L-(7-hydroxycoumarin-4-yl) ethylglycine

Base Information

• Chemical Name: L-(7-hydroxycoumarin-4-yl) ethylglycine
• CAS No.: 905442-42-4
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID70705338
• Wikidata: Q82638177
• Mol file: 905442-42-4.mol

Synonyms:(7-hydroxycoumarin-4-yl) ethylglycine;L-(7-hydroxycoumarin-4-yl) ethylglycine

Chemical Property of L-(7-hydroxycoumarin-4-yl) ethylglycine

Chemical Property:

• Melting Point: 276-281 °C
• Boiling Point: 563.8±50.0 °C(Predicted)
• PKA: 2.28±0.10(Predicted)
• PSA: 113.76000
• Density: 1.440±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 1.54340
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 263.07937252
• Heavy Atom Count: 19
• Complexity: 406

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-2-Amino-4-(7-hydroxy-2-oxo-2H-chromen-4-yl)butanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)OC(=O)C=C2CCC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C=C1O)OC(=O)C=C2CC[C@H](C(=O)O)N
• Uses: The courmarin-based unnatural amino acid is an effective fluorophore; which has been incoporated into several studies of protein interactions.

Technology Process of L-(7-hydroxycoumarin-4-yl) ethylglycine

There total 5 articles about L-(7-hydroxycoumarin-4-yl) ethylglycine 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: 64.0%

recorcinol (108-46-3) + (2S)-2-benzyloxycarbonylamino-5-oxo-heptanedioic acid 1-benzyl ester 6-ethyl ester (608535-19-9) → L-2-((7-hydroxycoumarin-4-yl)-ethane-2-yl)glycine (905442-42-4)

Guidance literature:

With methanesulfonic acid; at 20 ℃; for 4h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.bmc.2012.10.055

Reference yield: 60.0%

(Z)-(2S)-2-benzyloxycarbonylamino-5-(2,4-dimethoxyphenyl)-5-heptenedioic acid 1-benzyl 7-ethyl ester → L-2-((7-hydroxycoumarin-4-yl)-ethane-2-yl)glycine (905442-42-4)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/acs.orglett.7b00854

Reference yield: 38.0%

C25H27NO9 + recorcinol (108-46-3) → L-2-((7-hydroxycoumarin-4-yl)-ethane-2-yl)glycine (905442-42-4)

Guidance literature:

With methanesulfonic acid; at 20 ℃; for 1h;

DOI:10.1021/ja106416g

upstream raw materials:

recorcinol

(2S)-2-benzyloxycarbonylamino-5-oxo-heptanedioic acid 1-benzyl ester 6-ethyl ester

Cbz-(L)-Glu-OBn

Refernces

• 1、 Amaro, Mariana,Brezovsky, Jan,Ková?ová, Silvia,Sykora, Jan,Bedná?, David,Němec, Václav,Li?ková, Veronika,Kurumbang, Nagendra Prasad,Beerens, Koen,Chaloupková, Radka,Paruch, Kamil,Hof, Martin,Damborsky, Ji?í. "Site-specific analysis of protein hydration based on unnatural amino acid fluorescence". supporting information. p. 4988 - 4992. Retrieved 2015/05/05.
• 2、 Koopmans, Timo,Van Haren, Matthijs,Van Ufford, Linda Quarles,Beekman, Jeffrey M.,Martin, Nathaniel I.. "A concise preparation of the fluorescent amino acid L-(7-hydroxycoumarin-4- yl) ethylglycine and extension of its utility in solid phase peptide synthesis". . p. 553 - 559. Retrieved 2013/02/25.