dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Base Information

• Chemical Name: dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
• CAS No.: 100017-29-6
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 100017-29-6.mol

Synonyms:dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Chemical Property of dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

There total 5 articles about dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate 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:

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene (82045-04-3) + malonic acid dimethyl ester (108-59-8) → (E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate (200191-40-8) + dimethyl <1-phenyl-2(E)-butenyl>malonate (115404-72-3) + dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate (100017-29-6)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; bis(μ-trifluoroacetato)bis{(2,3,4,-η)-3-pentenyl}dipalladium; 2-<(1R)-2-endo-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>-1,10-phenanthroline; potassium acetate; In tetrahydrofuran; at 25 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja950860t

Reference yield:

malonic acid dimethyl ester (108-59-8) + ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate (163807-60-1) → (E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate (200191-40-8) + dimethyl <1-phenyl-2(E)-butenyl>malonate (115404-72-3) + dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate (100017-29-6)

Guidance literature:

With 2,6-bis((S)-1-((S)-2-isopropylaziridin-1-yl)(phenyl)methyl)pyridine; potassium acetate; bis-(trimethylsilyl)acetamide; In dichloromethane; at 25 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1002/adsc.200606109

Reference yield:

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene (82045-04-3) + malonic acid dimethyl ester (108-59-8) → dimethyl <1-phenyl-2(E)-butenyl>malonate (115404-72-3) + dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate (100017-29-6) + (R)-2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester (90383-10-1) + (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester (88057-04-9)

Guidance literature:

With sodium hydride; 4,5-bis[(2R,5R)-2,5-dimethylphospholanyl]-9,9-dimethylxanthene; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at 20 ℃; for 24h; Further Variations:; Reagents; Solvents; Reaction partners; time; Product distribution;

DOI:10.1002/ejic.200400312

upstream raw materials:

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

dimethyl malonate sodium salt

malonic acid dimethyl ester

ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate

Refernces

• 1、 Togni, Antonio. "Asymmetric Allylic Alkylation Catalyzed by Palladium-Sparteine Complexes". . p. 683 - 690. Retrieved 1991.
• 2、 Cheung, Hong Yee,Yu, Wing-Yiu,Au-Yeung, Terry T. L.,Zhou, Zhongyuan,Chan, Albert S. C.. "Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations". experimental part. p. 1412 - 1422. Retrieved 2009/12/22.