CN113620900A - 一种鉴别试剂的制备方法及其应用 - Google Patents
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- 238000002360 preparation method Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 241000219198 Brassica Species 0.000 claims description 25
- 235000003351 Brassica cretica Nutrition 0.000 claims description 25
- 235000003343 Brassica rupestris Nutrition 0.000 claims description 25
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 25
- 235000010460 mustard Nutrition 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000001514 detection method Methods 0.000 claims description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000003556 assay Methods 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 abstract description 5
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 22
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000015067 sauces Nutrition 0.000 description 6
- 244000195452 Wasabia japonica Species 0.000 description 5
- 235000000760 Wasabia japonica Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000011194 food seasoning agent Nutrition 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000003291 Armoracia rusticana Species 0.000 description 2
- 235000011330 Armoracia rusticana Nutrition 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
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- 230000000638 stimulation Effects 0.000 description 2
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 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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Abstract
本发明为一种鉴别试剂的制备方法及其应用,涉及5,6‑二甲基四氢‑1,3‑恶嗪‑2‑硫酮合成方法及其的应用。本发明公开了一种5,6‑二甲基四氢‑1,3‑恶嗪‑2‑硫酮,及其合成方法,该合成方法路线短,无其他杂质,反应产率高,目标产物纯度高。另外,本发明提供了合成化合物的新用途。
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种鉴别试剂合成方法和及其应用。
背景技术
结构式1所示的化合物是5,6-二甲基四氢-1,3-恶嗪-2-硫酮,5,6-Dimethyltetrahydro-1,3-oxazine-2-thione有机化合物,该化合物可作为鉴定试剂,与乙醇发生反应,生成5,6-二甲基四氢-1,3-恶嗪-2-硫酮,用于鉴别芥末或芥末酱是否含有异硫氰酸烯丙酯的分析。
芥末微苦,辛辣芳香,对口舌有强烈刺激,味道十分独特,芥末粉润湿后有香气喷出,具有催泪性的强烈刺激性辣味,对味觉、嗅觉均有刺激作用。可用作泡菜、腌渍生肉或拌沙拉时的调味品。芥末酱由芥末粉或山葵,辣根或其他粉类经发制、调配而成的一种常见调味品,具有强烈的刺激性气味和清爽的味觉感受,可以作为夏季凉拌菜的调料。
异硫氰酸烯丙酯(Allyl isothiocyanate)性状为无色至淡黄色透明油状液体,有强烈的刺激性气味,遇光易变色分解。微溶于水,能溶于醇、醚和二硫化碳。异硫氰酸烯丙酯是食品香料,其它还用于有机合成中间体的原料、重氨感光纸的助剂、杀虫剂等方面。还可用于辣酱油类、肉类(肉食加工品)、醋腌食品以及其它调味品。
异硫氰酸烯丙酯是芥末或wasabi的重要成分。可以用于鉴别芥末的质量。质量好的芥末,异硫氰酸烯丙酯含量高。如果是假的芥末和wasabi,其中的异硫氰酸烯丙酯微不足道。因此可以异硫氰酸烯丙酯和其他物质反应的原理用于鉴别芥末或wasabi的质量的优劣。
发明内容
针对现有5,6-二甲基四氢-1,3-恶嗪-2-硫酮合成路线长,成本高等问题。本发明提供了一种5,6-二甲基四氢-1,3-恶嗪-2-硫酮,及其合成方法,该合成方法路线短,无其他杂质,反应产率高,目标产物纯度高。另外,提供了合成化合物可以用作鉴别芥末或wasabi的新应用。
为解决上述问题,本发明采用如下的技术方案:
一种结构式1的合成方法
包括以下步骤:
I.结构式2的化合物,
与结构3的化合物反应,
得到结构式1的化合物:
优选的,所述步骤(I)中,结构式2的化合物与结构式3的化合物的反应摩尔比为0.5:1-1.5:1,更优选为0.8:1-1.2:1。
优选的,所述步骤(I)中,反应温度为10℃-50℃,优选为20℃-30℃。
优选的,所述步骤(I)中,反应溶剂为乙醇。
本发明所述结构式为1与2的化合物可以通过商品销售渠道直接购买。
本发明的另一目的是提供一种合成结构式1的化合物的用途,结构式1的化合物可作鉴别试剂用于鉴别芥末或wasabi的新应用。
结构式1的化合物作为鉴定试剂用于芥末酱检测步骤包括:
1.芥末用正丁烷提取,吸取提取液。
2.加入乙醇,震荡均匀,反应10分钟到30小时,
3.然后进行LC-MS检测。
本发明所述的结构式1化合物的合成方法,有益效果是:合成路线短,试剂廉价,操作步骤简单,产率高。可以用于
附图说明
图1.实施例1的化合物2的LC-MS图。
图2.实施例1的化合物2的质谱图。
图3.实施例1的合成化合物1的LC-MS图。
图4.实施例2的合成化合物1的质谱图。
具体实施方式
下面结合具体实施例,进一步阐述本发明。应理解,这些实施例仅用于说明本发明而不用于限制本发明的范围。此外应理解,在阅读了本发明讲授的内容之后,本领域技术人员可以对本发明作各种改动或修改,这些等价形式同样落于本申请所附权利要求书所限定的范围。
实施例1
在单口瓶中投入乙醇(99%)10mL,异硫氰酸烯丙酯(结构式2化合物)10ml,20℃-35℃下搅拌过夜。收集目标产物。得到结构式1的化合物。
通过GC-MS分析产物结构。分子量计算值为145,质谱检测值M/Z:145,质谱检测结果与理论值相符。
实施例2
在单口瓶中投入乙醇(95%)30mL,异硫氰酸烯丙酯(结构式2化合物)30ml,30℃下搅拌40小时,收集目标产物。得到结构式1的化合物。通过GC-MS分析产物结构。分子量计算值为145,质谱检测值M/Z:145,质谱检测结果与理论值相符。
实施例3
在单口瓶中投入乙醇(95%)30mL,异硫氰酸烯丙酯(结构式2化合物)30ml,25℃下搅拌10小时,收集目标产物。得到结构式1的化合物。通过GC-MS分析产物结构。分子量计算值为145,质谱检测值M/Z:145,质谱检测结果与理论值相符。
实施例4
合成结构1的化合物,作为芥末酱鉴定试剂。芥末酱用n-hexane提取,然后加入乙醇反应进行30分钟,进行GC-MS常规检测。程序升温,50℃-250℃,50分钟。
检测结果表明,当加入鉴定试剂,进行鉴定反应后,所检测的结构式1。表明合成结构式1的化合物,作为芥末酱鉴定试剂。
实施例5
合成结构1的化合物,作为芥末酱鉴定试剂。芥末酱用n-hexane提取,然后加入乙醇反应进行60分钟,进行GC-MS常规检测。程序升温,50℃-250℃,50分钟。
检测结果表明,当加入鉴定试剂,进行鉴定反应后,所检测的结构式1。表明合成结构式1的化合物,作为芥末酱鉴定试剂。
实施例6
合成结构1的化合物,作为芥末酱鉴定试剂。芥末酱用n-hexane提取,然后加入乙醇反应进行90分钟,进行GC-MS常规检测。程序升温,50℃-250℃,50分钟。
检测结果表明,当加入鉴定试剂,进行鉴定反应后,所检测的结构式1。表明合成结构式1的化合物,作为芥末酱鉴定试剂。
Claims (9)
3.根据权利要求1所述的化合物,其特征在于,结构式2的化合物与结构式3的化合物的反应摩尔比为0.5:1-1.5:1。
4.根据权利要求1所述的化合物,其特征在于,结构式2的化合物与结构式3的化合物的反应温度为10℃-50℃。
5.一种权利要求1所述的结构式(1)所示的化合物作为作鉴别芥末的应用。
6.结构式1的化合物作为鉴定试剂用于芥末酱检测步骤包括:提取;和LC-MS检测。
7.根据权利要求6所述的化合物,其特征在于,所述提取溶剂包括正丁烷,丁烷,戊烷。
8.根据权利要求6所述的化合物,其特征在于,所述提取完成后加入乙醇进行反应。
9.根据权利要求8所述的化合物,其特征在于,所述反应时间为10分钟到30小时。
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Citations (2)
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CN105669586A (zh) * | 2016-03-03 | 2016-06-15 | 中国科学院化学研究所 | 一种制备3,4-二氢苯并[b][1,4]恶嗪衍生物的方法 |
CN108794489A (zh) * | 2018-07-18 | 2018-11-13 | 香港浸会大学深圳研究院 | 一种衍生化试剂及其制备方法与应用 |
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CN105669586A (zh) * | 2016-03-03 | 2016-06-15 | 中国科学院化学研究所 | 一种制备3,4-二氢苯并[b][1,4]恶嗪衍生物的方法 |
CN108794489A (zh) * | 2018-07-18 | 2018-11-13 | 香港浸会大学深圳研究院 | 一种衍生化试剂及其制备方法与应用 |
Non-Patent Citations (2)
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A. S. FISYUK: "Interaction of methyl N-(3-oxoalkyl)carbamates, S-methyl -carbamates, and -dithiocarbamates with sodium borohydride. Synthesis of tetrahydro-1,3-oxazin-2-ones and -thiones", 《CHEMISTRY OF HETEROCYCLIC COMPOUNDS》, vol. 37, no. 5, pages 597 - 609, XP002526363, DOI: 10.1023/A:1011660706513 * |
F. A. HASHEM ET AL.: "Isothiocyanates in myrosinase-treated herb extract of Cleome chrysantha Decne. and their antimicrobial activities", 《PHYTOTHERAPY RESEARCH》, vol. 14, no. 4, pages 284 - 287 * |
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