Hydrohydrastinine

Base Information

• Chemical Name: Hydrohydrastinine
• CAS No.: 494-55-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Hs Code.: 2934999090
• European Community (EC) Number: 207-792-9
• NSC Number: 112975
• UNII: 7UYL6N5J89
• DSSTox Substance ID: DTXSID80197785
• Nikkaji Number: J6.078J
• Wikidata: Q27268880
• Metabolomics Workbench ID: 126917
• ChEMBL ID: CHEMBL2140445
• Mol file: 494-55-3.mol

Synonyms:Hydrohydrastinine;494-55-3;Hydrohydrastinin;6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline;6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline;UNII-7UYL6N5J89;MLS002706489;7UYL6N5J89;CHEMBL2140445;EINECS 207-792-9;NSC-112975;5,6,7,8-Tetrahydro-6-methyl-1,3,dioxolo[4,5-g]isoquinoline;5,6,7,8-TETRAHYDRO-6-METHYL-1,3,DIOXOLO(4,5-G)ISOQUINOLINE;HYDROHYDRASTININE [MI];SCHEMBL1760693;DTXSID80197785;BDBM50006638;Norhydrastinine,2-dihydro-2-methyl-;NSC112975;NSC788829;AKOS016008780;NSC 112975;NSC-788829;NCGC00246722-01;SMR001573894;1,5-g]isoquinoline, 5,6,7,8-tetrahydro-6-methyl-;Q27268880;1,3-Dioxolo[4,5-g]isoquinoline, 5,6,7,8-tetrahydro-6-methyl-

Chemical Property of Hydrohydrastinine

Chemical Property:

• Vapor Pressure: 0.000899mmHg at 25°C
• Melting Point: 66°
• Refractive Index: 1.5220 (estimate)
• Boiling Point: 304°Cat760mmHg
• PKA: 8.15±0.20(Predicted)
• Flash Point: 123°C
• PSA: 21.70000
• Density: 1.206g/cm³
• LogP: 1.34110
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C1)OCO3

Technology Process of Hydrohydrastinine

There total 53 articles about Hydrohydrastinine 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: 80.0%

6-methyl[1,3]dioxolo[4,5-g]isoquinoline-5,7(6H,8H)-dione (65628-87-7) → N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (494-55-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 5h; Reflux;

DOI:10.1055/s-0036-1588920

Reference yield: 72.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3,4-methylenedioxyphenylethylamine (1484-85-1) → N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (494-55-3)

Guidance literature:

With formic acid; In water; at 20 - 100 ℃; for 2h;

DOI:10.1021/jm4013592

Reference yield: 48.0%

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline (94143-83-6) + methyl iodide (74-88-4) → N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (494-55-3)

Guidance literature:

With potassium carbonate; Reflux;

DOI:10.1002/cmdc.201300332

upstream raw materials:

piperonal

2,2-diethoxy-ethanamine

hydrastinine

formaldehyd

Downstream raw materials:

1,2,3,4-tetrahydro-2-methylisoquinolin-7-ol

Oxyhydrastinine

5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline

1-(3,4,5-trimethoxyphenyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Jangir, Ravi,Argade, Narshinha P.. "Total Synthesis of Tetrahydroisoquinoline-Based Bioactive Natural Products Laudanosine, Romneine, Glaucine, Dicentrine, and Their Unnatural Analogues Isolaudanosine and Isoromneine". . p. 1655 - 1663. Retrieved 2017/03/21.
• 2、 Crestey, Fran?ois,Jensen, Anders A.,Borch, Morten,Andreasen, Jesper Tobias,Andersen, Jacob,Balle, Thomas,Kristensen, Jesper Langgaard. "Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists". supporting information. p. 9673 - 9682. Retrieved 2014/01/06.