CAS: 80286-58-4; 2-((1R,4R,4As,8Ar)-4,7-Dimethyl-1,2,3,4,4A,5,6,8A-Octahydronaphthalen-1-yl)Acrylic Acid

该化合物是一种来自阿耳特西娅 Annua植物(通称甘草)的松树类植物(通称甘草)的松树化合物,是青蒿素(一种重要的抗疟药物)的前体,青蒿素化学配方为C15H22O4, 其特点是一个复杂的结构,包括双环框架和多种功能组,包括盒状酸和氢氧化物组;该化合物的特点是水溶性相对较低,但有机溶剂的溶性较高,这是许多树类的典型特征;青蒿酸展示生物活动,有助于植物的药性,并吸引人们对其在药物中的潜在应用感兴趣;其合成可以通过各种方法,包括植物的生物合成途径或实验室的化学合成方法实现;该化合物还研究其在通过生物技术方法生产青蒿素方面的作用,目的是提高抗疟药物生产的产量和可持续性.

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物理性质

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上下游产品

CAS号64-17-5 乙醇 | CAS号50-99-7 D(+)-无水葡萄糖 | CAS号63968-64-9 青蒿素 | CAS号50906-56-4 青蒿素B

合成工艺路线路线简述

  • 合成目标产物 Artemisic Acid 主要起始原料 Artemisinic Alcohol Impurity
  • 125184-95-4 = 80286-58-4
    反应条件:1.1 Reagents: Oxygen Catalysts: 2,2′-Bipyridine,4-(Dimethylamino)Pyridine,Tempo,Copper Bromide (Cubr) Solvents: Acetonitrile; 1 H,23 °C1.2 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol; 23 °C; 23 H,23 °C1.3 Reagents: Sodium Sulfite Solvents: Water; 5 Min,23 °C
    标题:Site-Selective Functionalization Of Unactivated Allylic C-H Bonds Via Direct Deprotonation With Ktmp: Application To The Formal Total Synthesis Of (+)-Artemisinin From Amorphadiene
    作者:Clanton,Nicholas A.; Et Al
    参考文献:Organic Letters 日期:2023 卷标:25(1) 页码:277-281]

    125184-95-4 = 80286-58-4
    反应条件:1.1 Reagents: Sodium Bicarbonate,Dess-Martin Periodinane Solvents: Dichloromethane; 3 H,0 °C1.2 Reagents: Sodium Thiosulfate Solvents: Water1.3 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol,Water; 25 °C; 2 H,25 °C
    标题:An Enantioselective Ambimodal Cross-Diels-Alder Reaction And Applications In Synthesis
    作者:Xu,Meng-Meng; Et Al
    参考文献:Nature Catalysis 日期:2021 卷标:4(10) 页码:892-900]

    82869-24-7 = 80286-58-4
    反应条件:1.1 Reagents: Potassium Hydroxide
    标题:Biosynthesis Of Arteannuin. Ii. Chemical Synthesis Of The Precursors [15-2H]- And [15-3H]-Arteannuic Acid
    作者:Xia,Zhiqiang; Et Al
    参考文献:Huaxue Xuebao 日期:1991 卷标:49(12) 页码:1514-17]

    82869-24-7 + 128-08-5 = 80286-58-4
    反应条件:1.1 -2.1 Reagents: Potassium Hydroxide,Borate(1-),Tetrahydro-T4-,Sodium
    标题:Biosynthesis Of Arteannuin. Ii. Chemical Synthesis Of The Precursors [15-2H]- And [15-3H]-Arteannuic Acid
    作者:Xia,Zhiqiang; Et Al
    参考文献:Huaxue Xuebao 日期:1991 卷标:49(12) 页码:1514-17]

    593-71-5 + 917-54-4 + 2743517-14-6 = 80286-58-4
    反应条件:1.1 Reagents: Lithium Bromide Solvents: Tetrahydrofuran; -78 °C; 1 H,-78 °C; -78 °C -> 25 °C; Overnight,25 °C1.2 Reagents: Lithium Iodide; 48 H,25 °C1.3 Reagents: Ammonium Chloride Solvents: Water; 0 °C2.1 Reagents: Sodium Bicarbonate,Dess-Martin Periodinane Solvents: Dichloromethane; 3 H,0 °C2.2 Reagents: Sodium Thiosulfate Solvents: Water2.3 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol,Water; 25 °C; 2 H,25 °C
    标题:An Enantioselective Ambimodal Cross-Diels-Alder Reaction And Applications In Synthesis
    作者:Xu,Meng-Meng; Et Al
    参考文献:Nature Catalysis 日期:2021 卷标:4(10) 页码:892-900]

    85031-59-0 = 80286-58-4
    反应条件:1.1 Reagents: Oxygen,Hydrazine Hydrate (1:1) Solvents: 1-Propanol; 25 Min,100 °C
    标题:Continuous Flow Reduction Of Artemisinic Acid Utilizing Multi-Injection Strategies-Closing The Gap Towards A Fully Continuous Synthesis Of Antimalarial Drugs
    作者:Pieber,Bartholomaeus; Et Al
    参考文献:Chemistry - A European Journal 日期:2015 卷标:21(11) 页码:4368-4376]

    125276-60-0 = 80286-58-4
    反应条件:1.1 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol,Water; 25 °C; 2 H,25 °C
    标题:An Enantioselective Ambimodal Cross-Diels-Alder Reaction And Applications In Synthesis
    作者:Xu,Meng-Meng; Et Al
    参考文献:Nature Catalysis 日期:2021 卷标:4(10) 页码:892-900]

    = 80286-58-4
    反应条件:1.1 Reagents: Potassium Hydroxide,Borate(1-),Tetrahydro-T4-,Sodium
    标题:Biosynthesis Of Arteannuin. Ii. Chemical Synthesis Of The Precursors [15-2H]- And [15-3H]-Arteannuic Acid
    作者:Xia,Zhiqiang; Et Al
    参考文献:Huaxue Xuebao 日期:1991 卷标:49(12) 页码:1514-17]

    59-23-4 = 80286-58-4
    反应条件:1.1 Solvents: Water; 120 H,30 °C
    标题:Production Of The Antimalarial Drug Precursor Artemisinic Acid In Engineered Yeast
    作者:Ro,Dae-Kyun; Et Al
    参考文献:Nature (London 日期:2006 卷标:440(7086) 页码:940-943]

    92692-39-2 = 80286-58-4
    反应条件:1.1 Catalysts: Cytochrome P450 Solvents: Water
    标题:A Chicory Cytochrome P450 Mono-Oxygenase Cyp71Av8 For The Oxidation Of (+)-Valencene
    作者:Cankar,Katarina; Et Al
    参考文献:Febs Letters 日期:2011 卷标:585(1) 页码:178-182]

    92692-39-2 = 80286-58-4
    反应条件:1.1 Reagents: Butyllithium,Potassium Tert-Butoxide Solvents: Tetrahydrofuran,Hexane; -78 °C; 15 Min,-78 °C1.2 Reagents: 2,2,6,6-Tetramethylpiperidine; -78 °C; 15 Min,-78 °C1.3 1 H,-78 °C1.4 Reagents: Triisopropyl Borate; 30 Min,-78 °C -> Rt1.5 Reagents: Hydrogen Peroxide Solvents: Water; < 30 °C; 30 Min,< 30 °C2.1 Reagents: Oxygen Catalysts: 2,2′-Bipyridine,4-(Dimethylamino)Pyridine,Tempo,Copper Bromide (Cubr) Solvents: Acetonitrile; 1 H,23 °C2.2 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol; 23 °C; 23 H,23 °C2.3 Reagents: Sodium Sulfite Solvents: Water; 5 Min,23 °C
    标题:Site-Selective Functionalization Of Unactivated Allylic C-H Bonds Via Direct Deprotonation With Ktmp: Application To The Formal Total Synthesis Of (+)-Artemisinin From Amorphadiene
    作者:Clanton,Nicholas A.; Et Al
    参考文献:Organic Letters 日期:2023 卷标:25(1) 页码:277-281]

    593-71-5 + 917-54-4 = 80286-58-4
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Overnight,60 °C1.2 Reagents: Oxalyl Chloride Solvents: Dimethylformamide,Dichloromethane; 0 °C; 1 H,0 °C; 0 °C -> 25 °C; 4 H,25 °C1.3 Reagents: Lithium Bromide Solvents: Tetrahydrofuran; -78 °C; 1 H,-78 °C; -78 °C -> 25 °C; Overnight,25 °C1.4 Reagents: Lithium Iodide; 48 H,25 °C1.5 Reagents: Ammonium Chloride Solvents: Water; 0 °C2.1 Reagents: Sodium Bicarbonate,Dess-Martin Periodinane Solvents: Dichloromethane; 3 H,0 °C2.2 Reagents: Sodium Thiosulfate Solvents: Water2.3 Reagents: 2-Methyl-2-Butene,Monosodium Phosphate,Sodium Chlorite Solvents: Tert-Butanol,Water; 25 °C; 2 H,25 °C
    标题:An Enantioselective Ambimodal Cross-Diels-Alder Reaction And Applications In Synthesis
    作者:Xu,Meng-Meng; Et Al
    参考文献:Nature Catalysis 日期:2021 卷标:4(10) 页码:892-900
📜在 戴斯-马丁氧化剂,Lithium Bromide,Sodium Hydroxide,Lithium Iodide体系中,用 甲醇 作为反应溶剂,化学反应生成 青蒿酸
参考文献:对映选择性双峰交叉diels-Alder反应及其在合成中的应用
标题:对映选择性双峰交叉diels-Alder反应及其在合成中的应用
摘要:与传统的 Diels-Alder 反应相比,两种不同共轭二烯之间的选择性交叉 Diels-Alder 反应的发展,特别是催化不对称方式的发展一直被忽略.我们现在报道了由铜 (II)-双(恶唑啉) 配合物催化的 3-烷氧基羰基-2-吡喃酮与未活化的共轭二烯的周围选择性和对映选择性交叉 Diels-Alder 反应,从而产生正式的反电子需求加合物在温和的反应条件下具有高对映选择性.计算研究表明,该反应通过双峰过渡态进行:过渡态后分叉导致具有相同对映选择性的 [2+4] 和 [4+2] 加合物,然后进行简单的 Cope 重排以提供单一观测到的热力学[2+4] 产品.顺式-双环支架.该反应的合成价值通过两种具有重要生物学意义的天然产物青蒿酸和冠状酸的不对称合成得到证明.
DOI:10.1038/s41929-021-00687-X

海关参考信息

专利信息


专利号:US-2025214918-A1
优先权日:2022-05-20
标 题:Functionalization of terpenes by selective deprotonation for the synthesis of (+)-artemisinin and related compounds
发明人：FRANTZ DOUG E; BLUMBERG SHAWN; ORTIZ ELIEZER; CLANTON NICHOLAS; WILSON NICK
权利人:UNIV TEXAS
摘要:The present invention provides methods for the preparation of (+)-Artemisinin and intermediates thereof, including via the regioselective deprotonation of amorphadiene (AD). In other aspects, there are provided methods for the functionalization terpenes by selective deprotonation, including the utilization of 4,11-amorphadiene as an industrially viable feedstock for the synthesis of artemisinin. In some embodiments, these methods are broadly applicable to the derivatization of a variety of cyclic and linear terpenes.

专利号:WO-2015030681-A1
优先权日:2013-08-30
标题:In vitro synthetic multi-biocatalytic system for the synthesis of isoprenoids and isoprenoid precursors
发明人：TOO HENG PHON; CHEN XIXIAN; ZOU RUIYANG; ZHANG CONQIANG
权利人:UNIV SINGAPORE
摘要:Disclosed herein are in vitro multi-biocatalytic systems for the synthesis of isoprenoid precursors and isoprenoids, as well as methods of producing isoprenoid precursors or isoprenoids in vitro using the systems disclosed herein.

专利号:US-11384367-B2
优先权日:2016-12-22
标题:Synthesis of bioproducts from lignin-derived aromatics by genetically modified microorganisms
发明人：GLADDEN JOHN M; SKERKER JEFFREY M; KEASLING JAY D; KIRBY JAMES; YAEGASHI JUNKO
权利人:UNIV CALIFORNIA; NAT TECH & ENG SOLUTIONS SANDIA LLC; BATTELLE MEMORIAL INSTITUTE FOR MANAGEMENT AND OPERATION OF PACIFIC NORTHWEST NAT LABORATORY; NATIONAL TECH AND ENGINEERING SOLUTIONS OF SANDIA LLC
摘要:The present invention provides for a method of converting a depolymerized lignin aromatic compound into a bioproduct, comprising: (a) providing a composition comprising a depolymerized lignin aromatic compound, optionally a depolymerized cellulose, and optionally a depolymerized hemicellulose, and (b) introducing a genetically modified microorganism to the composition, wherein the genetically modified microorganism is capable of converting the depolymerized lignin aromatic compound into a bioproduct; such that the depolymerized lignin aromatic compound is converted into a bioproduct.

专利号:WO-2020121335-A1
优先权日:2018-12-14
标题:A process for producing tirucalladienol for synthesis of limonoids
发明人：HIREKODATHAKALLU VENKATARAMAIAH THULASIRAM; PANDREKA AVINASH; PATIL CHAYA SHIVANAGOUDA
权利人:COUNCIL SCIENT IND RES
摘要:The invention relates to the construction of recombinant DNA constructs encoding tirucalladienol synthase; and squalene epoxidase operably linked to a regulatory sequence. The production of tricualldienol in a yeast is increased by coexpression with squalene epoxidase. Further, tirucalladeinol synthase engineering leads to increase in the efficiency of the synthesis process towards tirucalladienol.

专利号:WO-2014052054-A1
优先权日:2012-09-25
标题 :Enzymatic platform for the synthesis of isoprenoid precursors and uses thereof
发明人：LEYH THOMAS S
权利人:EINSTEIN COLL MED
摘要:Provided are method of synthesizing (R)-5-diphosphomevalonate (DPM), isopentenyl 5-pyrophosphase (IPP), dimethylallyl 5 -pyrophosphate (DMAPP) and isoprenoid using a one-pot synthesis.

专利号:US-7541172-B2
优先权日:1998-08-27
标题:Transgenic amorpha-4, 11-diene synthesis
发明人：WALLAART THORVALD EELCO; BOUWMEESTER HENDRIK JAN
权利人:INST ONEWORLD HEALTH
摘要:The present invention relates to an isolated DNA sequence encoding a polypeptide having the biological activity of amorpha-4,11-diene synthase. This DNA sequence can be used for the transformation of bacteria, yeasts and plants for the production of amorpha-4,11-diene, a specific precursor in the synthesis of artemisinin, in the respective organisms. The invention also relates to these organisms.

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合成参考文献


摘要:Quin, M. B.; Flynn, C. M.; Ellinger, J. J.; Schmidt-Dannert, C., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 369.
参考文献:10.1186/s12934-021-01641-z
摘要:Xu L, Liu P, Dai Z, Fan F, Zhang X. Fine-tuning the expression of pathway gene in yeast using a regulatory library formed by fusing a synthetic minimal promoter with different Kozak variants. Microbial Cell Factories. 2021 Jul 28;20(1):148. doi: 10.1186/s12934-021-01641-z.
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