1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone

Base Information

• Chemical Name: 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone
• CAS No.: 871838-08-3
• Molecular Formula: C₃₁H₃₆N₂O₂
• Molecular Weight: 468.639
• Mol file: 871838-08-3.mol

Synonyms:1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone

Chemical Property of 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone

There total 17 articles about 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone 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: 67.0%

1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-prop-2-yn-1-ol (871838-14-1) → 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone (871838-08-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol0521228

Reference yield: 37.0%

6'-(3-benzyloxy-propyl)-6,2'-diisobutyl[2,3']bipyridinyl-5-carboxylic acid ethyl ester (871838-05-0) + acetylenemagnesium bromide (4301-14-8) → 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone (871838-08-3)

Guidance literature:

With N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; at -5 - 20 ℃; for 24h;

DOI:10.1021/ol0521228

Reference yield:

4-benzyloxybutanal (5470-84-8) → 1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone (871838-08-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 54 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

2.1: 79 percent / CrO₃; H₂SO₄ / acetone; H₂O / 0.67 h / 0 °C

3.1: ammonium acetate / toluene / 1 h / Heating

3.2: 65 percent / ytterbium(III) triflate / toluene / 48 h / Heating

4.1: 82 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

5.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

6.1: 89 percent / tetrahydrofuran / -78 - 0 °C

7.1: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

8.1: ammonium acetate / toluene / 1 h / Heating

8.2: 78 percent / ytterbium(III) triflate / toluene / 48 h / Heating

9.1: 78 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

10.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

11.1: 53 percent / tetrahydrofuran / -78 - 0 °C

12.1: 67 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

With chromium(VI) oxide; ammonium acetate; manganese(IV) oxide; oxalyl dichloride; sulfuric acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 2.1: Jones oxidation / 3.2: Bohlmann-Rahtz heteroannulation / 5.1: Swern oxidation / 8.2: Bohlmann-Rahtz heteroannulation / 10.1: Swern oxidation;

DOI:10.1021/ol0521228

upstream raw materials:

1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-prop-2-yn-1-ol

6'-(3-benzyloxy-propyl)-6,2'-diisobutyl[2,3']bipyridinyl-5-carboxylic acid ethyl ester

acetylenemagnesium bromide

6-(3-benzyloxy-propyl)-2-isobutyl-pyridine-3-carbaldehyde

Downstream raw materials:

6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester