diethyl (3-methylbut-2-enyl)malonate

Base Information

• Chemical Name: diethyl (3-methylbut-2-enyl)malonate
• CAS No.: 22539-80-6
• Molecular Formula: C12H20 O4
• Molecular Weight: 228.288
• Hs Code.: 2917190090
• European Community (EC) Number: 245-067-9
• UNII: YJ45VSJ5KL
• DSSTox Substance ID: DTXSID00177064
• Nikkaji Number: J286.240I
• Mol file: 22539-80-6.mol

Synonyms:Malonicacid, (3-methyl-2-butenyl)-, diethyl ester (7CI,8CI); Propanedioic acid,(3-methyl-2-butenyl)-, diethyl ester (9CI); (3,3-Dimethylallyl)malonic aciddiethyl ester; (3-Methyl-2-butenyl)propanedioic acid diethyl ester; Diethyl2-(3-methyl-2-butenyl)malonate; Diethyl 3-methyl-2-butenylmalonate; Diethylprenylmalonate; Ethyl 2-carbethoxy-5-methyl-4-hexenoate

Chemical Property of diethyl (3-methylbut-2-enyl)malonate

Chemical Property:

• Vapor Pressure: 0.0216mmHg at 25°C
• Boiling Point: 250.5°Cat760mmHg
• PKA: 12.69±0.59(Predicted)
• Flash Point: 109.2°C
• PSA: 52.60000
• Density: 1.003g/cm³
• LogP: 2.08510
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 228.13615911
• Heavy Atom Count: 16
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC=C(C)C)C(=O)OCC
• Uses: Diethyl 2-Prenylmalonate is an intermediate in the synthesis of Feprazone (F285650), an anti-inflammatory agent used in the management of inflammatory or degenerative joint diseases.

Technology Process of diethyl (3-methylbut-2-enyl)malonate

There total 52 articles about diethyl (3-methylbut-2-enyl)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: 97.0%

prenyl bromide (870-63-3) + diethyl malonate (105-53-3) → diethyl (3-methylbut-2-enyl)malonate (22539-80-6)

Guidance literature:

DOI:10.1016/S0040-4020(01)80336-7

Reference yield: 81.0%

diethyl malonate (105-53-3) + 3,3-dimethyl-allyl chloride (503-60-6) → diethyl (3-methylbut-2-enyl)malonate (22539-80-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 30 min; 2.) RT, 2 h;

DOI:10.1016/S0040-4039(00)73498-8

Reference yield: 75.0%

prenyl bromide (870-63-3) + diethyl malonate (105-53-3) → diethyl (3-methylbut-2-enyl)malonate (22539-80-6) + diethyl 2,2-bis(3-methylbut-2-en-1-yl)malonate (97037-74-6)

Guidance literature:

diethyl malonate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

prenyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02492

upstream raw materials:

sodium diethylmalonate

prenyl bromide

1,3-dibromo-3-methylbutane

diethyl methylenemalonate

Downstream raw materials:

diethyl 4,4-dimethyl-3-(prop-1-en-2-yl)cyclohexane-1,1-dicarboxylate

diethyl 2,2-bis(3-methylbut-2-en-1-yl)malonate

diethyl 4-phenylcyclohex-3-ene-1,1-dicarboxylate

4-methylcyclohex-3-ene-1,1-dicarboxylic acid diethyl ester

Refernces

• 1、 Kawasaki, Masashi,Shimizu, Momo,Kuroyanagi, Saki,Shishido, Yoshiaki,Komiyama, Tsuyoshi,Toyooka, Naoki. "Syntheses and odor properties of optically active dimethyl octenone and its analogs". . p. 285 - 293. Retrieved 2016.
• 2、 Kim, Junsu,Lee, Da Hye,Kim, Jinho. "Copper-Catalyzed Aerobic Oxidative Azo-Ene Cyclization". supporting information. p. 4728 - 4733. Retrieved 2021/09/09.
• 3、 Chen, Chao,Hao, Yu,Zhang, Ting-Yu,Pan, Jin-Long,Ding, Jun,Xiang, Heng-Ye,Wang, Man,Ding, Tong-Mei,Duan, Abing,Zhang, Shu-Yu. "Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes". supporting information. p. 755 - 758. Retrieved 2019/01/21.