CN114920640A - 一种氯代环戊酮衍生物及其合成方法 - Google Patents

一种氯代环戊酮衍生物及其合成方法 Download PDF

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CN114920640A
CN114920640A CN202210677680.5A CN202210677680A CN114920640A CN 114920640 A CN114920640 A CN 114920640A CN 202210677680 A CN202210677680 A CN 202210677680A CN 114920640 A CN114920640 A CN 114920640A
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朱钢国
勒思雅
邱佳燕
罗芳
孔黎春
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Zhejiang Normal University CJNU
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Abstract

本发明公开了一种氯代环戊酮衍生物Ⅰ及其制备方法，将式Ⅱ结构的3‑甲基丁醛、式Ⅲ结构的对甲基苯乙炔氯，十钨酸四丁基铵TBADT加入到溶剂中，反应后得到。通过光催化实现了[3+2]环加成反应，以100％的原子经济性合成了氯代环戊酮衍生物。本发明还提供了该氯代环戊酮衍生物的合成应用，通过加入碳酸钾来进行消除反应制备环戊烯酮衍生物Ⅳ，实现了芳香倍半萜laurokamurene B及Cuparene的高效合成。

Description

一种氯代环戊酮衍生物及其合成方法
技术领域
本发明属于有机合成领域，具体涉及一种氯代环戊酮衍生物及其合成方法。
背景技术
倍半萜类化合物作为天然产物的一个组成部分广泛存在于广泛分布于植物、昆虫、海洋生物和微生物等动植物体。而具有芳环结构的花侧柏烷型及月桂烯型倍半萜这两类天然产物的合成一直是化学家们关注的热点。其中，具有重要的生物功能及生理活性的天然产物芳香倍半萜laurokamurene B及Cuparene的合成也受到了广泛关注。
2007年，Srikrishna等人首次报道了以异丁酸为起始原料合成了(±)-laurokamurene B，反应利用艾兰德变体的克莱森重排反应和闭环置换反应(RCM)的结合来作为关键反应。该反应经经10步反应来实现(±)-laurokamurene B的全合成，通过环戊烯酮化合物脱羰反应(±)-laurokamurene B，最终合成总收率约为22％。
2019年，以1,3-环戊二酮为起始原料，经过5个步骤(总收率为45.4％)合成了((±)-laurokamurene B，反应利用β烷氧基烯酮和芳基金属化合物(格氏试剂或有机锂)参与的Stork–Danheiser反应和甲基化策略来构建芳香倍半萜，总收率为45.4％，反应过程如下所示：
Figure BDA0003695395400000011
(±)-Cuparene作为另外一种常见的芳香倍半萜，其合成方法也吸引了大量的学者研究。Srikrishna等人报道了从β-紫罗兰酮出发，经过7步反应，合成芳香倍半萜(±)-Cuparene。由于环戊烷酮类化合物(±)-β-cuparenone可以顺利的通过基斯内尔-沃尔夫-黄鸣龙还原反应是将酮羰基还原为亚甲基来实现(±)-Cuparene的合成，大批的学者研究方向侧重在了(±)-β-cuparenone的合成上，反应过程如下所示：
Figure BDA0003695395400000021
而(±)-β-cuparenone的合成通常会底物预官能团化，操作繁琐，多步来实现，所得总产率往往较低。2007年，Ray等人采用预官能团化的溴代烯醛与溴代烯烃通过金属钯催化串联Heck环化反应来实现环戊烯酮的合成，该环戊烯酮通过脱羰形成(±)-β-cuparenone，随后通过还原得到(±)-Cuparene，反应过程如下所示：
Figure BDA0003695395400000022
通过文献报道，由环戊烯酮类化合物合成芳香倍半萜laurokamurene B及Cuparene是可行的，开发更新型的、更高效、更温和的策略构建环戊烯酮骨架具有重要研究意义。烯烃是可以通过卤代烃的消除反应来合成，同时近年来自由基反应由于温和高效的特点受到广泛关注，因此，设计合理的自由基催化反应体系，实现卤代环戊酮的合成进而实现环戊烯酮类化合物的合成，从而进一步实现芳香倍半萜laurokamurene B及Cuparene的合成，这些在理论研究和实际应用中都具有重要意义。
发明内容
本发明提供了一种氯代环戊酮衍生物及其合成方法，采用3-甲基丁醛作为新的三碳合成子，在光催化剂十钨酸四丁基铵的催化下催化[3+2]环加成反应。该催化循环经历醛的脱氢反应，自由基加成反应，1,5-氢原子转移，反baldwin 5-endo-trig环化及抽氢反应得以实现。反应条件温和，原料易得。此外，本发明同时提供了该氯代环戊酮衍生物的合成应用，通过消除反应，成功合成了环戊烯酮衍生物。并将该衍生物成功应用到芳香倍半萜laurokamurene B及Cuparene得合成中。由该环戊烯酮衍生物出发，仅需两步就能高效的合成芳香倍半萜laurokamurene B及Cuparene。
一种氯代环戊酮衍生物，为式Ⅰ结构：
Figure BDA0003695395400000031
一种氯代环戊酮衍生物的制备方法，包括以下步骤：
将式Ⅱ结构的3-甲基丁醛、式Ⅲ结构的对甲基苯乙炔氯，十钨酸四丁基铵TBADT加入到溶剂中，在反应环境中，形成反应体系，反应完成后经后处理得到式Ⅰ结构的氯代环戊酮衍生物；
Figure BDA0003695395400000032
涉及反应的具体合成路线如下所示：
Figure BDA0003695395400000033
该制备方法在光催化剂十钨酸四丁基铵的催化下催化[3+2]环加成反应。该催化循环经历醛的脱氢反应，自由基加成反应，1,5-氢原子转移，反baldwin5-endo-trig环化及抽氢反应得以实现。
所述的反应环境为氮气氛围，所述的反应环境为：35～45W，370～410nm的光催化灯照射，进一步优选，室温25℃下40W,390nm的光催化灯照射。
所述的反应的条件为：15～35℃反应10～25小时，进一步优选，25℃反应15小时。所述的反应体系的反应时间为15h。
所述的式Ⅱ结构的3-甲基丁醛、式Ⅲ结构的对甲基苯乙炔氯、十钨酸四丁基铵TBADT的摩尔比为1～3：0.5～1.5：0.01～0.04，进一步优选为2：1：0.02。
所述的溶剂为乙腈与水(体积比为10:1)组成的混合溶剂。
所述的后处理包括：淬灭、抽滤、萃取、洗涤有机相、干燥和柱层析分离。
所述的淬灭采用加水淬灭，所述的萃取采用乙酸乙酯萃取，所述的洗涤有机相采用饱和食盐水洗涤，所述的干燥采用无水硫酸钠干燥，所述的柱层析分离采用硅胶柱层析分离。
一种氯代环戊酮衍生物的合成应用，其可以通过加入碳酸钾来进行消除反应制备环戊烯酮衍生物Ⅳ，该环戊烯酮衍生物Ⅳ只需两步，经过选择性甲基化、还原反应等，可以顺利高效的实现芳香倍半萜(±)-Laurokamurene B及(±)-Cuparene的合成，涉及反应的具体合成路线如下所示：
Figure BDA0003695395400000041
同现有技术相比，本发明具有如下优点：
一、3-甲基丁醛作为新的三碳合成子，通过光催化实现了[3+2]环加成反应，以100％的原子经济性合成了氯代环戊酮衍生物。
二、首次通过由氯代环戊酮作为来合成芳香倍半萜laurokamurene B及Cuparene，与传统的合成方法相比，步骤大幅缩短，原料简单易得。
具体实施方式
氯代环戊酮衍生物I的制备
氮气氛围下，将3-甲基丁醛(34.4mg,0.4mmol)和对甲基苯乙炔氯(30.1mg,0.2mmol)加入到含有十钨酸四丁基铵TBADT(10.6mg,0.004mmol)的2毫升乙腈水(体积比MeCN:H2O＝10:1)溶液中，混合形成反应体系，该体系在光催化灯(Kessil PR160,40W,390nm)的照射下室温反应15小时后，向反应体系中加入水淬灭反应，用乙酸乙酯萃取反应三次，合并有机相，用饱和氯化钠溶液洗涤并用无水硫酸钠干燥，旋干溶剂，柱层析(PE:EA＝40:1，硅胶柱层析分离)分离得到41.2mg白色固体氯代环戊酮衍生物I。mp127-128℃,dr>20:1；Flash column chromatography conditions:petroleum ethers/EtOAc＝50:1；产物数据表征：1H NMR(400MHz,CDCl3)δ7.21(d,J＝7.9Hz,2H),7.11(d,J＝8.0Hz,2H),4.69(d,J＝12.8Hz,1H),3.19(d,J＝12.8Hz,1H),2.52(d,J＝19.0Hz,1H),2.43(d,J＝18.9Hz,1H),2.37(s,3H),1.17(s,3H),0.86(s,3H)；13C NMR(151MHz,CDCl3)δ209.3,137.4,131.5,129.2,128.4,61.8,61.2,52.0,37.6,28.3,23.2,21.1；HRMS(ESI)m/z:[M+H]+Calcd forC14H17ClO+H+:237.1041；Found 237.1032。
反应式如下：
Figure BDA0003695395400000051
环戊烯酮衍生物Ⅳ的制备
将氯代环戊酮衍生物I(47.2mg,0.2mmol)加入到含N,N-二甲基甲酰胺DMF(2mL)的反应管中，随后加入碳酸钾K2CO3(55.2mg,0.4mmol)形成反应体系，体系在80℃下反应4小时，向反应体系中加入水淬灭反应，用乙酸乙酯萃取反应三次，合并有机相，用饱和氯化钠溶液洗涤并用无水硫酸镁干燥，旋干溶剂，柱层析(PE:EA＝20:1，硅胶柱层析分离)分离得到37mg无色液体环戊烯酮衍生物Ⅳ,产率93％。产物数据表征：1H NMR(400MHz,CDCl3)δ7.43-7.40(m,2H),7.23(d,J＝8.0Hz,2H),6.18(s,1H),2.49(s,2H),2.40(s,3H),1.43(s,6H)；13C NMR(101MHz,CDCl3)δ207.5,183.5,140.0,131.7,129.2,128.7,127.8,53.7,43.6,28.1,21.3.
反应式如下：
Figure BDA0003695395400000061
芳香倍半萜laurokamurene B的制备
干燥的反应管中加入环戊烯酮衍生物Ⅳ(40.0mg,0.2mmol)及1mL四氢呋喃中，并将其放置于-78℃环境中，加入双(三甲基硅基)胺基锂LiHMDS(0.24mL,1.0M solution inTHF)形成反应体系反应1小时，加入碘甲烷(42.6mg,0.3mmol)，随后反应升至室温并于室温下反应2小时。加入饱和氯化铵溶液淬灭，用乙酸乙酯萃取反应，并用无水硫酸镁干燥，旋干溶剂，柱层析(PE:EA＝50:1，硅胶柱层析分离)分离得到36mg无色液体环戊烯酮衍生物Ⅴ，产率84％。产物数据表征：1H NMR(600MHz,CDCl3)δ7.39(d,J＝8.2Hz,2H),7.23(d,J＝7.9Hz,2H),6.16(s,1H),2.40(s,3H),2.37(q,J＝7.32Hz,1H),1.35(s,3H),1.23(s,3H),1.15(d,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3)δ209.7,182.4,139.7,132.1,129.2,127.8,127.8,54.6,46.7,26.4,24.7,21.3,9.8.
将氯代环戊酮衍生物Ⅴ用Srikrishna等人的合成方法(A.Srikrishna,I.A.Khan,R.R.Babu,A.Sajjanshetty,Tetrahedron2007,63,12616)可以合成出芳香倍半萜laurokamurene B.
反应式如下：
Figure BDA0003695395400000062
芳香倍半萜Cuparene的制备
在干燥的反应管中加入环戊烯酮衍生物Ⅳ(40.0mg,0.2mmol)和乙酰丙酮镍Ni(acac)2(5.1mg,0.02mmol)，将反应管放入0℃环境中，该反应体系加入四氢呋喃THF(2mL)和三甲基铝Me3Al(0.2mL,1.0M solution in THF)，室温下反应两小时后，向反应体系中加入饱和氯化铵溶液淬灭反应，用乙酸乙酯萃取反应三次，合并有机相，用饱和氯化钠溶液洗涤并用无水硫酸钠干燥，旋干溶剂，柱层析(PE:EA＝50:1，硅胶柱层析分离)分离得到36mg无色液体氯代环戊酮衍生物Ⅵ。产物数据表征：1H NMR(600MHz,CDCl3)δ7.24-7.21(m,2H),7.16(d,J＝8.0Hz,2H),3.15(d,J＝18.3Hz,1H),2.36(t,J＝9.5Hz,5H),2.26(dd,J＝19.5,1.2Hz,1H),1.44(s,3H),1.25(s,3H),0.75(s,3H)；13C NMR(151MHz,CDCl3)δ218.3,141.2,135.8,128.7,126.5,52.4,50.7,47.8,41.8,26.2,24.4,24.1,20.8.
将氯代环戊酮衍生物Ⅵ用Nanda等人的合成方法(R.Kumar,J.Halder,S.Nanda,Tetrahedron 2017,73,809)可以合成出芳香倍半萜Cuparene.
反应式如下：
Figure BDA0003695395400000071

Claims (8)

1.一种氯代环戊酮衍生物，其特征在于，为式Ⅰ结构：
Figure RE-FDA0003756024790000011
2.根据权利要求1所述的氯代环戊酮衍生物的合成方法，其特征在于，包括以下步骤：
将式Ⅱ结构的3-甲基丁醛、式Ⅲ结构的对甲基苯乙炔氯、十钨酸四丁基铵TBADT加入到溶剂中，在反应环境中，形成反应体系，反应完成后经后处理得到式Ⅰ结构的氯代环戊酮衍生物；
Figure RE-FDA0003756024790000012
3.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的反应环境为氮气氛围。
4.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的反应环境为：35～45W，370～410nm的光催化灯照射。
5.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的反应的条件为：15～35℃反应10～25小时。
6.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的式Ⅱ结构的3-甲基丁醛、式Ⅲ结构的对甲基苯乙炔氯、十钨酸四丁基铵TBADT的摩尔比为1～3：0.5～1.5：0.01～0.04。
7.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的溶剂为乙腈与水组成的混合溶剂。
8.根据权利要求2所述的氯代环戊酮衍生物的合成方法，其特征在于，所述的后处理包括：淬灭、抽滤、萃取、洗涤有机相、干燥和柱层析分离。
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