CN104355979B - 4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法 - Google Patents

4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法 Download PDF

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CN104355979B
CN104355979B CN201410502244.XA CN201410502244A CN104355979B CN 104355979 B CN104355979 B CN 104355979B CN 201410502244 A CN201410502244 A CN 201410502244A CN 104355979 B CN104355979 B CN 104355979B
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tetralone
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王强
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Ningbo Institute of Technology of ZJU
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Abstract

本发明公开了4-羟基-8-（2，3-二羟基丙氧基）-1-四氢萘酮及合成方法，4-羟基-8-（2，3-二羟基丙氧基）-1-四氢萘酮是4,8-二羟基-1-四氢萘酮的衍生物，熔点420-422K，溶于水、乙醇、丙酮及氯仿，为外消旋体，具有显著抑制植物种子萌发和幼苗生长的作用。其合成方法工艺简单，产物纯度高，达到99.08%，反应总收率为32-43%。

Description

4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法
技术领域
本发明涉及4,8-二羟基-1-四氢萘酮的衍生物，具体涉及4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法。
背景技术
4,8-二羟基-1-四氢萘酮(4,8-DHT)，化学名4,8-dihydroxy-1-tetralone，无色细簇针状结晶,其中4位与羟基相连的碳为一个手性碳，具有抗肿瘤、抗真菌、降血糖及免疫调节等作用。4,8-DHT的左旋对映体(–)被称为regiolone，右旋对映体(+)被称为isosclerone，4,8-DHT还有外消旋体。Regiolone最早是从青核桃中鉴定出的，可用于治疗皮肤瘙痒及痛等病症。Isosclerone最早是从Sclerotiniasclerotium中分离鉴定出，后来从一些真菌中也分离出了该化合物，它能引起葡萄灰色斑点病。山核桃中就发现外消旋体的4,8-DHT。
发明内容
本发明所要解决的技术问题是提供一种4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法，其具有显著抑制植物种子萌发和幼苗生长的作用。
本发明解决上述技术问题所采用的技术方案为：4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮，其分子式为C13H16O5，结构式为：熔点420-422K，溶于水、乙醇、丙酮及氯仿，为外消旋体，[α]20 D＝±0°(c1.3,CH2Cl2)。
4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的合成方法，步骤如下：
将0.37g4,8-二苯甲酰酯基-1-四氢萘酮溶于12-15ml甲醇，加0.4-0.6g碳酸铯搅拌均匀，室温反应2h，除去甲醇，每次20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用45-60ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:8的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干燥，得到淡黄色粒状晶体：4-苯甲酰基-8-羟基-1-四氢萘酮，其分子式为C17H14O4；将上述C17H14O4溶于10ml无水四氢呋喃，加入1.2当量的氢化钠，室温下反应30min，再加入3.5-5ml环氧溴丙烷，升温至50℃反应30-45min，氯化铵淬灭反应，减压浓缩至干，用体积比1：1的乙酸乙酯和水混合液25ml萃取，有机相用45-60ml饱和食盐水除盐，再加50g无水硫酸钠除水后，减压浓缩至干，得淡黄色粒状晶体：4-苯甲酰基-8-(2-环氧基丙氧基)-1-四氢萘酮，其分子式为C20H18O5；将上述C20H18O5溶于7.5-10ml甲醇，加入1当量的碳酸铯，室温下反应30min，除去甲醇，每次15-20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用25-30ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:5的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干，得到：4-羟基-8-(2-环氧丙氧基)-1-四氢萘酮，其分子式为C13H14O4；将上述C13H14O4溶于5-7ml水，在70℃反应24h，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用乙酸乙酯洗脱，洗脱液减压浓缩至干，得到4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的淡黄色针状晶体。采用高效液相色谱法测定，纯度达到99.08％。
与现有技术相比，本发明的优点在于4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮及合成方法，4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮是4,8-二羟基-1-四氢萘酮的衍生物，熔点420-422K，溶于水、乙醇、丙酮及氯仿，为外消旋体，具有显著抑制植物种子萌发和幼苗生长的作用。其合成方法工艺简单，产物纯度高，达到99.08％，反应总收率为32-43％。
附图说明
图1为本发明的合成示意图。
具体实施方式
以下结合附图实施例对本发明作进一步详细描述。
实施例1
一种以4,8-二苯甲酰酯基-1-四氢萘酮为原料合成外消旋4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的方法：将0.37g4,8-二苯甲酰酯基-1-四氢萘酮溶于12-15ml甲醇，加0.4-0.6g碳酸铯搅拌均匀，室温反应2h，除去甲醇，每次20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用45-60ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:8的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干燥，得到淡黄色粒状晶体：4-苯甲酰基-8-羟基-1-四氢萘酮，其分子式为C17H14O4；将上述C17H14O4溶于10ml无水四氢呋喃，加入1.2当量的氢化钠，室温下反应30min，再加入3.5-5ml环氧溴丙烷，升温至50℃反应30-45min，氯化铵淬灭反应，减压浓缩至干，用体积比1：1的乙酸乙酯和水混合液25ml萃取，有机相用45-60ml饱和食盐水除盐，再加50g无水硫酸钠除水后，减压浓缩至干，得淡黄色粒状晶体：4-苯甲酰基-8-(2-环氧基丙氧基)-1-四氢萘酮，其分子式为C20H18O5；将上述C20H18O5溶于7.5-10ml甲醇，加入1当量的碳酸铯，室温下反应30min，除去甲醇，每次15-20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用25-30ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:5的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干，得到：4-羟基-8-(2-环氧丙氧基)-1-四氢萘酮，其分子式为C13H14O4；将上述C13H14O4溶于5-7ml水，在70℃反应24h，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用乙酸乙酯洗脱，洗脱液减压浓缩至干，得到4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的淡黄色针状晶体。反应总收率为32-43％，采用高效液相色谱法测定，得到纯度达到99.81％。熔点420-422K，溶于水、乙醇、丙酮及氯仿，为外消旋体，[α]20 D＝±0°(c1.3,CH2Cl2)。
实施例2
将获得的4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮配置成0.01mM、0.05mM、0.1mM和0.5mM的处理液作对莴苣种子萌发抑制实验，取100粒测试物种种子均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。种子萌发以胚根突破种皮为标准，第四天和第七天记录莴苣种子发芽数。0.01mM处理液可以使莴苣种子发芽势降低51％，发芽率降低59％；0.1mM和0.5mM处理液种子不发芽。用0.01mM、0.05mM、0.1mM和0.5mM的处理液作对莴苣实生苗生长抑制实验，取胚根突破种皮种子100粒均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加入10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。每隔一天从发芽盒中随机取5粒种子测其胚根、胚芽长度及鲜重，共测6次。0.01mM处理液可以使莴苣实生苗胚根长度降低39％、胚芽长度降低21％、鲜重降低35％，0.1mM和0.5mM处理液实生苗无生长迹象。
实施例3
将获得的4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮配置成0.01mM、0.05mM、0.1mM和0.5mM的处理液作对萝卜种子萌发抑制实验，取100粒测试物种种子均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。种子萌发以胚根突破种皮为标准，第四天和第十天记录萝卜种子发芽数。0.01mM处理液可以使萝卜种子发芽势降低35％，发芽率降低44％；0.5mM处理液种子不发芽。用0.01mM、0.05mM、0.1mM和0.5mM的处理液作对萝卜实生苗生长抑制实验，取胚根突破种皮种子100粒均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加入10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。每隔一天从发芽盒中随机取5粒种子测其胚根、胚芽长度及鲜重，共测6次。0.01mM处理液可以使萝卜实生苗胚根长度降低32％、胚芽长度降低19％、鲜重降低24％；0.5mM处理液实生苗无生长迹象。
实施例4
将获得的4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮配置成0.01mM、0.05mM、0.1mM和0.5mM的处理液作对黄瓜种子萌发抑制实验，取100粒测试物种种子均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。种子萌发以胚根突破种皮为标准，第四天和第八天记录黄瓜种子发芽数。0.01mM处理液可以加速黄瓜种子萌发过程，种子发芽势增加12％，种子发芽率数据无变化；0.5mM处理液显著抑制黄瓜种子萌发过程，种子发芽势降低82％，种子发芽率降低90％。用0.01mM、0.05mM、0.1mM和0.5mM的处理液作对黄瓜实生苗生长抑制实验，取胚根突破种皮种子100粒均匀摆放在铺有两层滤纸、大小15×20cm发芽盒，加入10ml不同浓度处理液(对照组为去离子水)，每个处理设置3个重复。培养条件为光周期25℃，12h；暗周期15℃，12h。每隔一天从发芽盒中随机取5粒种子测其胚根、胚芽长度及鲜重，共测6次。0.01mM处理液可以加速黄瓜实生苗生长，胚根长度增加20％、胚芽长度增加16％、鲜重增加23％；0.5mM处理液显著降低黄瓜实生苗生长，胚根长度降低94％、胚芽长度降低75％、鲜重降低75％。

Claims (2)

1.4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮，其特征在于分子式为C13H16O5，结构式为：熔点420-422K，溶于水、乙醇、丙酮及氯仿，为外消旋体。
2.权利要求1所述的4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的合成方法，其特征在于步骤如下：
(1)将0.37g4,8-二苯甲酰酯基-1-四氢萘酮溶于12-15ml甲醇，加0.4-0.6g碳酸铯搅拌均匀，室温反应2h，除去甲醇，每次20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用45-60ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:8的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干燥，得到淡黄色粒状晶体：4-苯甲酰基-8-羟基-1-四氢萘酮，其分子式为C17H14O4；
(2)将上述C17H14O4溶于10ml无水四氢呋喃，加入1.2当量的氢化钠，室温下反应30min，再加入3.5-5ml环氧溴丙烷，升温至50℃反应30-45min，氯化铵淬灭反应，减压浓缩至干，用体积比1：1的乙酸乙酯和水混合液25ml萃取，有机相用45-60ml饱和食盐水除盐，再加50g无水硫酸钠除水后，减压浓缩至干，得淡黄色粒状晶体：4-苯甲酰基-8-(2-环氧基丙氧基)-1-四氢萘酮，其分子式为C20H18O5；
(3)将上述C20H18O5溶于7.5-10ml甲醇，加入1当量的碳酸铯，室温下反应30min，除去甲醇，每次15-20ml乙酸乙酯萃取，共萃取三次，合并萃取液，用25-30ml饱和食盐水除盐，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用体积比1:5的乙酸乙酯：石油醚混合液洗脱，洗脱液减压浓缩至干，得到：4-羟基-8-(2-环氧丙氧基)-1-四氢萘酮，其分子式为C13H14O4；
(4)将上述C13H14O4溶于5-7ml水，在70℃反应24h，减压浓缩至干燥，以重量比1:1与300-400目硅胶混匀，过200-300目硅胶柱，用乙酸乙酯洗脱，洗脱液减压浓缩至干，得到4-羟基-8-(2，3-二羟基丙氧基)-1-四氢萘酮的淡黄色针状晶体。
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