1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

Base Information

• Chemical Name: 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one
• CAS No.: 1222190-49-9
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 1222190-49-9.mol

Synonyms:1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

Chemical Property of 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

There total 8 articles about 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one 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: 91.0%

2-((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide (1222190-44-4) + 3-chloroprop-1-ene (107-05-1) → 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9)

Guidance literature:

With magnesium; In tetrahydrofuran; ethylene dibromide; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201100888

Reference yield: 82.0%

2-((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide (1222190-44-4) + allylmagnesium bromide (2622-05-1) → 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2010.02.070

Reference yield:

Octanal (124-13-0) → 1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 36 h / -15 °C / Molecular sieve

2.1: ozone / dichloromethane / 0.08 h / -78 °C

2.2: 18 h / 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C

4.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C

With titanium(IV) isopropylate; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; magnesium; In tetrahydrofuran; dichloromethane; ethylene dibromide; toluene; 1.1: Keck allylation / 2.2: Wittig-Horner reaction;

DOI:10.1002/ejoc.201100888

upstream raw materials:

2-((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide

allylmagnesium bromide

(R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxydecan-1-one

(R,E)-5-hydroxy-N-methoxy-N-methyldodec-2-enamide

Downstream raw materials:

(R)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

(S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

(S,E)-6-[(2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]-5-hydroxy-N-methoxy-N-methylhex-2-enamide

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]-N-methoxy-N-methylacetamide