5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Base Information

• Chemical Name: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
• CAS No.: 1219-33-6
• Molecular Formula: C13H10O5
• Molecular Weight: 246.219
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID70424299
• Wikidata: Q72442588
• ChEMBL ID: CHEMBL487332
• Mol file: 1219-33-6.mol

Synonyms:5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid;1219-33-6;4-oxo-5-phenylmethoxypyran-2-carboxylic acid;4H-Pyran-2-carboxylic acid, 4-oxo-5-(phenylmethoxy)-;5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid;5-benzyloxy-4-pyrone-2-carboxylic acid;5-benzyloxy-4-pyrone-2-carboxylicacid;CHEMBL487332;SCHEMBL1037140;DTXSID70424299;RGZZNPNSZZJJSH-UHFFFAOYSA-N;BBL034968;MFCD08531038;STL426079;AKOS005207616;5-benzyloxy-4-oxo-pyran-2-carboxylic acid;CS-0037813;FT-0651228;EN300-100426;5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylicacid;5-(Benzyloxy)-4-oxo-4H~pyran-2-carboxylic acid;5~(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid;A847985;A891285;J-516759;F2158-0173;Z1336492464;4-OXO-5-(PHENYLMETHOXY)-4H-PYRAN-2-CARBOXYLIC ACID

Chemical Property of 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Chemical Property:

• Melting Point: 196-198℃ (methanol )
• Boiling Point: 501.5±50.0 °C(Predicted)
• PKA: 1.67±0.20(Predicted)
• PSA: 76.74000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 1.91700
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 246.05282342
• Heavy Atom Count: 18
• Complexity: 402

Purity/Quality:

98%min ^*data from raw suppliers

5-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=COC(=CC2=O)C(=O)O

Technology Process of 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

There total 12 articles about 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic 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: 91.0%

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one (15771-06-9) → 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (1219-33-6)

Guidance literature:

With jones' reagent; In acetone; Ambient temperature;

Reference yield: 38.0%

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one (15771-06-9) → 5-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde (18234-41-8) + 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (1219-33-6)

Guidance literature:

With potassium bromate; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; sodium hydrogencarbonate; In dichloromethane; water; at 0 ℃; for 0.1 - 0.15h; Product distribution / selectivity;

Reference yield:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) + benzyl bromide (100-39-0) → 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (1219-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 70 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / water; dichloromethane / 2 h / 0 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate; caesium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/00304948.2018.1525990

upstream raw materials:

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

benzyl chloride

benzyl bromide

Downstream raw materials:

3-Benzyloxy-4-pyrone

3-hydroxy-pyran-4-one

1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid

7-(Benzyloxy)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione

Refernces

• 1、 Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao. "Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity". . . Retrieved 2020/05/22.
• 2、 Xie, Yuan-Yuan,Lu, Zidong,Kong, Xiao-Le,Zhou, Tao,Bansal, Sukhi,Hider, Robert. "Systematic comparison of the mono-, dimethyl-and trimethyl 3-hydroxy-4(1H)-pyridones-Attempted optimization of the orally active iron chelator, deferiprone". . p. 132 - 140. Retrieved 2016/04/05.