CN114835693B - 一种呋喃基吡咯化合物及其制备方法和应用 - Google Patents
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- 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
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
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Abstract
本发明提供一种呋喃基吡咯化合物及其制备方法和应用，以氨基葡萄糖盐酸盐与乙酰丙酮为原料加热回流得到2‑甲基‑3‑乙酰基‑5‑1′2′3′4′‑四羟基丁基吡咯，然后使其发生分子内成环反应，所得的化合物具有如下结构该化合物应用于卷烟加香，香味不易挥发，高温下能够裂解释放出多种小分子吡咯类挥发性香气成分，使烟气香质、量提高，提高卷烟抽吸品质。
Description
技术领域
本发明属于香烟添加剂技术领域，具体涉及一种呋喃基吡咯化合物及其制备方法及其在卷烟加香中的应用。
背景技术
近年来，随着人们健康意识的不断提升，卷烟消费者对卷烟的安全性关注日益增强，这对烟草行业的发展无疑是一个严峻的考验，低焦油卷烟产品的研发、生产与销售已是我国烟草行业发展的大势所趋。我国卷烟产品95％以上为烤烟型卷烟，其糖碱比较高，所以烟气酸性较为明显，游离烟碱所占比例较少，烟气生理强度较低，烟气较柔和，所以劲头比相同焦油含量的混合型卷烟小，其降焦难度更大。由上可知，对低焦油烤烟型卷烟的香味补偿研究更为迫切，因此被称为核心技术的香精香料技术广泛受到行业的高度重视。近年来，国内的烟用香精香料技术研究虽然有一定的进展，但主要还是以仿制为主，缺乏拥有自主知识产权的产品，与国际先进水平相比，还有较大差距，主要表现在基础性研究比较薄弱，缺乏对香料的系统性研究，不具备稳固的核心竞争力。
吡咯类化合物一直以其突出的香气特征和极低的阈值而被广泛关注和应用。它是一种重要的五元含氮杂环化合物，许多天然或非天然的吡咯衍生物都具有较为显著的生物学活性，被广泛应用于医药、食品、香料、日用化妆品、农药等其他领域。目前在食品挥发性成分中已经发现的吡咯衍生物有50多种，主要包括吡咯和它的烷基、酰基取代物、加氢产物和吲哚类化合物,他们大都具有焦香，坚果香、壤善香韵特性。此香类物质可很好地应用于卷烟调香研究，对卷烟加香应用具有很重要的意义。
虽然吡咯类香料香气特征突出，但是由于其阈值低(用量一般在百万分之一)，挥发性强，香味容易散失等缺点，使得吡咯香料化合物在食品加香中的应用受到相应的限制，人们一直试图寻找新型的吡咯类潜香化合物，在高温下能裂解释放小分子吡咯类挥发性香气成分，来代替挥发性的吡咯香料。
关于吡咯及其衍生物其合成方法很多，比较传统同时也比较经典的吡咯合成途径，就是克诺尔(Knorr)合成法与Paal.Knorr合成法，此外还有Hantzsch(汉栖)合成法。就合成途径来看大致可分为缩合法、环转换法、缩环法、和扩环法几类，其中缩合法研究的最为广泛和深入。随着人们对吡咯认识的不断加深，亟需开发更多增香效果更好的吡咯衍生物种类。
发明内容
本发明的目的在于针对现有技术的不足之处，提供一种新型的呋喃基吡咯化合物及其制备方法和应用，能够作为潜香化合物应用于卷烟中，并且具有较好的加香效果。
为解决上述技术问题，本发明采用如下技术方案：
一种呋喃基吡咯化合物，具有如下结构：
本发明的另一目的是提供上述呋喃基吡咯化合物的制备方法，包括如下步骤：
(1)碱性条件下，以氨基葡萄糖盐酸盐与乙酰丙酮为原料，在水溶液中加热回流，TLC跟踪检测，待原料点消失时终止反应，冷却结晶，析出的固体用丙酮重结晶得中间产物A；
(2)将中间产物A溶于无水甲醇中，加入冰醋酸，进行搅拌回流反应，TLC跟踪检测，待原料点消失时终止反应，往反应体系中加入无水碳酸钠，搅拌除去过量酸，抽滤后减压蒸馏，用丙酮重结晶得到最终产物。
优选地，步骤(1)所述碱性条件所述采用的调节剂为碳酸氢钠，所述氨基葡萄糖盐酸盐、乙酰丙酮与碳酸氢钠之间的摩尔比为：1：(1～1.3)：(1.3～1.6)。
优选地，步骤(2)中所述中间产物A与高无水甲醇、冰醋酸的比例为(0.2～0.3)mmol：1ml：(0.05～0.15)ml。
本发明的另一目的是提供上述的呋喃基吡咯化合物或者上述制备方法所得化合物在卷烟加香领域的应用，用作烟丝增香添加剂时，用量为烟丝质量的0.01％～0.03％。
与现有技术相比，本发明的有益效果为：
本申请得到的呋喃基吡咯化合物应用于卷烟加香，香味不易挥发，高温下能够裂解释放出多种小分子吡咯类挥发性香气成分，使烟气香质、量提高，提高卷烟抽吸品质。
附图说明
附图1是本发明的合成路线图；
附图2是本发明实施例1所得化合物的TG-DTG-DSC热重分析图。
具体实施方式
下面结合实施例对本发明作进一步说明。
实施例1
(1)中间产物A的合成
将D(+)-氨基葡萄糖盐酸盐(431.21mg,2mmol)溶于15mL水中，加入乙酰丙酮(240mg,2.4mmol)和NaHCO3(252mg,3mmol)。回流8h左右，TLC跟踪监测，待原料点消失时终止反应。低温静置约24h后，析出白色，抽滤，滤液用丙酮重结晶得到白色固体2-甲基-3-乙酰基-5-1′2′3′4′-四羟基丁基吡咯(中间产物A)0.418g，收率86％；
中间产物A的1H NMR(D2O,400.1MHz):δ:6.45(s,1H,CH),4.70(s,1H,CH),3.65(m,2H,H-1′,H-4′a),3.58(d,J＝2.9Hz,1H,CH),3.47-3.57(dd,J＝6.5Hz,1H,CH),2.36(s,3H,CH3),2.32(s,3H,CH3)；13CNMR(100.6MHz,D2O):δ:199.9(C＝O),137.9(C),130.5(C),119.8(C),108.0(CH＝C),73.8(CH),71.2(CH),66.3(CH),62.4(CH2),27.5(CH3),13.1(CH3)；HRMS:Calcd for[M+H]+.244.1185,Found:[M+H]+244.1188。
(2)呋喃基吡咯化合物的合成
将中间产物A(365mg，1.5mmol)溶于5mL无水甲醇中，加入0.5mL冰醋酸，搅拌下加热回流保持约8h，TLC跟踪监测，原料完全消失时，停止反应。然后再往反应体系中加入少量无水碳酸钠，继续搅拌约30分钟，以除去过量的酸，抽滤后减压蒸馏，用丙酮重结晶得到白色固体产物，274mg，收率81.2％。
化合物mp:164.4-166.7℃；IR(KBr):3326,2922,1624,1590,1463,1050cm-1；1HNMR 2.28(s,3H,CH3),2.32(s,3H,CH3)；3.74-3.77(t,J1＝1.72MHz,J2＝8.6MHz,H,CH)；4.13-4.18(m,J＝4.32MHz,J＝6.04MHz,2H,CH2)；4.18-4.20(d,J＝4.68MHz,1H,CH)；4.26-4.29(m,J＝1.76MHz,1H,CH),4.57-4.59(d,J＝8.44MHz,1H,CH)；6.54(s,1H,CH)；13C NMR(100MHz,CDCL3),δ:13.1(CH3),27.5(CH3),70.8(CH2),72.5(CH),75.2(CH)；75.5(CH),109.9(CH),120.0(C),127.5(C),138.9(C),199.6(C＝O)；HRMS calcd For[M+H]+226.1040,found[M+H]+226.1037。
将所得化合物进行TG-DTG-DSC热重分析，结果如图2所示。从TG-DTG曲线可看出，从30℃-249.9℃之间有较为缓慢的失重，失重台阶开始特征点在195.3℃，此时化合物开始降解，到224.9℃时失重速度最快，此阶段失重率19.03％。249.9℃-900℃之间化合物失重率达到45.6％，900℃以后TG和DTG曲线基本趋于平稳，此阶段化合物基本分解完全。
DSC曲线表示化合物的熔化过程：在124.9℃开始熔化,在159.2℃开始出现吸热主峰,随后在226.3℃出现放热峰,这与224.9℃时失重速度最快基本吻合。在560.5℃出现放热峰，可能是由于未分解的物质发生相变、吸附或吸收。
加香试验
将化合物1按照不同的量均匀添加到单料烟丝中，卷制成烟支，由评吸专家综合评定打分，评吸结果如下表1所示：
表1卷烟加香结果
其中：
对照1样品为实施例1所得中间产物A。
对照2样品为采用CN1049616691A中记载的方法，制备得到的N-异丙基-2-甲基-5-甲酰基-3-吡咯甲酸乙酯。
本发明的保护范围不限于上述的实施例，显然，本领域的技术人员可以对本发明进行各种改动和变形而不脱离本发明的范围和精神。倘若这些改动和变形属于本发明权利要求及其等同技术的范围，则本发明的意图也包含这些改动和变形在内。
Claims (2)
1.一种呋喃基吡咯化合物在卷烟加香领域中的应用，其特征在于，用作烟丝增香添加剂，所述呋喃基吡咯化合物的结构为：
。
2.如权利要求1所述的应用，其特征在于，用作烟丝增香添加剂时，所述化合物的用量为烟丝质量的0.01%~0.03%。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110149374X | 2021-02-02 | ||
| CN202110149374 | 2021-02-02 |
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| CN104961669A (zh) * | 2015-03-18 | 2015-10-07 | 河南农业大学 | N-烃基-2-甲基-5-甲酰基-3-吡咯甲酸酯的制备方法及其在卷烟加香中的应用 |
| CN105777678A (zh) * | 2016-03-30 | 2016-07-20 | 云南中烟工业有限责任公司 | 一种2-甲酯基呋喃类增香剂化合物、其制备方法及其在卷烟保润中的应用 |
| CN114467047A (zh) * | 2019-10-08 | 2022-05-10 | 华为技术有限公司 | 光学装置、成像装置及移动设备 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104961669A (zh) * | 2015-03-18 | 2015-10-07 | 河南农业大学 | N-烃基-2-甲基-5-甲酰基-3-吡咯甲酸酯的制备方法及其在卷烟加香中的应用 |
| CN105777678A (zh) * | 2016-03-30 | 2016-07-20 | 云南中烟工业有限责任公司 | 一种2-甲酯基呋喃类增香剂化合物、其制备方法及其在卷烟保润中的应用 |
| CN114467047A (zh) * | 2019-10-08 | 2022-05-10 | 华为技术有限公司 | 光学装置、成像装置及移动设备 |
Non-Patent Citations (3)
| Title |
|---|
| Boyu Li et al..InCl3-catalyzed synthesis of C-pyrrolyl glycosides via tandem condensation of aminosugars and 1,3-dicarbonyl compounds in water.《Tetrahedron Letters 》.2011,第52卷(第30期),第 3891-3894页. * |
| 严琳 等.核苷类似物的设计合成及其抗肿瘤活性.《河南大学学报（自然科学版）》.2011,第41卷(第3期),第257-261页. * |
| 项燕飞 等.CoCl2•6H2O、AlCl3•6H2O水相催化合成C-吡咯糖苷.《化学研究与应用》.2013,第25卷(第10期),第1426-1429页. * |
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