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大麻素的合成：“水相”和“水表面”方法：十二烷基硫酸钠胶束的影响

Synthesis of Cannabinoids: "In Water" and "On Water" Approaches: Influence of SDS Micelles.

作者信息

Quílez Del Moral José F, Ruiz Martínez Cristina, Pérez Del Pulgar Helena, Martín González Juan Eduardo, Fernández Ignacio, López-Pérez José Luis, Fernández-Arteaga Alejandro, Barrero Alejandro F

机构信息

Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain.

Department of Chemistry and Physics, Research Centre CIAIMBITAL, University of Almería, 04120 Almería, Spain.

出版信息

J Org Chem. 2021 Feb 19;86(4):3344-3355. doi: 10.1021/acs.joc.0c02698. Epub 2021 Feb 3.

DOI:10.1021/acs.joc.0c02698
PMID:33533618
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9087200/
Abstract

We have proven that the biomimetic-like synthesis of cannabinoids from citral and the corresponding phenolic counterpart may well be carried out using water as a solvent. The influence of different additives such as surfactants was also analyzed. Rationalization of the reaction mode and regiochemistry of the processes were provided in terms of "on water" and "in water" reactions. The same reactions were conducted in organic media using Ga(III) salts as catalysts. Worthy of being underlined, an unprecedented formal [2+2+2] process was found to occur between two citral molecules and the corresponding phenolic species in both aqueous and organic environments. Computational studies were performed in order to gain a comprehensive mechanistic and energetic understanding of the different steps of this singular process. Finally, the influence of SDS micelles in the chemical behavior of olivetol and citral was also pursued using PGSE diffusion and NOESY NMR studies. These data permitted to tentatively propose the existence of a mixed micelle between olivetol and SDS assemblies.

摘要

我们已经证明，使用水作为溶剂可以很好地实现从柠檬醛和相应的酚类化合物仿生合成大麻素。还分析了不同添加剂（如表面活性剂）的影响。根据“水相上”和“水相中”反应对反应模式和过程的区域化学进行了合理化解释。使用Ga(III)盐作为催化剂在有机介质中进行了相同的反应。值得强调的是，发现在水性和有机环境中，两个柠檬醛分子与相应的酚类物质之间会发生前所未有的形式上的[2+2+2]反应。进行了计算研究，以便全面了解这一独特过程不同步骤的机理和能量情况。最后，还使用PGSE扩散和NOESY NMR研究了SDS胶束对橄榄醇和柠檬醛化学行为的影响。这些数据初步表明橄榄醇和SDS组装体之间存在混合胶束。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/9d182fbd8716/jo0c02698_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/b074d6c03d5e/jo0c02698_0005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/cbdfbd866425/jo0c02698_0007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/33501a6ff0d5/jo0c02698_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/118622c8b442/jo0c02698_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/fd603dea61e5/jo0c02698_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/ab34d5b2e02f/jo0c02698_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/9d182fbd8716/jo0c02698_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/b074d6c03d5e/jo0c02698_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/cbbe075e5367/jo0c02698_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/7a0080a12fae/jo0c02698_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/cbdfbd866425/jo0c02698_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/e332457ce7a7/jo0c02698_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/33501a6ff0d5/jo0c02698_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/118622c8b442/jo0c02698_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/fd603dea61e5/jo0c02698_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5726/9087200/9d182fbd8716/jo0c02698_0010.jpg

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