C₁₈H₁₅FO

Base Information

• Chemical Name: C₁₈H₁₅FO
• CAS No.: 1338236-50-2
• Molecular Formula: C₁₈H₁₅FO
• Molecular Weight: 266.315
• Mol file: 1338236-50-2.mol

Synonyms:

Chemical Property of C₁₈H₁₅FO

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₈H₁₅FO

There total 6 articles about C₁₈H₁₅FO 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:

6-fluoro-3,4-dihydro-1-methoxy-1H-isochromene (1032509-45-7) + 1-ethynyl-3-methyl-benzene (766-82-5) → C18H15FO + C18H15FO (1338236-50-2)

Guidance literature:

6-fluoro-3,4-dihydro-1-methoxy-1H-isochromene; 1-ethynyl-3-methyl-benzene; With Cu(MeCN)4PF₆; N-ethyl-N,N-diisopropylamine; (4S,4S')-(-)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(phenylmethyl)oxazole]; In diethyl ether; at -22 ℃; for 0.0833333h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -22 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja207585p

Reference yield:

3,4-dihydro-6-fluoro-1H-isochromene (50396-63-9) → C18H15FO + C18H15FO (1338236-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 24 h / 20 °C / Inert atmosphere

2.1: Cu(MeCN)4PF₆; N-ethyl-N,N-diisopropylamine; (4S,4S')-(-)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(phenylmethyl)oxazole] / diethyl ether / 0.08 h / -22 °C / Inert atmosphere

2.2: 12 h / -22 °C / Inert atmosphere

With Cu(MeCN)4PF₆; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (4S,4S')-(-)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(phenylmethyl)oxazole]; In diethyl ether; dichloromethane;

DOI:10.1021/ja207585p

Reference yield:

2-(3-fluorophenyl)ethanol (52059-53-7) → C18H15FO + C18H15FO (1338236-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid; lithium bromide / 24 h / Inert atmosphere; Reflux

2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 24 h / 20 °C / Inert atmosphere

4.1: Cu(MeCN)4PF₆; N-ethyl-N,N-diisopropylamine; (4S,4S')-(-)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(phenylmethyl)oxazole] / diethyl ether / 0.08 h / -22 °C / Inert atmosphere

4.2: 12 h / -22 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; Cu(MeCN)4PF₆; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (4S,4S')-(-)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(phenylmethyl)oxazole]; lithium bromide; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja207585p

upstream raw materials:

6-fluoro-3,4-dihydro-1-methoxy-1H-isochromene

1-ethynyl-3-methyl-benzene

3,4-dihydro-6-fluoro-1H-isochromene

2-(3-fluorophenyl)ethanol

Refernces

• 1、 Maity, Prantik,Srinivas, Harathi D.,Watson, Mary P.. "Copper-catalyzed enantioselective additions to oxocarbenium ions: Alkynylation of isochroman acetals". supporting information; experimental part. p. 17142 - 17145. Retrieved 2011/12/13.