(R)-1,2-Dihydroacenaphthylen-1-amine

Base Information

• Chemical Name: (R)-1,2-Dihydroacenaphthylen-1-amine
• CAS No.: 228246-73-9
• Molecular Formula: C12H11N
• Molecular Weight: 169.226
• DSSTox Substance ID: DTXSID50708488
• Wikidata: Q82642839
• Mol file: 228246-73-9.mol

Synonyms:(R)-1,2-Dihydroacenaphthylen-1-amine;228246-73-9;(R)-1,2-Dihydroacenaphthene-1-amine;(1R)-1,2-DIHYDROACENAPHTHYLEN-1-AMINE;(R)-Acenaphthen-1-yl-amine;SCHEMBL2244164;DTXSID50708488;LCYNDXQWJAMEAI-LLVKDONJSA-N;AKOS015998850

Chemical Property of (R)-1,2-Dihydroacenaphthylen-1-amine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 335.543°C at 760 mmHg
• Flash Point: 173.935°C
• PSA: 26.02000
• Density: 1.188g/cm³
• LogP: 3.09600
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 169.089149355
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

97% ^*data from raw suppliers

(R)-1,2-Dihydroacenaphthene-1-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=CC=CC3=C2C1=CC=C3)N
• Isomeric SMILES: C1[C@H](C2=CC=CC3=C2C1=CC=C3)N
• Uses: (R)-1,2-Dihydroacenaphthene-1-amine is an intermediate in the synthesis of W 212393 (W400090), a small-molecule opioid receptor-like 1 (ORL1) receptor agonist.

Technology Process of (R)-1,2-Dihydroacenaphthylen-1-amine

There total 2 articles about (R)-1,2-Dihydroacenaphthylen-1-amine 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:

1-aminoacenaphthene (40745-44-6) → (R)-1-Acenaphthylamine (228246-73-9) + (S)-1-Acenaphthylamine (228246-74-0) + 1(2H)-acenaphthylenone (2235-15-6)

Guidance literature:

With pyridoxal 5'-phosphate; transaminase-9; piruvate; In dimethyl sulfoxide; at 30 ℃; pH=9; Reagent/catalyst; enantioselective reaction; Enzymatic reaction;

DOI:10.1038/nchem.2578

Reference yield:

acenaphthen-1-yl-dimethyl-borane → (R)-1-Acenaphthylamine (228246-73-9) + (S)-1-Acenaphthylamine (228246-74-0)

Guidance literature:

With hydroxylamine-O-sulfonic acid; In tetrahydrofuran; for 10h; Title compound not separated from byproducts;

Reference yield:

(R)-1-Acenaphthylamine (228246-73-9) → 1-(R)-Acenaphthen-1-yl-4-(formyl-phenyl-amino)-piperidine-4-carboxylic acid amide

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / ethanol / Heating

2: AcOH / Ambient temperature

3: 1.) Ac₂O, 2.) formic acid, AcOH / 1.) RT, 2.) RT

With formic acid; acetic anhydride; potassium carbonate; acetic acid; In ethanol;

DOI:10.1016/S0960-894X(99)00385-6

upstream raw materials:

1-aminoacenaphthene

Downstream raw materials:

(R)-1-(acenaphthen-1-yl)-piperidine-4-one

(R)-4-phenylamino-1-(acenaphthen-1-yl)-piperidine4-carbonitrile