CAS: 500-49-2; Divarin

上下游产品

1,3-dimethoxy-5-propylbenzene 2-hydroxy-4-methoxy-6-propylbenzoic acid divaricatic acid 2,4-dihydroxy-6-propylbenzoic acid 2,4-dihydroxy-6-propylbenzaldehyde 8-tetrahydr°Cannabinol3-norpentyl-3-propyl-8-tetrahydr°Cannabinol tetrahydr°Cannabivarin CBGV

3,5-二甲氧基苄醇置于萘,氢溴酸,Lithium,溶剂黄146,三乙胺,Sodium Iodide,锌体系中,用 四氢呋喃,乙二醇二甲醚 作为反应溶剂,化学反应 15.08H,反应生成 5-丙基-1,3-苯二酚
参考文献:5位间苯二酚的简单合成:有趣的生物活性分子的再访家族.
标题:5位间苯二酚的简单合成:有趣的生物活性分子的再访家族.
摘要:3,5-二甲氧基苄基三甲基甲硅烷基醚(3)与不同醛(n-Prcho,Nc(11)h(23)cho,Mecho,Phcho)在锂粉和催化量萘(4 Mol)的存在下反应%)在水解后得到中等产率的预期醇4.这些化合物通过相应的甲磺酸酯5脱羟基或直接由苄基衍生物通过催化加氢脱羟基,得到化合物6,最后将其脱甲基,得到5-烷基-3,5-二羟基间苯二酚,例如橄榄酚(7A),格列维洛(7B),1,3-二羟基-5-丙基苯(7C)或二氢吡sil硅(7D).醇衍生物4脱水后再去甲基化,会反应生成羟基化的1,2-苯乙烯型结构,如宾诺硅碱(9D),白藜芦醇(9E)或甲基吡啶(9F),在某些情况下,可以将其氢化得到饱和分子,例如康普他汀b-4四甲基醚(6F)或金联双苄基(6G).最后,当在其他亲电子试剂[me(3)sicl,T-Bucho,Ch(3)(ch(2))(4)cho,4-Me(3)的存在下进行化合物3的萘催化
DOI:10.1021/jo9610624

专利信息

专利号:WO-2025217205-A1
优先权日:2024-04-08
标 题:Synthesis of (-)-trans-δ9-tetrahydrocannabivarin (δ9-thcv) and analogs thereof
发明人：HAGHDOOST MEHDI; ROBERTS MATTHEW; THOMAS BRIAN; DICKINSON LUKE; NIKITIN EDWARD
权利人:NALU BIO INC
摘要:A method is provided for the synthesis of (-)-trans-Δ9-tetrahydrocannabivarin (Δ9-THCV) and analogs thereof such that in the reaction product, the molar ratio of the Δ9 isomer to incidentally formed Δ8 isomers is greater than 4:1. Synthesis is carried out by combining a selected cannabinoid reactant, e.g., cannabidivarin (CBDV) or an analog thereof, with an acid in a solvent for the cannabinoid reactant, wherein the acid comprises (i) a Lewis acid having an acid softness index value in the range of -10 ΔG0 f, M n+ to ‑150 ΔG0 f, M n+, (ii) a Brønsted acid having a pKa in the range of -4.0 to +4.0, or (iii) a combination of (i) and (ii), under reaction conditions comprising a reaction temperature in the range of ‑0 °C to 25 °C and a reaction time in the range of 1 hour to 24 hours. The reaction is thereafter quenched with base and the solvent removed, wherein the crude reaction product so provided may be purified, e.g., chromatographically purified. Also provided is a method for synthesizing Δ9-THCV that further includes synthesis of the cannabinoid reactant. The invention additionally provides novel cannabinoid compositions that may be synthesized using the aforementioned methodology.

专利号:US-2024116890-A1
优先权日:2022-09-28
标 题 :Large scale synthesis of cannabinol
发明人：COLLINS ARIANNA C; CRUCES IVAN; RAY KYLE; CRUCES WESTLEY
权利人:COLORADO CHROMATOGRAPY LLC
摘要:Methods for producing cannabinol, cannabivarin, or derivatives thereof are disclosed. The methods disclosed herein can be employed for large scale synthesis or semi-synthesis of the compounds, including multi-kilogram quantities of the compounds.

专利号:US-11046978-B2
优先权日:2016-03-16
标 题:Synthesis of isoprenoids and derivatives
发明人：GONZALEZ RAMON; CLOMBURG JAMES M; CHEONG SEOKJUNG
权利人:UNIV RICE WILLIAM M
摘要:This disclosure generally relates to the use of enzyme combinations or recombinant microbes comprising same to make isoprenoid precursors, isoprenoids and derivatives thereof including prenylated aromatic compounds. Novel metabolic pathways exploiting Claisen, aldol, and acyioin condensations are used instead of the natural mevalonate (MVA) pathway or 1-deoxy-d-xylulose 5-phosphate (DXP) pathways for generating isoprenoid precursors such as isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), and geranyl pyrophosphate (GPP). These pathways have the potential for better carbon and or energy efficiency than native pathways. Both decarboxylative and non-carboxylative condensations are utilized, enabling product synthesis from a number of different starting compounds. These condensation reactions serve as a platform for the synthesis of isoprenoid precursors when utilized in combination with a variety of metabolic pathways and enzymes for carbon rearrangement and the addition/removal of functional groups. Isoprenoid alcohols are key intermediary products for the production of isoprenoid precursors in these novel synthetic metabolic pathways.

专利号:WO-2024263718-A1
优先权日:2023-06-23
标 题:Synthesis of (-)-trans-δ9-tetrahydrocannabivarin and analogs thereof
发明人：ROGGEN MARKUS; SAMMIS GLENN M; ROBERTS MATTHEW
权利人:NALU BIO INC
摘要:A method is provided for the synthesis of (-)-trans-Δ9-tetrahydrocannabivarin (Δ9-THCV) and analogs thereof starting from a resorcinol reactant, such as divarinol, and a p-menthadienol reactant and proceeding through Δ8-THCV as intermediate. The initial step of the reaction between the resorcinol reactant and the p-menthadienol reactant is carried out in a solvent at elevated temperature in the presence of a Brønsted acid to form the Δ8 isomer. The Δ8 double bond is halogenated and the halogenated intermediate thus formed treated with a strong base to effect dehydrohalogenation and provide the desired product, Δ9-THCV, in high yield, with minimal or no remaining Δ8-THCV.

专利号:US-12264143-B2
优先权日:2020-12-17
标 题:Synthesis of cannabinoids and cannabinoid precursors, and related compounds, formulations, and methods of use
发明人：SAMMIS GLENN M; ROGGEN MARKUS
权利人:NALU BIO INC
摘要:Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((−)-trans-Δ9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

专利号:US-10981850-B2
优先权日:2019-04-15
标 题 :One-step flow-mediated synthesis of cannabidiol (CBD) and derivatives
发明人：PORCO JOHN A; BEELER AARON B; BROWN LAUREN E; TRILLES RICHARD V
权利人:UNIV BOSTON
摘要:Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.