Beta-oxo-2-naphthalenepropanoic acid

Base Information

• Chemical Name: Beta-oxo-2-naphthalenepropanoic acid
• CAS No.: 824424-57-9
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.221
• DSSTox Substance ID: DTXSID60431073
• Nikkaji Number: J3.065.173A
• Wikidata: Q82244868
• Mol file: 824424-57-9.mol

Synonyms:Beta-oxo-2-naphthalenepropanoic acid;824424-57-9;SCHEMBL3373461;DTXSID60431073;3-Oxo-3-(2-naphthyl)propanoic acid;3-naphthalen-2-yl-3-oxopropanoic acid;FT-0738374

Chemical Property of Beta-oxo-2-naphthalenepropanoic acid

Chemical Property:

• PSA: 54.37000
• LogP: 2.49720
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.062994177
• Heavy Atom Count: 16
• Complexity: 285

Purity/Quality:

98% ^*data from raw suppliers

BETA-OXO-2-NAPHTHALENEPROPANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)C(=O)CC(=O)O

Technology Process of Beta-oxo-2-naphthalenepropanoic acid

There total 2 articles about Beta-oxo-2-naphthalenepropanoic acid 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:

methyl 3-naphthalen-2-yl-3-oxopropanoate (158053-33-9) → 3-(naphthalen-2-yl)-3-oxopropanoic acid (824424-57-9)

Guidance literature:

With sodium hydroxide; at 20 ℃;

DOI:10.1021/ol7019394

Reference yield:

methyl 2-naphthyl ketone (93-08-3) → 3-(naphthalen-2-yl)-3-oxopropanoic acid (824424-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

1.2: Reflux; Inert atmosphere

2.1: sodium hydroxide / 12 h

With sodium hydride; sodium hydroxide; In 1,4-dioxane;

DOI:10.1002/cjoc.201700271

Reference yield: 95.0%

3-(naphthalen-2-yl)-3-oxopropanoic acid (824424-57-9) + 1′-benzyl-3′-hydroxy-1′,3′-dihydro-1H,2′H-3,3′-biindol-2′-one (676612-41-2) → (R)-1-benzyl-3-(1H-indol-3-yl)-3-(2-(naphthalen-2-yl)-2-oxoethyl)indolin-2-one

Guidance literature:

With C₄₈H₂₅F₁₂O₄P; sodium sulfate; In dichloromethane; at -35 ℃; enantioselective reaction;

DOI:10.1021/acs.orglett.5b00159

upstream raw materials:

methyl 3-naphthalen-2-yl-3-oxopropanoate

methyl 2-naphthyl ketone

Refernces

• 1、 Chen, Li-Jun,Li, Wei,Shen, Bao-Chun,Sun, Zhong-Wen,Xie, Hui-Ding,Zhang, Cong-Cong. "Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines". supporting information. p. 8607 - 8612. Retrieved 2021/10/20.
• 2、 He, Hu,Zheng, Xiao-Jian,Li, Yi,Dai, Li-Xin,You, Shu-Li. "Ir-catalyzed regio- and enantioselective decarboxylative allylic alkylations". . p. 4339 - 4341. Retrieved 2008/03/12.