Artemisinic alcohol

Base Information

• Chemical Name: Artemisinic alcohol
• CAS No.: 125184-95-4
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• DSSTox Substance ID: DTXSID201315937
• Metabolomics Workbench ID: 63498
• Nikkaji Number: J1.519.059K
• Wikidata: Q27133422
• Mol file: 125184-95-4.mol

Synonyms:Artemisinic alcohol;125184-95-4;(+)-artemisinic alcohol;Artemisinic Alcohol Impurity;amorpha-4,11-diene-12-ol;2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-en-1-ol;Arteannuic alcohol;amorpha-4,11-dien-12-ol;SCHEMBL14189186;CHEBI:64783;DTXSID201315937;C20307;Q27133422

Chemical Property of Artemisinic alcohol

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 303

Purity/Quality:

98% ^*data from raw suppliers

ArtemisinicAlcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(C2C1CCC(=C2)C)C(=C)CO
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H]2[C@H]1CCC(=C2)C)C(=C)CO
• Uses: Artemisinic Alcohol is a compound that may be useful for semi-synthesis of?Artemisinin (A777500), which is an effective antimalarial agent used to treat malaria.

Technology Process of Artemisinic alcohol

There total 14 articles about Artemisinic alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

methyl artemisinate (82869-24-7) → dehydroartemisinyl alcohol (125184-95-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(01)00641-4

Reference yield: 65.0%

artemisinic acid (80286-58-4) → dehydroartemisinyl alcohol (125184-95-4)

Guidance literature:

artemisinic acid; With lithium aluminium tetrahydride; In tetrahydrofuran; at 70 ℃; for 15h; Heating / reflux;

With sodium hydroxide; water; In tetrahydrofuran; for 0.166667h;

Reference yield: 20.0%

(1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (92692-39-2) + trifluoroacetic acid (76-05-1) → C17H23F3O2 + dehydroartemisinyl alcohol (125184-95-4)

Guidance literature:

With palladium(II) trifluoroacetate; silver trifluoroacetate; p-benzoquinone; In dimethyl sulfoxide; acetonitrile; at 80 ℃; for 19h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c00653

upstream raw materials:

methyl artemisinate

(1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

artemisinic acid

diazomethane

Downstream raw materials:

artemisinic acid

artemisinic aldehyde

Refernces

• 1、 Cai, Quan,Chen, Xiangyang,Houk, K. N.,Lu, Qi-Tao,Tan, Kui,Xu, Meng-Meng,Yang, Limin. "An enantioselective ambimodal cross-Diels–Alder reaction and applications in synthesis". . p. 892 - 900. Retrieved 2021/10/20.
• 2、 -. "POLYNUCLEOTIDES ENCODING ISOPRENOID MODIFYING ENZYMES AND METHODS OF USE THEREOF". Page/Page column 48. . Retrieved 2008/06/13.