2-Methallylmalonic acid dimethyl ester

Base Information

• Chemical Name: 2-Methallylmalonic acid dimethyl ester
• CAS No.: 50598-40-8
• Molecular Formula: C9H14O4
• Molecular Weight: 186.208
• Hs Code.: 2917190090
• Mol file: 50598-40-8.mol

Synonyms:dimethyl 2-methylprop-2-enylmalonate;

Chemical Property of 2-Methallylmalonic acid dimethyl ester

Chemical Property:

• PSA: 52.60000
• LogP: 0.91480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Methallylmalonic acid dimethyl ester

There total 16 articles about 2-Methallylmalonic acid dimethyl ester 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: 85.0%

2-methyl-3-bromo-1-propene (1458-98-6) + malonic acid dimethyl ester (108-59-8) → dimethyl (2-methyl-2-propenyl)-propanedioate (50598-40-8)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

2-methyl-3-bromo-1-propene; for 15h; Heating;

DOI:10.1016/S0040-4039(02)02594-7

Reference yield: 76.0%

2-methylprop-2-ene-1-sulfonyl chloride (14568-34-4) + malonic acid dimethyl ester (108-59-8) → dimethyl (2-methyl-2-propenyl)-propanedioate (50598-40-8)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

2-methylprop-2-ene-1-sulfonyl chloride; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 0.5h; regioselective reaction;

DOI:10.1016/j.tet.2008.11.007

Reference yield: 74.0%

malonic acid dimethyl ester (108-59-8) + 3-Chloro-2-methylpropene (563-47-3) → dimethyl (2-methyl-2-propenyl)-propanedioate (50598-40-8) + dimethyl 2,2-di(2-methylallyl)malonate (74793-47-8)

Guidance literature:

malonic acid dimethyl ester; With sodium methylate; potassium iodide; In methanol; at 20 ℃; for 1h; Inert atmosphere;

3-Chloro-2-methylpropene; In methanol; at 20 ℃; Reflux; Inert atmosphere;

upstream raw materials:

malonic acid dimethyl ester

3-Chloro-2-methylpropene

1-(phenylsulfonyl)-2-methyl-2-propene

dimethyl malonate sodium salt

Downstream raw materials:

2-<2-(phenylsulfonyl)buta-2,3-dienyl>-2-(2-methylallyl)malonic acid dimethyl ester

dimethyl 3-methylcyclohexane-1,1-dicarboxylate

C₉H₁₆O₂

C₂₀H₂₅NO₅

Refernces

• 1、 Zidan, Montserrat,McCallum, Terry,Swann, Rowan,Barriault, Louis. "Formal Bromine Atom Transfer Radical Addition of Nonactivated Bromoalkanes Using Photoredox Gold Catalysis". supporting information. p. 8401 - 8406. Retrieved 2020/11/03.
• 2、 Shu, Xing-Zhong,Schienebeck, Casi M.,Li, Xiaoxun,Zhou, Xin,Song, Wangze,Chen, Lianqing,Guzei, Ilia A.,Tang, Weiping. "Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene". supporting information. p. 5128 - 5131. Retrieved 2015/11/03.