,142.7,139.4,135.3,131.1,130.6,130.3(2C),130.2,128.4(2C),128.1,127.9,127.7,127.6,126.7,124.6,113.9.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found 273.0902.
2-Hydroxy-6-(4-methoxyphenyl)-1H-phenalen-1-one(化合物6i):
Red solid,mp 180–182℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.3Hz,1H),8.37(d,J＝8.3Hz,1H),7.77-7.71(m,2H),7.51(d,J＝7.3Hz,1H),7.43(d,J＝8.4Hz,2H),7.18(s,1H),7.07(d,J＝8.4Hz,2H),7.00(s,1H),3.91(s,3H).13C NMR(100MHz,CDCl3)δ180.4,159.5,149.2,142.6,135.4,131.7,131.5(2C),131.0,130.8,130.3,128.0,127.7,127.2,126.6,124.7,114.0,113.9(2C),55.4.HRMS(ESI)calcd.for[C20H14O3+Na]+325.0835,found325.0834.
6-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物6j):
Red solid,mp 217-219℃.1H NMR(400MHz,CDCl3)δ8.81–8.70(m,1H),8.09(d,J＝8.3Hz,1H),7.71(dd,J＝8.0,7.8Hz,2H),7.48(d,J＝7.3Hz,1H),7.20(d,J＝8.8Hz,1H),7.18(s,1H),6.97(s,1H),6.68–6.60(m,2H),3.91(s,3H),3.69(s,3H).13C NMR(100MHz,CDCl3)δ180.4,161.1,158.0,149.2,139.6,135.8,132.5,131.4,130.9,130.3,128.9,127.6,127.4,126.3,124.5,120.8,114.0,104.6,98.9,55.5(2C).HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found333.1126.
6-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物6k):
Red solid,mp 178-180℃.1H NMR(400MHz,CDCl3)δ8.76(dd,J＝7.3,0.9Hz,1H),8.40(dd,J＝8.3,1.0Hz,1H),7.75(dd,J＝13.0,5.0Hz,1H),7.72(d,J＝7.4Hz,1H),7.54(d,J＝7.3Hz,1H),7.18(s,1H),7.06–6.99(m,4H),3.99(s,3H),3.93(s,3H).13C NMR(101MHz,CDCl3)δ180.4,149.2,149.0,148.8,142.6,135.3,132.0,131.1,130.8,130.2,128.0,127.7,127.3,126.7,124.6,122.9,114.0,113.6,111.1,56.0(2C).HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1116.
6-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物6l):
Red solid,mp 174-176℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.2Hz,1H),8.39(d,J＝8.2Hz,1H),7.76(t,J＝7.8Hz,1H),7.71(d,J＝7.4Hz,1H),7.50(d,J＝7.3Hz,1H),7.17(s,1H),7.00–6.92(m,4H),6.08(s,2H).13C NMR(100MHz,CDCl3)δ180.3,149.3,147.7,142.3,135.2,133.2,133.1,131.1,130.7,130.2,128.0,127.6,127.5,126.7,124.7,124.1,113.9,110.8,108.3,101.3.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found317.0814.
2-Hydroxy-6-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物6m):
Red solid,mp 203-205℃.1H NMR(400MHz,CDCl3)δ8.77(dd,J＝7.3,1.0Hz,1H),8.41(dd,J＝8.3,1.0Hz,1H),7.81–7.75(m,1H),7.74(d,J＝7.4Hz,1H),7.55(d,J＝7.3Hz,1H),7.19(s,1H),6.99(s,1H),6.70(s,2H),3.96(s,3H),3.90(s,6H).13C NMR(100MHz,CDCl3)δ180.4,153.1(2C),149.3,142.7,138.0,135.2,134.9,131.1,130.7,130.0(2C),127.8,127.7,126.8,124.6,113.9,107.8(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found363.1223.
2-Hydroxy-6-(3-nitrophenyl)-1H-phenalen-1-one(化合物6n):
Red solid,mp 218-220℃.1H NMR(400MHz,CDCl3)δ8.79(d,J＝7.3Hz,1H),8.41–8.33(m,2H),8.21(d,J＝8.3Hz,1H),7.84(d,J＝7.7Hz,1H),7.81–7.76(m,2H),7.73(t,J＝7.9Hz,1H),7.57(d,J＝7.3Hz,1H),7.20(s,1H),7.02(s,1H).13C NMR(100MHz,CDCl3)δ179.4,148.6,140.0,138.4,135.2,133.1,130.3,129.1,128.8(2C),128.5,127.8,127.4,126.8,126.4,124.0,123.7,121.8,112.6.HRMS(ESI)calcd.for[C19H11NO4+H]+318.0761,found 318.0755.
2-Hydroxy-7-phenyl-1H-phenalen-1-one(化合物7h):
Red solid,mp 128-130℃.1H NMR(400MHz,CDCl3)δ8.77(d,J＝7.6Hz,1H),7.97(dd,J＝8.6,0.8Hz,1H),7.76(d,J＝7.6Hz,1H),7.72(d,J＝6.9Hz,1H),7.59–7.46(m,6H),7.19(s,1H),7.02(s,1H).13C NMR(100MHz,CDCl3)δ180.2,149.5,149.4(2C),139.3,130.8,130.5,130.3(2C),128.6,128.5,128.4(2C),128.3,128.1,127.1,126.6,124.8,114.1.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found 273.0906.
2-Hydroxy-7-(4-methoxyphenyl)-1H-phenalen-1-one(化合物7i):
Red solid,mp 186-188℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.6Hz,1H),8.02(d,J＝8.6Hz,1H),7.73(dd,J＝10.0,7.5Hz,2H),7.53(t,J＝7.8Hz,1H),7.46(d,J＝7.9Hz,2H),7.18(s,1H),7.08(d,J＝8.0Hz,2H),7.03(s,1H),3.92(s,3H).13C NMR(100MHz,CDCl3)δ180.1,159.9,149.4(2C),131.7,131.6(2C),130.8,130.5,130.4,128.7,128.5,128.1,126.9,126.3,124.9,113.9(3C),55.4.HRMS(ESI)calcd.for[C20H14O3+H]+303.1016,found 303.1015.
7-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物7j):
Red solid,mp 158-160℃.1H NMR(400MHz,CDCl3)δ8.75(d,J＝7.6Hz,1H),7.75(d,J＝8.5Hz,1H),7.72(d,J＝7.6Hz,1H),7.67(d,J＝7.0Hz,1H),7.46(dd,J＝8.4,7.2Hz,1H),7.19(d,J＝8.7Hz,1H),7.16(s,1H),7.02(s,1H),6.66(d,J＝2.3Hz,1H),6.64(s,1H),3.91(s,3H),3.70(s,3H).13C NMR(100MHz,CDCl3)δ180.3,161.3,157.9,149.3,146.6,132.5,131.2,130.7,130.4,129.1,129.0,128.4,126.6,126.5,124.6,120.7,114.0,104.5,98.8,55.5(2C).HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1116.
7-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物7k):
Red solid,mp 173-175℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.6Hz,1H),8.03(d,J＝8.5Hz,1H),7.75(d,J＝7.6Hz,1H),7.70(d,J＝7.0Hz,1H),7.56–7.48(m,1H),7.16(s,1H),7.08-7.03(m,4H),3.99(s,3H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ180.1,149.4(3C),148.9,132.0,130.7,130.4(2C),128.6,128.5,128.0,126.9,126.4,124.8,123.1,114.0,113.6,111.1,56.1,56.0.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found333.1118.
7-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物7l):
Red solid,mp 180-182℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.6Hz,1H),8.03(dd,J＝8.6,0.8Hz,1H),7.73(d,J＝6.2Hz,1H),7.71(d,J＝5.2Hz,1H),7.54(dd,J＝8.5,7.1Hz,1H),7.18(s,1H),7.01-7.00(m,2H),6.97(s,2H),6.09(s,2H).13C NMR(100MHz,CDCl3)δ180.1,149.4,149.1,147.9,147.8,133.1,130.8,130.5,130.4,128.5,128.5,128.1,127.0,126.4,124.8,124.3,114.0,110.8,108.4,101.4.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found317.0813.
2-Hydroxy-7-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物7m):
Red solid,mp 176-178℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.6Hz,1H),8.07–8.00(m,1H),7.77(d,J＝7.6Hz,1H),7.72(d,J＝6.9Hz,1H),7.56(dd,J＝8.5,7.1Hz,1H),7.19(s,1H),7.03(s,1H),6.72(s,2H),3.97(s,3H),3.91(s,6H).13C NMR(100MHz,CDCl3)δ180.2,153.1(2C),149.5,149.4,138.2,134.9,130.7,130.5,130.4,128.5,127.9,127.1,126.6,124.8,114.1,107.7,104.6(2C),61.0,56.3(2C).HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found363.1220.
2-Hydroxy-7-(3-nitrophenyl)-1H-phenalen-1-one(化合物7n):
Red solid,mp 218-220℃.1H NMR(400MHz,CDCl3)δ8.80(d,J＝7.6Hz,1H),8.40(s,1H),8.39(d,J＝8.4Hz,1H),7.86(d,J＝7.6Hz,1H),7.83–7.74(m,4H),7.61–7.54(m,1H),7.20(s,1H),6.98(s,1H).13C NMR(100MHz,CDCl3)δ180.1,149.5,148.3,146.0,141.0,136.1,130.7,130.6,130.0,129.5,128.9,128.2,127.8,127.5,127.3,125.0,124.8,123.2,114.2.HRMS(ESI)calcd.for[C19H11NO4+H]+318.0761,found 318.0759.
2-Hydroxy-8-phenyl-1H-phenalen-1-one(化合物8h):
Red solid,mp:135-137℃.1H NMR(400MHz,CDCl3)δ8.99(d,J＝1.7Hz,1H),8.46(d,J＝1.6Hz,1H),7.98(d,J＝8.2Hz,1H),7.80(d,J＝7.6Hz,2H),7.70(d,J＝7.0Hz,1H),7.63–7.57(m,1H),7.54(t,J＝7.6Hz,2H),7.45(t,J＝7.3Hz,1H),7.17(s,1H),7.00(s,1H).13C NMR(100MHz,CDCl3)δ180.6,149.6,139.9,139.4,134.1,132.5,130.4,130.3,130.0,129.2,128.3,128.2,127.8,127.6,127.5,123.5,113.8.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found273.0902.
2-Hydroxy-8-(4-methoxyphenyl)-1H-phenalen-1-one(化合物8i):
Red solid,mp:190-192℃.1H NMR(400MHz,CDCl3)δ8.95(s,1H),8.40(s,1H),7.95(d,J＝8.0Hz,1H),7.74(d,J＝8.3Hz,2H),7.68(d,J＝6.9Hz,1H),7.59(t,J＝7.6Hz,1H),7.16(s,1H),7.06(d,J＝8.4Hz,2H),7.00(s,1H),3.90(s,3H).13C NMR(100MHz,CDCl3)δ180.6,159.9,149.6,139.6,133.4,132.6,131.8,130.2,130.0,129.9,128.6,128.2,127.8,127.5,114.6,113.8,55.5.HRMS(ESI)calcd.for[C20H14O3+H]+303.1016,found303.1015.
8-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物8j):
Red solid,mp:157-159℃.1H NMR(400MHz,CDCl3)δ8.90(d,J＝1.7Hz,1H),8.36(d,J＝1.6Hz,1H),7.92(d,J＝8.1Hz,1H),7.66(d,J＝7.0Hz,1H),7.59–7.52(m,1H),7.39(d,J＝8.1Hz,1H),7.15(s,1H),7.03(s,1H),6.64(d,J＝2.3Hz,1H),6.62(brs,1H),3.88(s,3H),3.84(s,3H).13C NMR(100MHz,CDCl3)δ180.6,161.1,157.7,149.6,137.4,136.6,133.2,132.2,131.6,130.0,129.9,128.2,127.1,127.0,123.1,121.8,113.7,105.1,99.1,55.7,55.5.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1116.
8-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物8k):
Red solid,mp:176-178℃.1H NMR(400MHz,CDCl3)δ8.93(d,J＝1.8Hz,1H),8.38(d,J＝1.8Hz,1H),7.95(d,J＝8.1Hz,1H),7.67(d,J＝6.9Hz,1H),7.61–7.55(m,1H),7.34(dd,J＝8.3,2.1Hz,1H),7.29–7.24(m,1H),7.15(s,1H),7.05–6.99(m,2H),4.02(s,3H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ180.6,149.6,149.5,149.4,139.7,133.6,132.5,132.3,130.3,130.0,129.9,128.2,127.7,127.6,123.2,120.0,113.9,111.7,110.5,56.2,56.0.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1118.
8-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物8l):
Red solid,mp:183-185℃.1H NMR(400MHz,CDCl3)δ8.87(s,1H),8.33(s,1H),7.92(d,J＝8.0Hz,1H),7.66(d,J＝6.7Hz,1H),7.57(t,J＝7.5Hz,1H),7.25(d,J＝6.6Hz,2H),7.13(s,1H),7.01(s,1H),6.95(d,J＝8.3Hz,1H),6.05(s,2H).13C NMR(100MHz,CDCl3)δ180.5,149.6,148.6,147.9,139.5,133.7,133.6,132.5,130.2,130.0,129.9,128.2,127.8,127.6,123.3,121.3,113.8,108.9,107.8,101.5.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found317.0813.
2-Hydroxy-8-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物8m):
Red solid,mp:175-177℃.1H NMR(400MHz,CDCl3)δ8.91(d,J＝1.7Hz,1H),8.38(d,J＝1.7Hz,1H),7.97(d,J＝8.1Hz,1H),7.68(d,J＝6.9Hz,1H),7.63–7.56(m,1H),7.15(s,1H),7.04(s,1H),6.95(s,2H),3.99(s,6H),3.94(s,3H).13C NMR(100MHz,CDCl3)δ180.6,153.8,149.6,140.0,138.4,135.3,133.9,132.4,130.5,130.1,129.9,128.2,127.7,127.7,123.4,113.9,104.8,61.1,56.4.HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found 363.1220.
2-Hydroxy-8-(3-nitrophenyl)-1H-phenalen-1-one(化合物8n):
Red solid,mp:225-227℃.1H NMR(400MHz,DMSO-d6)δ9.78(s,1H),8.91(d,J＝1.7Hz,1H),8.83(d,J＝1.8Hz,1H),8.69(t,J＝1.8Hz,1H),8.40(d,J＝7.8Hz,1H),8.32(dd,J＝8.1,1.7Hz,1H),8.16(d,J＝8.2Hz,1H),7.90–7.82(m,2H),7.74–7.67(m,1H),7.21(s,1H).13C NMR(100MHz,DMSO-d6)δ180.2,151.2,149.0,140.9,136.7,134.4,134.3,132.7,131.3,130.5,129.9,129.4,129.0,128.6,123.6,123.4,122.2,115.4.HRMS(ESI)calcd.for[C19H11NO4+H]+318.0761,found 318.0759.
2-Hydroxy-9-phenyl-1H-phenalen-1-one(化合物9h):
Red solid,mp 128-130℃.1H-NMR(400MHz,CDCl3)δ8.21(d,J＝8.0Hz,1H,Ar-H),7.92(d,J＝8.0Hz,1H,Ar-H),7.71(d,J＝8.0Hz,1H,Ar-H),7.51-7.61(m,2H,Ar-H),7.45-7.48(m,3H,Ar-H),7.37(d,J＝8.0Hz,2H,Ar-H),7.11(s,1H,-CH＝COH-),7.02(s,1H,-OH).13C-NMR(100MHz,CDCl3)δ180.3,149.8,149.0,142.3,135.6,131.5,131.1,130.7,129.7,128.8,128.3(2C),127.8(2C),127.6,127.0,125.0,123.6,112.7.HRMS(ESI)calcd.for[C19H12O2+H]+273.0910,found 273.0907.
2-Hydroxy-9-(4-methoxyphenyl)-1H-phenalen-1-one(化合物9i):
Red solid,mp 186-188℃.1H-NMR(400MHz,CDCl3)δ8.20(d,J＝8.4Hz,1H,Ar-H),7.92(d,J＝8.4Hz,1H,Ar-H),7.72(d,J＝7.2Hz,1H,Ar-H),7.57-7.61(m,2H,Ar-H),7.34(d,J＝8.4Hz,2H,Ar-H),7.12(s,1H,-CH＝COH-),7.08(s,1H,-OH),7.03(d,J＝8.4Hz,2H,Ar-H),3.89(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ180.3,159.3,149.9,149.0,135.5,134.3,131.5,131.3,130.6,129.7,129.4(2C),128.7,126.8,125.1,123.5,113.7(2C),112.6,55.3.HRMS(ESI)calcd.for[C20H14O3+H]+303.1016,found 303.1015.
9-(2,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物9j):
Red solid,mp 158-160℃.1H-NMR(400MHz,CDCl3)δ8.22(d,J＝8.0Hz,1H,Ar-H),7.92(d,J＝8.0Hz,1H,Ar-H),7.70(d,J＝8.0Hz,1H,Ar-H),7.57-7.60(m,2H,Ar-H),7.11-7.13(m,1H,Ar-H,1H,-CH＝COH-,1H,-OH),6.61-6.65(m,2H,Ar-H),3.89(s,3H,-OCH3),3.68(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ180.1,160.9,157.8,149.7,145.2,135.6,131.7,131.5,130.3,129.6,129.4,128.8,126.7,125.0,124.7,124.2,112.4,104.6,98.8,55.6,55.4.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1116.
9-(3,4-Dimethoxyphenyl)-2-hydroxy-1H-phenalen-1-one(化合物9k):
Red solid,mp 173-175℃.1H-NMR(400MHz,CDCl3)δ8.20(d,J＝8.0Hz,1H,Ar-H),7.92(d,J＝8.0Hz,1H,Ar-H),7.70(d,J＝8.0Hz,1H,Ar-H),7.58-7.62(m,2H,Ar-H),7.11(s,1H,Ar-H),7.09(s,1H,-CH＝COH-),6.95-7.01(m,2H,Ar-H),6.93(s,1H,-OH),3.96(s,3H,-OCH3),3.88(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ180.2,149.9,148.9,148.9,148.8,135.5,134.8,131.5,131.4,130.7,129.7,128.8,126.9,125.1,123.6,120.4,112.6,111.8,111.0,56.0,55.9.HRMS(ESI)calcd.for[C21H16O4+H]+333.1121,found 333.1115.
9-(Benzo[d][1,3]dioxol-5-yl)-2-hydroxy-1H-phenalen-1-one(化合物9l):
Red solid,mp 180-182℃.1H-NMR(400MHz,CDCl3)δ8.19(d,J＝8.0Hz,1H,Ar-H),7.92(d,J＝8.0Hz,1H,Ar-H),7.72(d,J＝8.0Hz,1H,Ar-H),7.57-7.59(m,2H,Ar-H),7.12(s,1H,Ar-H),7.07(s,1H,Ar-H),6.94(d,J＝8.0Hz,1H,Ar-H),6.83-6.86(m,1H,Ar-H,1H,-OH),6.05(s,2H,-OCH2-).13C-NMR(100MHz,CDCl3)δ180.2,149.9,148.7,147.6,147.3,135.9,135.6,131.5,131.4,130.7,129.7,128.8,126.9,125.0,123.7,121.4,112.7,109.0,108.4,101.2.HRMS(ESI)calcd.for[C20H12O4+H]+317.0808,found 317.0808.
2-Hydroxy-9-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物9m):
Red solid,mp 176-178℃.1H-NMR(400MHz,CDCl3)δ8.21(d,J＝8.0Hz,1H,Ar-H),7.93(d,J＝8.0Hz,1H,Ar-H),7.71(d,J＝8.0Hz,1H,Ar-H),7.60-7.63(m,2H,Ar-H),7.12(s,1H,Ar-H),7.09(s,1H,-OH),6.60(s,2H,Ar-H),3.97(s,3H,-OCH3),3.86(s,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ180.1,153.3(2C),149.8,148.8,137.9,137.7,135.5,131.6,131.2,130.8,129.7,128.8,127.0,125.0,123.6,112.7,105.3(2C),61.0,56.2(2C).HRMS(ESI)calcd.for[C22H18O5+H]+363.1227,found 363.1221.
实施例3目标化合物4o-u,5o-u,6o-u,7o-u,8o-u,9o-t的合成(以4o为例)
将化合物4h(54.0mg,0.2mmol)溶解在DMF(8.0mL)中，然后加入K2CO3(0.2g,1.4mmol)，搅拌10分钟后，加入CH3I(0.3mL)，整个反应液继续搅拌5个小时，将反应液用100.0mL CH2Cl2/H2O(1:1)萃取，分离有机层，浓缩，浸膏用硅胶柱分离纯化得到4o(49mg,76.0％)，洗脱剂为石油醚/乙酸乙酯(v/v＝1:7)。化合物理化数据如下：2-Methoxy-4-phenyl-1H-phenalen-1-one(化合物4o):
Orange solid,mp 107-109℃.1H-NMR(400MHz,CDCl3)δ8.74(dd,J＝8.0,4.0Hz,1H,Ar-H),8.18(dd,J＝8.0,4.0Hz,1H,Ar-H),7.89(d,J＝8.0Hz,1H,Ar-H),7.74(t,J＝8.0Hz,1H,Ar-H),7.46-7.55(m,6H,Phenly-H),7.02(s,1H,-CH＝COCH3-),3.76(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,153.2,142.6,139.8,135.4,131.3,131.2,130.2(2C),129.6(2C),129.1,128.5(2C),128.0,126.7,125.0,124.8,111.0,55.4.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1064.
2-Methoxy-4-(4-methoxyphenyl)-1H-phenalen-1-one(化合物4p):
Orange solid,mp 139-141℃.1H-NMR(400MHz,CDCl3)δ8.74(d,J＝6.8Hz,1H,Ar-H),8.18(d,J＝7.6Hz,1H,Ar-H),7.89(d,J＝8.4Hz,1H,Ar-H),7.74(t,J＝7.6Hz,1H,Ar-H),7.53(d,J＝8.4Hz,1H,Ar-H),7.43(d,J＝8.4Hz,2H,Ar-H),7.07(brs,2H,Ar-H；1H,-CH＝COCH3-),3.91(s,3H,-OCH3),3.78(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.6,159.5,153.1,142.3,135.2,132.1,131.4(2C),131.2,131.1,129.7,129.6,129.0,126.5,125.1,124.7,114.0(2C),111.2,55.4(2C).HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found317.1174.
4-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物4q):
Orange solid,mp 168-170℃.1H-NMR(400MHz,CDCl3)δ8.72(d,J＝8.0Hz,1H,Ar-H),8.17(d,J＝8.0Hz,1H,Ar-H),7.88(d,J＝8.0Hz,1H,Ar-H),7.74(t,J＝8.0Hz,1H,Ar-H),7.50(d,J＝8.0Hz,1H,Ar-H),7.20(d,J＝8.0Hz,1H,Ar-H),6.83(s,1H,-CH＝COCH3-),6.66(d,J＝8.0Hz,1H,Ar-H),6.64(s,1H,Ar-H),3.91(s,3H,-OCH3),3.76(s,3H,-OCH3),3.75(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,161.3,157.8,152.9,139.4,135.3,132.6,131.4,130.9,130.6,129.6,128.6,126.4,125.9,125.1,120.9,111.8,104.8,98.9,55.6,55.5,55.4.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1275.
4-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物4r):
Orange solid,mp 150-152℃.1H-NMR(400MHz,CDCl3)δ8.76(d,J＝8.0Hz,1H,Ar-H),8.20(d,J＝8.0Hz,1H,Ar-H),7.92(d,J＝8.0Hz,1H,Ar-H),7.78(t,J＝8.0Hz,1H,Ar-H),7.57(d,J＝8.0Hz,1H,Ar-H),7.11(s,1H,Ar-H),7.03-7.06(m,2H,Ar-H,1H,-CH＝COCH3-),3.99(s,3H,-OCH3),3.94(s,3H,-OCH3),3.79(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,153.1,149.1,148.9,142.5,135.4,132.4,131.3,131.2,129.7,129.6,129.1,126.6,125.1,124.9,122.8,113.5,111.2(2C),56.1,56.0,55.5.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found347.1278.
4-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物4s):
Orange solid,mp 180-182℃.1H-NMR(400MHz,CDCl3)δ8.74(d,J＝8.0Hz,1H,Ar-H),8.18(d,J＝8.0Hz,1H,Ar-H),7.88(d,J＝8.0Hz,1H,Ar-H),7.75(t,J＝8.0Hz,1H,Ar-H),7.51(d,J＝8.0Hz,1H,Ar-H),7.07(s,1H,Ar-H),6.92-6.97(m,2H,Ar-H,1H,-CH＝COCH3-),6.08(s,2H,-OCH2-),3.80(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,153.1,147.9,147.6,142.2,135.4,133.6,131.2(2C),129.6(2C),129.1,126.6,125.1,124.8,124.1,111.0,110.5,108.4,101.5,55.5.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0967.
2-Methoxy-4-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物4t):
Orange solid,mp 155-157℃.1H-NMR(400MHz,CDCl3)δ8.78(d,J＝8.0Hz,1H,Ar-H),8.23(d,J＝8.0Hz,1H,Ar-H),7.94(d,J＝8.0Hz,1H,Ar-H),7.80(t,J＝8.0Hz,1H,Ar-H),7.58(d,J＝8.0Hz,1H,Ar-H),7.13(s,1H,-CH＝COCH3-),6.71(s,2H,Ar-H),3.97(s,3H,-OCH3),3.92(s,6H,2x-OCH3),3.81(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,153.2(3C),142.5,137.9,135.5,135.4,131.4,131.3,129.6,129.4,129.1,126.8,125.1,124.8,110.9,107.5(2C),61.1,56.3(2C),55.6.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found 377.1393.
2-Methoxy-4-(3-nitrophenyl)-1H-phenalen-1-one(化合物4u):
Orange solid,mp 222-224℃.1H-NMR(400MHz,CDCl3)δ8.74(d,J＝8.0Hz,1H,Ar-H),8.40(s,1H,Ar-H),8.35(d,J＝8.0Hz,1H,Ar-H),8.23(d,J＝8.0Hz,1H,Ar-H),7.97(d,J＝8.0Hz,1H,Ar-H),7.85(d,J＝8.0Hz,1H,Ar-H),7.74-7.79(m,2H,Ar-H),7.52(d,J＝8.0Hz,1H,Ar-H),6.83(s,1H,-CH＝COCH3-),3.76(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.4,153.7,148.4,141.5,139.2,136.2,135.6,131.7(2C),129.7,129.6,129.4,128.9,127.3,125.3,125.0,124.9,122.9,109.5,55.5.HRMS(ESI)calcd.for[C20H13NO4+H]+332.0917,found 332.0924.
2-Methoxy-5-phenyl-1H-phenalen-1-one(化合物5o):
Orange solid,mp:105-107℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.3Hz,1H),8.24(d,J＝7.9Hz,1H),8.06(d,J＝1.1Hz,1H),7.92(s,1H),7.80–7.71(m,3H),7.53(dd,J＝8.0,7.5Hz,2H),7.43(t,J＝7.4Hz,1H),6.96(s,1H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ180.1,153.7,140.1,139.9,135.6,132.4,130.5,129.3,129.1,128.9,128.8,128.0,127.3,126.8,123.9,112.5,55.7.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1060.
2-Methoxy-5-(4-methoxyphenyl)-1H-phenalen-1-one(化合物5p):
Orange solid,mp:142-144℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.4Hz,1H),8.24(d,J＝8.1Hz,1H),8.02(s,1H),7.90(s,1H),7.78(t,J＝7.7Hz,1H),7.68(d,J＝8.6Hz,2H),7.06(d,J＝8.6Hz,2H),6.97(s,1H),3.98(s,3H),3.90(s,3H).13C NMR(100MHz,CDCl3)δ180.1,159.7,153.6,139.6,135.5,132.5,130.3,129.2,128.8,128.7,128.4,127.3,126.0,123.6,114.6,114.5,112.5,55.7,55.5.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1172.
5-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物5q):
Orange solid,mp:162-164℃.1H NMR(400MHz,CDCl3)δ8.68(dd,J＝7.4,1.0Hz,1H),8.21(d,J＝7.4Hz,1H),7.96(d,J＝1.3Hz,1H),7.87(d,J＝1.2Hz,1H),7.75(t,J＝7.7Hz,1H),7.37(d,J＝8.7Hz,1H),6.94(s,1H),6.65(d,J＝2.3Hz,1H),6.62(s,1H),3.96(s,3H),3.89(s,3H),3.85(s,3H).13C NMR(100MHz,CDCl3)δ180.2,160.9,157.7,153.5,137.5,135.4,132.3,131.8,131.4,130.2,129.3,128.9,127.6,126.9,123.5,122.4,112.9,105.0,99.2,55.7,55.6,55.5.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found347.1285.
5-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物5r):
Orange solid,mp:153-155℃.1H NMR(400MHz,CDCl3)δ8.68(d,J＝7.4Hz,1H),8.24(d,J＝7.9Hz,1H),8.01(s,1H),7.89(s,1H),7.78(t,J＝7.7Hz,1H),7.27(dd,J＝16.2,6.6Hz,2H),7.02(d,J＝8.4Hz,1H),6.97(s,1H),4.02(s,3H),3.98(s,3H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ180.0,153.6,149.5,149.3,139.8,135.4,132.9,132.4,130.3,129.2,128.8,128.7,127.3,126.1,123.7,119.8,112.4,111.8,110.6,56.1,56.1,55.7.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1270.
5-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物5s):
Orange solid,mp:178-180℃.1H NMR(400MHz,CDCl3)δ8.61(d,J＝7.3Hz,1H),8.16(d,J＝7.9Hz,1H),7.91(d,J＝1.2Hz,1H),7.78(d,J＝1.2Hz,1H),7.72(t,J＝7.7Hz,1H),7.18-7.17(m,2H),6.92(d,J＝7.8Hz,1H),6.89(s,1H),6.04(s,2H),3.96(s,3H).13CNMR(100MHz,CDCl3)δ180.0,153.6,148.5,147.7,139.6,135.4,134.3,132.4,130.3,129.2,128.7,127.2,126.1,123.6,120.9,112.4,108.8,107.7,101.4,55.6.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0964.
2-Methoxy-5-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物5t):
Orange solid,mp:159-161℃.1H NMR(400MHz,CDCl3)δ8.65(dd,J＝7.4,0.9Hz,1H),8.23(d,J＝7.5Hz,1H),7.99(d,J＝1.4Hz,1H),7.84(d,J＝1.4Hz,1H),7.76(t,J＝7.7Hz,1H),6.94(s,1H),6.90(s,2H),3.98(s,6H),3.96(s,3H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ180.0,153.7,153.6,140.0,138.2,135.9,135.5,132.3,130.5,129.2,128.8,128.7,127.4,126.5,123.8,112.3,104.6,61.1,56.4,55.7.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found377.1393.
2-Methoxy-5-(3-nitrophenyl)-1H-phenalen-1-one(化合物5u):
Orange solid,mp:227-229℃.1H NMR(400MHz,CDCl3)δ8.71(d,J＝7.2Hz,1H),8.60(s,1H),8.28(d,J＝7.6Hz,2H),8.11(s,1H),8.07(d,J＝7.6Hz,1H),7.91(s,1H),7.82(dd,J＝8.0,7.6Hz,1H),7.70(dd J＝8.0,7.6Hz,1H),6.97(s,1H),3.99(s,3H).13C NMR(100MHz,CDCl3)δ179.8,153.9,148.9,141.8,137.3,135.7,133.1,132.2,131.2,130.1,129.5,129.3,127.7,127.7,127.0,124.4,122.7,122.1,111.9,55.7.HRMS(ESI)calcd.for[C20H13NO4+H]+332.0917,found332.0921.
2-Methoxy-6-phenyl-1H-phenalen-1-one(化合物6o):
Orange solid,mp 107-109℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.3Hz,1H),8.28(d,J＝8.2Hz,1H),7.83–7.60(m,2H),7.51(m,6H),6.94(s,1H),3.98(s,3H).13C NMR(100MHz,CDCl3)δ180.1,153.2,142.1,139.5,134.1,130.8,130.5,130.3(2C),129.6,128.9,128.4(2C),127.8(2C),127.5,126.8,124.9,112.7,55.6.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1060.
2-Methoxy-6-(4-methoxyphenyl)-1H-phenalen-1-one(化合物6p):
Orange solid,mp 139-141℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.3Hz,1H),8.32(d,J＝8.3Hz,1H),7.73(d,J＝7.9Hz,1H),7.69(d,J＝7.8Hz,1H),7.50(d,J＝7.3Hz,1H),7.43(d,J＝8.3Hz,2H),7.06(d,J＝8.3Hz,2H),6.94(s,1H),3.98(s,3H),3.91(s,3H).13C NMR(100MHz,CDCl3)δ180.1,159.5,153.1,141.9,134.2,131.8,131.4(2C),130.8,130.7,129.6,129.1,127.7,127.1,126.7,124.9,113.9(2C),112.7,55.6,55.4.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1172.
6-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物6q):
Orange solid,mp 168-170℃.1H NMR(400MHz,CDCl3)δ8.69(d,J＝7.3Hz,1H),8.01(d,J＝8.3Hz,1H),7.71–7.58(m,2H),7.45(d,J＝7.3Hz,1H),7.22–7.12(m,1H),6.91(s,1H),6.67–6.55(m,2H),3.95(s,3H),3.90(s,3H),3.67(s,3H).13C NMR(100MHz,CDCl3)δ180.1,161.1,158.0,153.1,139.0,134.6,132.4,131.3,130.6,129.5,129.1,128.6,127.3,126.4,124.7,120.9,112.8,104.6,98.8,55.6,55.5(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found347.1285.
6-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物6r):
Orange solid,mp 150-152℃.1H NMR(400MHz,CDCl3)δ8.73(dd,J＝7.3,0.9Hz,1H),8.33(dd,J＝8.3,0.9Hz,1H),7.77–7.69(m,1H),7.68(d,J＝7.4Hz,1H),7.51(d,J＝7.3Hz,1H),7.08–6.98(m,3H),6.93(s,1H),3.98(s,6H),3.92(s,3H).13C NMR(100MHz,CDCl3)δ180.0,153.1,149.0,148.8,142.0,134.1,132.2,130.7,130.7,129.6,128.9,127.7,127.3,126.8,124.9,122.8,113.6,112.7,111.1,56.0(2C),55.6.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1270.
6-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物6s):
Orange solid,mp 180-182℃.1H NMR(400MHz,CDCl3)δ8.73(d,J＝7.3Hz,1H),8.32(d,J＝8.3Hz,1H),7.72(t,J＝7.8Hz,1H),7.66(d,J＝7.3Hz,1H),7.47(d,J＝7.3Hz,1H),7.06–6.88(m,4H),6.07(s,2H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ180.0,153.1,147.7,147.5,141.7,134.0,133.3,130.8,130.6,129.6,128.9,127.7,127.4,126.8,124.9,123.9,112.6,110.7,108.3,101.3,55.6.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0964.
2-Methoxy-6-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物6t):
Orange solid,mp 155-157℃.1H NMR(400MHz,CDCl3)δ8.75–8.68(m,1H),8.35–8.28(m,1H),7.77–7.69(m,1H),7.67(d,J＝7.4Hz,1H),7.51(d,J＝7.3Hz,1H),6.92(s,1H),6.69(s,2H),3.97(s,3H),3.95(s,3H),3.89(s,6H).13C NMR(100MHz,CDCl3)δ180.0,153.2,153.1(2C),142.1,137.9,135.1,134.0,130.8,130.6,129.6,128.8,127.6,127.5,126.9,124.8,112.6,107.7(2C),61.0,56.3(2C),55.6.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found377.1393.
2-Methoxy-6-(3-nitrophenyl)-1H-phenalen-1-one(化合物6u):
Orange solid,mp 222-224℃.1H NMR(400MHz,CDCl3)δ8.76(d,J＝7.3Hz,1H),8.38(s,1H),8.35(d,J＝8.4Hz,1H),8.14(d,J＝8.2Hz,1H),7.84(d,J＝7.5Hz,1H),7.74(dt,J＝17.1,8.7Hz,3H),7.54(d,J＝7.3Hz,1H),6.94(s,1H),4.00(s,3H).13C NMR(100MHz,CDCl3)δ179.9,153.5,148.4,141.2,138.9,136.2,132.9,131.0,130.0,129.7,129.6,129.4,128.8,128.6,128.2,127.5,124.9,122.8,112.3,55.7.HRMS(ESI)calcd.for[C20H13NO4+H]+332.0917,found332.0921.
2-Methoxy-7-phenyl-1H-phenalen-1-one(化合物7o):
Orange viscousness.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.6Hz,1H),7.93(d,J＝8.5Hz,1H),7.71(d,J＝7.6Hz,1H),7.66(d,J＝7.0Hz,1H),7.56–7.41(m,6H),6.92(s,1H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ179.8,153.3,148.2,139.5,130.4,130.2(2C),129.2,128.6,128.4(2C),128.3(2C),128.1(2C),127.9,126.8,125.0,112.8,55.6.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1063.
2-Methoxy-7-(4-methoxyphenyl)-1H-phenalen-1-one(化合物7p):
Orange solid,mp 169-171℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.6Hz,1H),7.99(d,J＝8.2Hz,1H),7.70(d,J＝7.7Hz,1H),7.67(d,J＝6.9Hz,1H),7.51(dd,J＝8.5,7.1Hz,1H),7.48–7.42(m,2H),7.10–7.04(m,2H),6.93(s,1H),3.98(s,3H),3.91(s,3H).13CNMR(100MHz,CDCl3)δ179.9,159.7,153.2,148.1,131.8,131.5(2C),130.5,130.3,129.3,128.3,128.3,128.1,128.1,126.7,125.0,113.9(2C),112.8,55.6,55.4.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1172.
7-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物7q):
Orange solid,mp 169-171℃.1H NMR(400MHz,CDCl3)δ8.73(d,J＝7.6Hz,1H),7.69(dd,J＝8.0,8.1Hz,2H),7.62(d,J＝7.0Hz,1H),7.43(t,J＝7.8Hz,1H),7.18(d,J＝8.7Hz,1H),6.90(s,1H),6.64(d,J＝6.2Hz,1H),6.63(s,1H),3.95(s,3H),3.90(s,3H),3.68(s,3H).13C NMR(100MHz,CDCl3)δ180.0,161.3,157.9,153.1,145.3,132.4,131.1,130.4,129.2,129.1,128.4(2C),128.2,126.4,124.8,120.8,112.8,104.5,98.8,55.6,55.5(2C).HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1274.
7-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物7r):
Orange solid,mp 197-199℃.1H NMR(400MHz,CDCl3)δ8.74(d,J＝7.5Hz,1H),8.01(d,J＝8.2Hz,1H),7.72(d,J＝7.5Hz,1H),7.68(d,J＝5.6Hz,1H),7.53(d,J＝7.1Hz,1H),7.04(t,J＝7.5Hz,3H),6.94(s,1H),3.99(s,6H),3.93(s,2H).13C NMR(100MHz,CDCl3)δ179.8,153.2,149.2,148.8,148.2,132.1,130.5,130.3,129.3,128.4,128.3,128.1(2C),126.7,125.0,122.9,113.5,112.8,111.0,56.0(2C),55.6.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1277.
7-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物7s):
Brown solid,mp 90-92℃.1H NMR(400MHz,CDCl3)δ8.71(d,J＝7.6Hz,1H),7.99(d,J＝8.6Hz,1H),7.67(t,J＝7.6Hz,2H),7.53–7.44(m,1H),6.96(t,J＝12.6Hz,4H),6.07(s,2H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ179.8,153.2,147.9,147.7,147.7,133.2,130.5,130.3,129.3,128.4,128.4,128.1,127.9,126.8,125.0,124.1,112.8,110.7,108.3,101.4,55.6.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0960.
2-Methoxy-7-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物7t):
Orange solid,mp 223-225℃.1H NMR(400MHz,CDCl3)δ8.73(dd,J＝7.6,1.5Hz,1H),8.01(d,J＝8.6Hz,1H),7.73(d,J＝7.6Hz,1H),7.68(d,J＝7.0Hz,1H),7.53(t,J＝7.8Hz,1H),6.94(s,1H),6.71(s,2H),3.98(s,3H),3.96(s,3H),3.90(s,6H).13C NMR(100MHz,CDCl3)δ179.8,153.2,153.1(2C),148.2,138.0,135.0,130.4,130.3,129.3,128.5,128.4,127.9(2C),126.9,125.0,112.8,107.6(2C),61.0,56.3(2C),55.6.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found 377.1373.
2-Methoxy-7-(3-nitrophenyl)-1H-phenalen-1-one(化合物7u):
Orange solid,mp 222-224℃.1H NMR(400MHz,CDCl3)δ8.75(d,J＝7.6Hz,1H),8.38(m,2H),7.85(d,J＝7.6Hz,1H),7.80–7.75(m,1H),7.73(d,J＝7.4Hz,2H),7.70(d,J＝7.1Hz,1H),7.55(dd,J＝8.4,7.3Hz,1H),6.94(s,1H),3.99(s,3H).13C NMR(100MHz,CDCl3)δ179.7,153.3,148.2,144.9,141.1,136.1,130.2,129.9,129.5,129.5,129.4,128.7,128.2,127.6,126.7,125.0,124.9,123.1,112.8,55.7.HRMS(ESI)calcd.for[C20H13NO4+H]+332.0917,found332.0914.
2-Methoxy-8-phenyl-1H-phenalen-1-one(化合物8o):
Orange solid,mp:110-112℃.1H NMR(400MHz,CDCl3)δ8.91(d,J＝1.9Hz,1H),8.34(s,1H),7.90(d,J＝8.1Hz,1H),7.77(d,J＝7.8Hz,2H),7.61(d,J＝6.9Hz,1H),7.57–7.48(m,3H),7.42(t,J＝7.3Hz,1H),6.86(d,J＝3.6Hz,1H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ180.1,153.4,139.9,139.5,132.9,132.4,129.9,129.7,129.4,129.2,129.1,128.2,128.1,127.5,127.3,123.7,112.5,55.7.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1060.
2-Methoxy-8-(4-methoxyphenyl)-1H-phenalen-1-one(化合物8p):
Orange solid,mp:160-162℃.1H NMR(400MHz,CDCl3)δ8.88(d,J＝1.7Hz,1H),8.29(d,J＝1.4Hz,1H),7.88(d,J＝8.1Hz,1H),7.70(d,J＝8.6Hz,2H),7.59(d,J＝6.9Hz,1H),7.51(dd,J＝8.0,7.3Hz,1H),7.02(d,J＝8.7Hz,2H),6.86(s,1H),3.95(s,3H),3.87(s,3H).13C NMR(100MHz,CDCl3)δ180.1,159.8,153.4,139.4,132.5,132.2,131.9,129.6,129.3,128.9,128.6,128.0,127.2,123.3,114.5,112.5,55.7,55.4.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1172.
8-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物8q):
Orange solid,mp:163-165℃.1H NMR(400MHz,CDCl3)δ8.86(d,J＝1.6Hz,1H),8.30(d,J＝1.5Hz,1H),7.88(d,J＝8.1Hz,1H),7.60(d,J＝7.0Hz,1H),7.54–7.49(m,1H),7.37(d,J＝8.0Hz,1H),6.88(s,1H),6.62(d,J＝2.4Hz,1H),6.59(s,1H),3.95(s,3H),3.87(s,3H),3.82(s,3H).13C NMR(100MHz,CDCl3)δ180.2,160.9,157.6,153.4,137.4,135.6,132.8,132.1,131.6,129.4,128.9,128.9,127.9,126.9,123.3,121.9,112.5,104.9,98.9,55.6,55.5.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1285.
8-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物8r):
Orange solid,mp:190-192℃.1H NMR(400MHz,CDCl3)δ8.89(s,1H),8.32(s,1H),7.92(d,J＝8.1Hz,1H),7.62(d,J＝7.0Hz,1H),7.56(t,J＝7.6Hz,1H),7.33(d,J＝8.3Hz,1H),7.28(s,1H),7.00(d,J＝8.3Hz,1H),6.89(s,1H),4.02(s,3H),3.97(s,3H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ180.1153.4,149.6,149.4,139.7,132.5,132.5,132.4,129.6,129.3,128.9,128.1,127.2,123.5,120.1,112.5,111.8,110.7,56.2,56.0,55.6.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1270.
8-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物8s):
Brown solid,mp:100-102℃.1H NMR(400MHz,CDCl3)δ8.84(d,J＝1.7Hz,1H),8.27(d,J＝1.5Hz,1H),7.89(d,J＝8.2Hz,1H),7.61(d,J＝7.0Hz,1H),7.57–7.51(m,1H),7.25(d,J＝1.8Hz,1H),7.23(s,1H),6.93(d,J＝8.5Hz,1H),6.87(s,1H),6.04(s,2H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ180.1,153.4,148.5,147.8,139.6,133.8,132.5,132.4,129.7,129.6,129.3,129.0,128.1,127.3,123.5,121.3,112.5,108.8,107.9,101.4,55.7.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0964.
2-Methoxy-8-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物8t):
Orange solid,mp:167-169℃.1H NMR(400MHz,CDCl3)δ8.83(s,1H),8.30(s,1H),7.93(d,J＝8.0Hz,1H),7.62(d,J＝6.8Hz,1H),7.56(t,J＝7.5Hz,1H),6.91(s,2H),6.87(s,1H),3.98(s,6H),3.96(s,3H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ180.1,153.7(2C),153.4,139.9,138.2,135.5,132.9,132.4,129.7,129.6,129.3,129.2,128.1,127.4,123.6,112.5,104.8(2C),61.0,56.4,55.7.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found 377.1393.
2-Methoxy-8-(3-nitrophenyl)-1H-phenalen-1-one(化合物8u):
Orange solid,mp:219-221℃.1H NMR(400MHz,CDCl3)δ8.97(d,J＝1.8Hz,1H),8.66(s,1H),8.46(d,J＝1.7Hz,1H),8.30(dd,J＝8.2,1.3Hz,1H),8.15(d,J＝7.7Hz,1H),8.00(d,J＝8.1Hz,1H),7.75–7.69(m,2H),7.67–7.61(m,1H),6.95(s,1H),4.00(s,3H).13CNMR(100MHz,CDCl3)δ179.9,153.5,148.9,141.4,137.4,133.5,133.2,132.6,130.1(2C),129.8,129.5,129.3,128.3,127.9,124.3,122.9,122.3,112.6,55.8.HRMS(ESI)calcd.for[C20H13NO4+H]+332.0917,found 332.0921.
2-Methoxy-9-phenyl-1H-phenalen-1-one(化合物9o):
Orange viscousness,1H-NMR(400MHz,CDCl3)δ8.06(d,J＝8.0Hz,1H,Ar-H),7.80(d,J＝8.0Hz,1H,Ar-H),7.57(d,J＝8.0Hz,1H,Ar-H),7.49(d,J＝8.0Hz,2H,Ar-H),7.28-7.35(m,5H,Ar-H),6.76(s,1H,-CH＝COCH3-),3.79(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,153.6,148.2,142.8,134.3,131.6,131.5,129.4,129.1,128.8,128.3(2C),127.9(2C),127.1,126.7,125.8,125.4,111.4,55.6.HRMS(ESI)calcd.for[C20H14O2+H]+287.1067,found 287.1062.
2-Methoxy-9-(4-methoxyphenyl)-1H-phenalen-1-one(化合物9p):
Orange solid,mp 169-171℃.1H-NMR(400MHz,CDCl3)δ7.97(d,J＝8.4Hz,1H,Ar-H),7.72(d,J＝8.0Hz,1H,Ar-H),7.50(d,J＝6.8Hz,1H,Ar-H),7.38-7.44(m,2H,Ar-H),7.22(d,J＝8.8Hz,2H,Ar-H),6.86(d,J＝8.4Hz,2H,Ar-H),6.69(s,1H,-CH＝COCH3-),3.74(brs,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,159.0,153.6,147.9,134.8,134.2,131.7,131.3,129.5(2C),129.3,129.0,128.6,126.5,125.6,125.5,113.8(2C),111.3,55.5,55.3.HRMS(ESI)calcd.for[C21H16O3+H]+317.1172,found 317.1173.
9-(2,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物9q):
Orange solid,mp 169-171℃.1H-NMR(400MHz,CDCl3)δ8.16(d,J＝8.0Hz,1H,Ar-H),7.89(d,J＝8.0Hz,1H,Ar-H),7.65(d,J＝8.0Hz,1H,Ar-H),7.55-7.58(m,2H,Ar-H),7.07(d,J＝8.0Hz,1H,Ar-H),6.84(s,1H,-CH＝COCH3-),6.56-6.60(m,2H,Ar-H),3.88(s,3H,-OCH3),3.87(s,3H,-OCH3),3.67(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,160.6,157.7,153.4,144.1,134.3,131.9,131.6,129.2,128.9,128.9,128.7,126.8,126.4,125.3,124.8,111.2,104.6,98.7,55.6,55.5,55.4.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1278.
9-(3,4-Dimethoxyphenyl)-2-methoxy-1H-phenalen-1-one(化合物9r):
Orange solid,mp 197-199℃.1H-NMR(400MHz,CDCl3)δ8.15(d,J＝8.0Hz,1H,Ar-H),7.90(d,J＝8.0Hz,1H,Ar-H),7.67(d,J＝8.0Hz,1H,Ar-H),7.57-7.61(m,2H,Ar-H),6.91-6.96(m,3H,Ar-H),6.86(s,1H,-CH＝COCH3-),3.94(s,3H,-OCH3),3.89(s,3H,-OCH3),3.87(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,153.7,148.8,148.4,148.0,135.4,134.2,131.7,131.5,129.4,129.1,128.7,126.7,125.8,125.5,120.3,111.6,111.3,111.2,56.0,55.9,55.6.HRMS(ESI)calcd.for[C22H18O4+H]+347.1278,found 347.1278.
9-(Benzo[d][1,3]dioxol-5-yl)-2-methoxy-1H-phenalen-1-one(化合物9s):
Brown solid,mp 90-92℃.1H-NMR(400MHz,CDCl3)δ8.14(d,J＝8.0Hz,1H,Ar-H),7.88(d,J＝8.0Hz,1H,Ar-H),7.67(d,J＝8.0Hz,1H,Ar-H),7.56-7.59(m,2H,Ar-H),6.90(d,J＝8.0Hz,1H,Ar-H),6.82-6.85(m,2H,Ar-H,1H,-CH＝COCH3-),6.00(s,2H,-OCH2-),3.89(s,3H,-OCH3).13C-NMR(100MHz,CDCl3)δ179.9,153.6,147.8,147.6,147.0,136.5,134.3,131.6,131.5,129.4,129.1,128.7,126.7,125.8,125.4,121.3,111.4,109.2,108.4,101.0,55.6.HRMS(ESI)calcd.for[C21H14O4+H]+331.0965,found 331.0967.
2-Methoxy-9-(3,4,5-trimethoxyphenyl)-1H-phenalen-1-one(化合物9t):
Orange solid,mp 223-225℃.1H-NMR(400MHz,CDCl3)δ8.16(d,J＝8.0Hz,1H,Ar-H),7.91(d,J＝8.0Hz,1H,Ar-H),7.70(d,J＝8.0Hz,1H,Ar-H),7.59-7.61(m,2H,Ar-H),6.87(s,1H,-CH＝COCH3-),6.54(s,2H,Ar-H),3.91(s,3H,-OCH3),3.90(s,3H,-OCH3),3.83(s,6H,2x-OCH3).13C-NMR(100MHz,CDCl3)δ179.7,153.6,153.2(2C),148.0,138.5,137.2,134.2,131.6,131.3,129.5,129.1,128.7,126.8,125.8,125.3,111.4,104.8(2C),61.0,56.0(2C),55.6.HRMS(ESI)calcd.for[C23H20O5+H]+377.1384,found 377.1388.
实施例4目标化合物4h-n,5h-n,6h-n,7h-n,8h-n，4o-u,5o-u,6o-u,7o-u,8o-u的合成第二方案
其中化合物4h-n,5h-n,6h-n,7h-n,8h-n可以经过原料5-8(5、6、7或8位溴取代)，先合成中间体4aa-8aa，然后再经过铃木偶联反应得到目标化合物；化合物4o-u,5o-u,6o-u,7o-u,8o-u可由中间体4aa-8aa经过甲氧基化得到中间体4ab-8ab，再由中间体4ab-8ab经过铃木偶联反应得到目标化合物。中间体理化数据如下：4-Bromo-2-hydroxy-1H-phenalen-1-one(化合物4aa):
Red solid,mp:275-277℃.1H NMR(400MHz,DMSO-d6)δ10.22(s,1H),8.57(d,J＝7.3Hz,1H),8.45(d,J＝8.1Hz,1H),7.97(d,J＝8.8Hz,1H),7.92(d,J＝7.7Hz,1H),7.87(d,J＝8.8Hz,1H),7.32(s,1H).13C NMR(100MHz,DMSO-d6)δ179.9,152.5,136.9,132.1,131.6,131.3,130.6,128.1,127.9(2C),125.1,124.9,112.9.HRMS(ESI)calcd.for[C13H7BrO2Na]+296.9522,found 296.9520.
4-Bromo-2-methoxy-1H-phenalen-1-one(化合物4ab):
Orange solid,mp:160-162℃,1H NMR(400MHz,CDCl3)δ8.70(d,J＝8.0,1H),8.09(dd,J＝8.0,1.1Hz,1H),7.73–7.69(m,1H),7.65(d,J＝7.6Hz,2H),7.19(s,1H),3.97(s,3H).13C NMR(100MHz,CDCl3)δ179.5,154.1,135.6,131.6,131.5,130.9,129.8,128.5,127.3,127.0,125.8,125.5,110.9,55.8.HRMS(ESI)calcd.for[C14H9BrO2+H]+288.9864,found 288.9869.
5-Bromo-2-hydroxy-1H-phenalen-1-one(化合物5aa):
Red solid,mp:286-288℃.1H NMR(400MHz,DMSO-d6)δ9.94(s,1H),8.55(d,J＝7.2Hz,1H),8.40(d,J＝8.0Hz,1H),8.33(s,1H),8.00(s,1H),7.91(dd,J＝7.2,8.0Hz,1H),7.16(s,1H).13C NMR(100MHz,DMSO-d6)δ180.2,151.8,135.7,133.2,131.6(2C),130.8,130.4,128.7,128.6,122.8,120.8,113.9.HRMS(ESI)calcd.for[C13H7BrO2Na]+296.9522,found 296.9518.
5-Bromo-2-methoxy-1H-phenalen-1-one(化合物5ab):
Orange solid,mp:168-170℃,1H NMR(400MHz,CDCl3)δ8.67(d,J＝7.2Hz,1H),8.11(d,J＝8.0Hz,1H),8.04(s,1H),7.78(dd,J＝7.2,8.0Hz,1H),7.74(s,1H),7.26(s,1H),6.80(s,1H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ179.5,153.8,134.3,132.8,131.3,130.6,130.3,130.1,129.2,127.7,123.0,120.6,110.9,55.7.HRMS(ESI)calcd.for[C14H9BrO2+H]+288.9864,found288.9860.
6-Bromo-2-hydroxy-1H-phenalen-1-one(化合物6aa):
Red solid,mp:273-275℃.1H NMR(400MHz,DMSO-d6)δ9.85(s,1H),8.61(d,J＝7.3Hz,1H),8.57(d,J＝8.2Hz,1H),8.01(d,J＝7.6Hz,1H),7.98(s,1H),7.68(d,J＝7.7Hz,1H),7.14(s,1H).13C NMR(100MHz,DMSO-d6)δ179.9,151.1,134.7,131.9,131.5,130.6,130.2,129.4,129.2,129.0,125.4,123.5,115.0.HRMS(ESI)calcd.for[C13H7BrO2Na]+296.9522,found296.9525.
6-Bromo-2-methoxy-1H-phenalen-1-one(化合物6ab):
Orange solid,mp:159-161℃,1H NMR(400MHz,CDCl3)δ8.69(d,J＝7.2Hz,1H),8.55(d,J＝8.4Hz,1H),7.84–7.76(m,2H),7.41(d,J＝7.7Hz,1H),6.79(s,1H),3.96(s,3H).13C NMR(100MHz,CDCl3)δ179.3,153.2,134.6,131.5,130.9,130.8,129.6,129.1,128.1,127.9,125.8,124.6,112.1,55.7.HRMS(ESI)calcd.for[C14H9BrO2+H]+288.9864,found 288.9868.
7-Bromo-2-hydroxy-1H-phenalen-1-one(化合物7aa):
Red solid,mp:280-282℃.1H NMR(400MHz,DMSO-d6)1H NMR(400MHz,DMSO)δ9.82(s,1H),8.34(d,J＝8.0Hz,1H),8.16(d,J＝8.0Hz,1H),8.11(d,J＝8.5Hz,1H),7.83(d,J＝7.0Hz,1H),7.72(dd,J＝8.0,8.0Hz,1H),7.14(s,1H).13C NMR(100MHz,DMSO-d6)δ180.0,151.0,131.8,131.7,130.9,130.7,130.7,129.8,129.5,128.4,127.5,125.1,115.2.HRMS(ESI)calcd.for[C13H7BrO2Na]+296.9522,found 296.9516.
7-Bromo-2-methoxy-1H-phenalen-1-one(化合物7ab):
Orange solid,mp:173-175℃.1H NMR(400MHz,CDCl3)δ8.41(d,J＝8.0Hz,1H),8.18(d,J＝8.0Hz,1H),7.97(d,J＝8.0Hz,1H),7.62–7.53(m,2H),6.80(s,1H),3.94(s,3H).13C NMR(100MHz,CDCl3)δ179.6,153.2,132.1,131.2,131.0,130.8,129.9,128.8,128.7,128.3,128.1,125.6,112.3,55.7.HRMS(ESI)calcd.for[C14H9BrO2+H]+288.9864,found 288.9861.
8-Bromo-2-hydroxy-1H-phenalen-1-one(化合物8aa):
Red solid,mp:264-266℃.1H NMR(400MHz,DMSO-d6)δ9.83(s,1H),8.68(d,J＝2.0Hz,1H),8.48(d,J＝2.0Hz,1H),7.99(d,J＝8.0Hz,1H),7.81(d,J＝7.2Hz,1H),7.73-7.61(m,1H),7.16(s,1H).13C NMR(100MHz,DMSO-d6)δ179.4,150.9,137.6,133.7,132.1,130.3,130.2,129.2,129.0,128.5,122.6,120.5,115.5.HRMS(ESI)calcd.for[C13H7BrO2Na]+296.9522,found296.9516
8-Bromo-2-methoxy-1H-phenalen-1-one(化合物8ab):
Orange solid,mp:170-172℃.1H NMR(400MHz,CDCl3)δ8.63(d,J＝1.7Hz,1H),8.25(d,J＝1.7Hz,1H),7.73(d,J＝8.2Hz,1H),7.59(d,J＝6.9Hz,1H),7.55–7.50(m,1H),6.81(s,1H),3.93(s,3H).13C NMR(100MHz,CDCl3)δ178.9,153.1,136.8,133.3,133.2,130.4,129.5,128.3,128.2,128.0,123.0,121.2,112.5,55.7.HRMS(ESI)calcd.for[C14H9BrO2+H]+288.9864,found288.9866.
实施例5苯基萘嵌苯酮及其衍生物的抗病毒活性
抗病毒活性测试(以烟草花叶病毒TMV为例)
1、抗病毒钝化活性实验：
幼苗长到5-7片真叶时，取健康、生长旺盛、叶片大小一致的植株。将待测化合物与TMV病毒先共孵育30分钟。然后以叶脉为界，在左、右半叶上分别接种含有TMV和化合物的培养液及对照液(N,N-二甲基甲酰胺，水，0.1％TW-80，TMV培养液)。每株接种4个叶片，每组重复3株。3天后统计枯斑数数目，按下式计算抑制率：
抑制率％＝[(对照平均每叶枯斑数-处理平均每叶枯斑数)/对照平均每叶枯斑数]x100％。
实验结果如表2所示。
表2、化合物4a-9t的体内抗病毒活性测试结果(浓度：500μg/mL)a
a活性测试由三次实验结果平均值。
从表中的数据可以看出:本发明的苯基萘嵌苯酮化合物均具有较好的抗病毒钝化活性，其中，化合物4b、4g、4q、6b、6i、6o、7c、8m、8o、8r、9a、9d、9r抗病毒钝化活性均在50％以上，6b、6i和9d的活性最强，说明在萘嵌苯酮母核2-位羟基取代的衍生物中，苯环的对位为甲氧基时，抗病毒活性最强；在萘嵌苯酮母核2-位没有取代的衍生物中，苯环的3,4-位都为甲氧基时，抗病毒活性最强。
根据化合物抗病毒钝化作用的效果以及其它理化性质(溶解性等)，我们选择了化合物4g,6b,6i,6o,7c,8m,8o,9a,9d进一步测试其对病毒的治疗及保护活性。
2、抗病毒治疗活性实验：
幼苗长到5-7片真叶时，取健康、生长旺盛、叶片大小一致的植株。将TMV病毒先接种于烟草生长6小时。然后将叶片用水清洗，自然晾干，以叶脉为界，在左、右半叶上分别喷洒化合物的溶液及对照液(N,N-二甲基甲酰胺，水，0.1％TW-80)。每株接种4个叶片，每组重复3株。3天后统计枯斑数数目，按下式计算抑制率：
抑制率％＝[(对照平均每叶枯斑数-处理平均每叶枯斑数)/对照平均每叶枯斑数]x100％。实验结果如表3所示：
结果表明：化合物对病毒的治疗作用相对钝化作用都有所下降，其中化合物6o,7c的治疗作用最佳，说明在萘嵌苯酮母核2-位有甲氧基取代时，6位为苯基取代基时的治疗活性最佳(6o)；在萘嵌苯酮母核2-位没有取代基时，7位为2,4-二甲氧基苯时的治疗活性最佳(7c)；其它位置的取代基活性相对较弱。
3、抗病毒保护活性实验：
幼苗长到5-7片真叶时，取健康、生长旺盛、叶片大小一致的植株。将化合物溶液喷洒于烟草生长12小时。然后将含有TMV病毒的培养液采用叶面摩擦法接种病毒。30分钟后用蒸馏水清洗，每株接种4个叶片，每组重复3株。3天后统计枯斑数数目，按下式计算抑制率：
抑制率％＝[(对照平均每叶枯斑数-处理平均每叶枯斑数)/对照平均每叶枯斑数]x100％。实验结果如表3所示：
表3化合物4g,6b,6i,6o,7c,8m,8o,9a,9d体内抗病毒活性结果(浓度：500μg/mL)
a活性测试由三次实验结果平均值。
结果表明：化合物对病毒的均具有明显的保护作用。
实施例6化合物4a-9t的抗肿瘤活性
以人结肠癌细胞HCT-116、胰腺癌细胞HT-29、人前列腺癌细胞PANC-1、乳腺癌细胞PC-3、乳腺管癌细胞BT-549、乳腺癌细胞MDA-MD-231为例。
实验方法：
将化合物样品用DMSO溶解，细胞用RPMI1640培养基培养。将肿瘤细胞以2-7×104cell/mL浓度接种于96孔板中，在37℃,5％CO2条件下培养24h，加入10μL用培养基稀释后的化合物样品，最终每孔样品的浓度为20μg/mL，每个化合物设置3个重复样本，对照组细胞加入DMSO替换化合物，三个只有培养基而无细胞的孔作为背景对照，继续培养72h后，加入50％的冷的三氯乙酸溶液固定细胞，在4℃保持1h，洗去固定液，晾干。加入100μL含0.4％SRB的1％冰醋酸溶液，染色15min，过量染色剂用1％冰醋酸洗去，晾干。加入10mM Tris缓冲液100μL溶解，在515nm波长下用酶标仪读出吸光值(A)。
细胞抑制率(％)＝(无药细胞对照孔A值平均值-用药孔A值平均值)/无药细胞对照孔A值平均值×100％。
化合物经5个浓度梯度稀释分别加入培养细胞中，重复肿瘤细胞抑制活性实验。测出各浓度下的百分抑制率，用Bliss程序计算其半数抑制浓度(IC50)，结果见表4。
表4化合物4a-9t对癌细胞的作用(IC50,μM)a
a活性测试由三次实验结果平均值得出。
实验结果与讨论：
在针对癌细胞HCT-116的活性实验结果中，化合物6p的活性最强，说明在萘嵌苯酮母核2-位有甲氧基取代时，比其它取代基的活性强(-H,OH等)，且6位芳环为对甲氧基苯基时活性最强。
在针对癌细胞HT-29的活性实验结果中，化合物7c的活性最强，说明在萘嵌苯酮母核2-位无取代基时，比其它取代基的活性强(-OH，-OCH3等)，且7位芳环为2,4-二甲氧基苯基时活性最强。
在针对癌细胞PANC-1的活性实验结果中，化合物4t的活性最强，说明在萘嵌苯酮母核2-位有甲氧基取代时，比其它取代基的活性强(-H,OH等)，且4位芳环为3,4,5-三甲氧基苯基时活性最强。
在针对癌细胞PC-3的活性实验结果中，化合物9c的活性最强，说明在萘嵌苯酮母核2-位无取代基时，比其它取代基的活性强(-OH，-OCH3等)，且9位芳环为2,4,-二甲氧基苯基时活性最强。
在针对癌细胞BT-549的活性实验结果中，化合物6b的活性最强，说明在萘嵌苯酮母核2-位无取代基时，比其它取代基的活性强(-OH，-OCH3等)，且6位芳环为4-甲氧基苯基时活性最强。
在针对癌细胞MDA-MD-231的活性实验结果中，化合物8r的活性最强，说明在萘嵌苯酮母核2-位有甲氧基取代时，比其它取代基的活性强(-H,OH等))，且8位芳环为3,4,-二甲氧基苯基时活性最强。
Claims (10)
1.通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
R1为H、OH、C1-C4烷氧基，优选为H、OH、甲氧基；
Ar为取代或未取代的6-10元芳基或5-10元杂芳基，所述取代基为C1-C6烷基、硝基、氨基、羟基、氰基、C1-C6烷氧基中的一个或多个，或所述芳基或杂芳基的相邻位置的取代基一起组成5-6元杂环基，所述杂环基含有1-3个N、O或S的杂原子。
2.权利要求1的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
Ar为取代或未取代的苯基，所述取代基为C1-C4烷基、硝基、氨基、羟基、氰基、C1-C4烷氧基中的一个或多个，或所述苯基的相邻位置的取代基一起组成5-6元杂环基，所述杂环基含有1-3个O原子。
3.权利要求1或2的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
Ar为取代或未取代的苯基，所述取代基为C1-C4烷基、硝基、C1-C4烷氧基中的一个或多个，或与萘嵌苯酮连接的苯基的对位和邻位一起组成5-6元杂环基，所述杂环基含有1-3个O原子。
4.权利要求1-3的任何一项的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐：
其中，
5.如权利要求1所述的苯基萘嵌苯酮化合物的制备方法，其特征在于，
其中，R为卤素。
6.如权利要求1所述的苯基萘嵌苯酮化合物的制备方法，其特征在于，
其中，R为卤素。
7.药物组合物，包含权利要求1-4任何一项所述的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐和药学上可接受的载体或赋形剂。
8.权利要求1-4任何一项所述的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐或权利要求7所述的药物组合物在制备抗肿瘤药物中的应用。
9.权利要求1-4任何一项所述的通式I或II所示的苯基萘嵌苯酮化合物或其药学上可接受的盐或权利要求7所述的药物组合物在制备抗病毒农药中的应用。
10.权利要求9或10所述的应用，其特征在于，所述的肿瘤为结肠癌、胰腺癌、前列腺癌、乳腺癌、乳腺管癌；所述的病毒为烟草花叶病毒。
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| BRESOLI-OBACH, ROGER等: "9-Aryl-phenalenones: Bioinspired thermally reversible photochromic compounds for photoswitching applications in the pico-to milliseconds range", DYES AND PIGMENTS, vol. 186, pages 109060 * |
| DONG LIAOBIN等: "Chemical constituents from the aerial parts of Musella lasiocarpa", NATURAL PRODUCTS AND BIOPROSPECTING, vol. 1, no. 1, pages 41 * |
| OTALVARO, FELIPE等: "Synthesis of [phenyl-13C6]lachnanthocarpone and other 13C-labeled phenylphenalenones", JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, vol. 47, no. 2, pages 147 - 159 * |
| WANG MINGZHONG等: "Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer", JOURNAL OF NATURAL PRODUCTS, vol. 81, no. 1, pages 99 - 102 * |
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