Deoxoartemisinin

Base Information

• Chemical Name: Deoxoartemisinin
• CAS No.: 126189-95-5
• Molecular Formula: C15H24 O4
• Molecular Weight: 268.353
• Nikkaji Number: J304.249I
• ChEMBL ID: CHEMBL273441
• Mol file: 126189-95-5.mol

Synonyms:10-deoxoartemisinin;artemisinin, 10-deoxo;deoxoartemisinin;deoxodeoxyartemisinin;deoxoqinghaosu

Chemical Property of Deoxoartemisinin

Chemical Property:

• Vapor Pressure: 0.000305mmHg at 25°C
• Boiling Point: 373°Cat760mmHg
• Flash Point: 179.4°C
• PSA: 47.92000
• Density: 1.15g/cm³
• LogP: 2.42440
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 268.16745924
• Heavy Atom Count: 19
• Complexity: 386

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(COC3C24C1CCC(O3)(OO4)C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H](CO[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C

Technology Process of Deoxoartemisinin

There total 48 articles about Deoxoartemisinin 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: 71.0%

artemisinin (63968-64-9,113472-97-2,119241-68-8) → (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; for 0.166667h; Heating;

DOI:10.1021/jm00167a036

Reference yield: 69.0%

2-(5,9-dimethyl-10,11,13-trioxatricyclo[7.2.2.01,6]tridec-2-yl)propan-1-ol (613233-67-3) → (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; at 20 ℃; Reagent/catalyst; Temperature;

DOI:10.1002/chem.201300076

Reference yield: 32.0%

2-(5,9-dimethyl-10,11,13-trioxatricyclo[7.2.2.01,6]tridec-2-yl)propan-1-ol (613233-67-3) + bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9) → C17H25F3O5 + (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With iodine; In cyclohexane; at 20 ℃; for 35h;

DOI:10.1002/chem.201300076

upstream raw materials:

4-((4R,4aS,7R)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one

artemisinin

C₁₂H₁₃O₂(CH₃)3(O)(OO)

4-((4R,4aS,7R,8S)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one

Downstream raw materials:

artemisinin

C₁₂H₁₃O₂(CH₃)3(O)(OO)

1-oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanol formyl ester]-cyclohexane

(-)-deoxodesoxyartemisinin

Refernces

• 1、 Laurent, Sophie A.-L.,Robert, Anne,Meunier, Bernard. "C1O-modified artemisinin derivatives: Efficient heme-alkylating agents". . p. 2060 - 2063. Retrieved 2005.
• 2、 Wang, Kang-Kyun,Choi, Kyoung-Hoon,Shin, Hee-Won,Kim, Bong-Jin,Im, Ji-Eun,Oh, Seung-Lim,Park, Nam-Soo,Jung, Mankil,Oh, Jae-Buem,Lee, Myung-Jun,Kim, Hwan-Kyu,Kim, Yong-Rok. "Photophysics of a new photosensitizer with high quantum yield of singlet oxygen generation and its application to stereo-selective synthesis of (+)-deoxoartemisinin". experimental part. p. 81 - 86. Retrieved 2010/05/19.