(S)-4-(3-hydroxyhex-5-enyl)phenyl acetate

Base Information

• Chemical Name: (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate
• CAS No.: 1172115-59-1
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 1172115-59-1.mol

Synonyms:(S)-4-(3-hydroxyhex-5-enyl)phenyl acetate

Chemical Property of (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate

There total 5 articles about (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate 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: 53.0%

4-(3-oxopropyl)phenyl acetate (91143-05-4) + (1R,2R)-2-exo-hydroxy-2-endo-allyl-1,7,7-trimethylbicyclo<2.2.1>heptane (2371-43-9) → (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate (1172115-59-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; optical yield given as %ee;

DOI:10.1016/j.tetlet.2009.03.154

Reference yield: 44.0%

titanium(IV) isopropylate (546-68-9) + 4-(3-oxopropyl)phenyl acetate (91143-05-4) + allyltributylstanane (24850-33-7) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate (1172115-59-1)

Guidance literature:

titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; With trifluoroacetic acid; In dichloromethane; for 4h; Inert atmosphere; Reflux; Molecular sieve;

4-(3-oxopropyl)phenyl acetate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

allyltributylstanane; In dichloromethane; at -78 - -20 ℃; for 72h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetlet.2016.06.102

Reference yield:

3-(4-hydroxy-phenyl)-propionic acid ethyl ester (23795-02-0) → (S)-4-(3-hydroxyhex-5-enyl)phenyl acetate (1172115-59-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 4 h / Inert atmosphere; Reflux; Molecular sieve

4.2: 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

4.3: 72 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

With dmap; lithium aluminium tetrahydride; triethylamine; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 4.1: |Keck Asymmetric Allylation / 4.2: |Keck Asymmetric Allylation / 4.3: |Keck Asymmetric Allylation;

DOI:10.1016/j.tetlet.2016.06.102

upstream raw materials:

4-(3-oxopropyl)phenyl acetate

(1R,2R)-2-exo-hydroxy-2-endo-allyl-1,7,7-trimethylbicyclo<2.2.1>heptane

titanium(IV) isopropylate

allyltributylstanane

Downstream raw materials:

C₂₆H₂₉FO₈

C₂₈H₃₂O₁₀

(1S,3R,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

(1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

Refernces

• 1、 Parker, Gregory D.,Seden, Peter T.,Willis, Christine L.. "Synthesis of a novel diarylheptanoid isolated from Zingiber officinale". scheme or table. p. 3686 - 3689. Retrieved 2009/10/04.