Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate

Base Information

• Chemical Name: Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate
• CAS No.: 81937-39-5
• Molecular Formula: C18H23NO6
• Molecular Weight: 349.384
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60516556
• Mol file: 81937-39-5.mol

Synonyms:Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate;81937-39-5;diethyl 2-[1-(4-acetamidophenyl)-1-oxopropan-2-yl]propanedioate;diethyl2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate;SCHEMBL5369222;DTXSID60516556;DDOHSQHYRPGUIN-UHFFFAOYSA-N;AKOS016005230;DS-3961;SB83546;CS-0141831;C76625;A864477;Diethyl [1-(4-acetamidophenyl)-1-oxopropan-2-yl]propanedioate;Ethyl 4-(4-acetylaminophenyl)-2-(ethoxycarbonyl)-3-methyl-4-oxobutanoate

Chemical Property of Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate

Chemical Property:

• PSA: 102.26000
• LogP: 2.85570
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 349.15253745
• Heavy Atom Count: 25
• Complexity: 478

Purity/Quality:

99% ^*data from raw suppliers

Diethyl2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(C)C(=O)C1=CC=C(C=C1)NC(=O)C)C(=O)OCC

Technology Process of Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-yl)malonate

There total 5 articles about Diethyl 2-(1-(4-acetamidophenyl)-1-oxopropan-2-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: 87.4%

N-(4-(2-bromopropionyl)phenyl)acetamide (63514-63-6) + diethyl malonate (105-53-3) → 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester (81937-39-5)

Guidance literature:

diethyl malonate; With sodium hydride; In tetrahydrofuran; cooling;

N-(4-(2-bromopropionyl)phenyl)acetamide; In tetrahydrofuran; at 20 ℃; for 5h; Further stages.;

Reference yield: 80.0%

N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide (81112-08-5) + diethyl malonate (105-53-3) → 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester (81937-39-5)

Guidance literature:

diethyl malonate; With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 1.5h;

N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

With water; In N,N-dimethyl-formamide;

Reference yield:

Acetanilid (103-84-4) → 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester (81937-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: carbon disulfide; aluminum (III) chloride / 50 °C

2.1: bromine / chloroform

2.2: 24 h / 20 °C / pH 8

3.1: sodium ethanolate / ethanol / Cooling with ice

3.2: 8.17 h / 35 - 75 °C

With carbon disulfide; aluminum (III) chloride; bromine; sodium ethanolate; In ethanol; chloroform; 1.1: Friedel-Crafts reaction;

DOI:10.1007/s00044-010-9319-0

upstream raw materials:

N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide

diethyl malonate

N-(4-(2-bromopropionyl)phenyl)acetamide

Acetanilid

Downstream raw materials:

C₁₈H₁₆N₄O₃

C₁₈H₁₆N₄O₃

C₁₈H₁₇N₃O₃

C₁₈H₁₇N₃O₂

Refernces

• 1、 Wang, Lisheng,Zhou, Hongxiang,Yang, Bin,Chen, Zhigang,Yang, Hua. "Synthesis and anti-congestive heart failure activity of novel levosimendan analogues". experimental part. p. 287 - 292. Retrieved 2012/06/05.
• 2、 Wang, Teng,Dong, Ying,Wang, Li-Chen,Chen, Zhen. "Synthesis and bioactivity of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives". . p. 641 - 646. Retrieved 2008/03/11.