Diethyl 2-pent-4-enylpropanedioate

Base Information

• Chemical Name: Diethyl 2-pent-4-enylpropanedioate
• CAS No.: 1906-96-3
• Molecular Formula: C12H20 O4
• Molecular Weight: 228.288
• Hs Code.: 2917190090
• NSC Number: 624962
• DSSTox Substance ID: DTXSID10326980
• Nikkaji Number: J2.044.397I
• Wikidata: Q82088258
• Mol file: 1906-96-3.mol

Synonyms:diethyl 2-pent-4-enylpropanedioate;1906-96-3;DIETHYL 4-PENTENYLMALONATE;NSC624962;diethyl 2-(pent-4-enyl)malonate;diethyl (4-pentenyl)-malonate;Diethyl 2-(4-pentenyl)malonate;diethyl pent-4-enylmalonate;diethyl (4-pentenyl)malonate;SCHEMBL2207325;DTXSID10326980;AKOS017549511;(4-Pentenyl)malonic acid diethyl ester;NSC-624962;2-Pent-4-enyl-malonic acid diethyl ester

Chemical Property of Diethyl 2-pent-4-enylpropanedioate

Chemical Property:

• PSA: 52.60000
• LogP: 2.08510
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 228.13615911
• Heavy Atom Count: 16
• Complexity: 217

Purity/Quality:

98%,99%, ^*data from raw suppliers

DIETHYL 4-PENTENYLMALONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCCC=C)C(=O)OCC

Technology Process of Diethyl 2-pent-4-enylpropanedioate

There total 14 articles about Diethyl 2-pent-4-enylpropanedioate 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: 86.0%

bromopentene (1119-51-3) + diethyl malonate (105-53-3) → diethyl (4-pentenyl)malonate (1906-96-3)

Guidance literature:

With sodium; In ethanol; for 3h; Heating;

DOI:10.1021/ja00368a014

Reference yield: 78.0%

diethyl cyclopropane-1,1-dicarboxylate (1559-02-0) + allyl-trimethyl-silane (762-72-1) → diethyl (4-pentenyl)malonate (1906-96-3)

Guidance literature:

With ethylaluminum dichloride; In dichloromethane; at 0 ℃;

DOI:10.1039/c39880000734

Reference yield: 67.0%

bromopentene (1119-51-3) + diethyl malonate (105-53-3) → diethyl (4-pentenyl)malonate (1906-96-3) + diethyl 2,2-di-(4-pentenyl) malonate (519179-68-1)

Guidance literature:

diethyl malonate; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

bromopentene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1055/s-0032-1317020

upstream raw materials:

sodium diethylmalonate

bromopentene

diethyl cyclopropane-1,1-dicarboxylate

lithium dilallyl cuprate

Downstream raw materials:

diethyl (E)-2-(5-phenylpent-4-enyl)malonate

ethyl 6-heptenoate

(+/-)-trans-2-methyl-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester

C₃₄H₅₀O₁₀

Refernces

• 1、 Bambal, Ramesh,Kemmitt, Raymond D. W.. "Conjugate Addition of Allyltrimethylsilane to Electrophilic Cyclopropanes". . p. 734 - 735. Retrieved 1988.
• 2、 -. "CYCLOBUTANE- AND AZETIDINE-CONTAINING MONO AND SPIROCYCLIC COMPOUNDS AS ALPHA V INTEGRIN INHIBITORS". Page/Page column 265; 287-289. . Retrieved 2018/05/27.
• 3、 Kotha, Sambasivarao,Shirbhate, Mukesh E.. "A general synthetic approach to para-cyclophanes via ring-closing metathesis". . p. 1483 - 1494. Retrieved 2016/02/26.