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

Base Information

• Chemical Name: 5,6,7,8-Tetrahydro-6-methyl-5-(phenylmethyl)-1,3-dioxolo[4,5-g]isoquinoline
• CAS No.: 4514-05-0
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.354
• DSSTox Substance ID: DTXSID901142858
• Mol file: 4514-05-0.mol

Synonyms:DTXSID901142858;5,6,7,8-Tetrahydro-6-methyl-5-(phenylmethyl)-1,3-dioxolo[4,5-g]isoquinoline;4514-05-0

Chemical Property of 5,6,7,8-Tetrahydro-6-methyl-5-(phenylmethyl)-1,3-dioxolo[4,5-g]isoquinoline

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 281.141578849
• Heavy Atom Count: 21
• Complexity: 355

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C1CC4=CC=CC=C4)OCO3

Technology Process of 5,6,7,8-Tetrahydro-6-methyl-5-(phenylmethyl)-1,3-dioxolo[4,5-g]isoquinoline

There total 5 articles about 5,6,7,8-Tetrahydro-6-methyl-5-(phenylmethyl)-1,3-dioxolo[4,5-g]isoquinoline 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: 69.0%

tert-butyl 5-benzyl-7,8-dihydro[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate → 5-benzyl-6-methyl-2H,5H,6H,7H,8H-[1,3]-dioxolo[4,5-g]-isoquinoline (4514-05-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 17h; Inert atmosphere; Reflux;

DOI:10.1039/c6ob00577b

Reference yield:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline (94143-83-6) → 5-benzyl-6-methyl-2H,5H,6H,7H,8H-[1,3]-dioxolo[4,5-g]-isoquinoline (4514-05-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water; 1,4-dioxane / 20 h / 0 - 20 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.07 h / -50 °C

2.2: 16 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; 1,4-dioxane; hexane; water;

DOI:10.1039/c6ob00577b

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) → 5-benzyl-6-methyl-2H,5H,6H,7H,8H-[1,3]-dioxolo[4,5-g]-isoquinoline (4514-05-0)

Guidance literature:

With formic acid; at 180 ℃; im Rohr;

upstream raw materials:

formaldehyd

benzylmagnesium chloride

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

Downstream raw materials:

1-benzyl-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

1-benzyl-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol