5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester

Base Information

• Chemical Name: 5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester
• CAS No.: 50899-14-4
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• DSSTox Substance ID: DTXSID70482652
• Nikkaji Number: J843.867F
• Mol file: 50899-14-4.mol

Synonyms:50899-14-4;5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester;SCHEMBL24518312;DTXSID70482652;AKOS017417015;Ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate;(+)-ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate

Chemical Property of 5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(=NO1)C2=CC=CC=C2

Technology Process of 5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester

There total 23 articles about 5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, ethyl ester 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: 94.0%

ethyl acrylate (140-88-5,9003-32-1) + Benzaldoxime (932-90-1) → (+/-)-ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate (50899-14-4)

Guidance literature:

Benzaldoxime; With N-chloro-succinimide; C₆₄H₁₁₆O₂₀; In water; at 20 ℃; for 4h;

ethyl acrylate; With triethylamine; In water; at 20 ℃; for 8h;

Reference yield: 94.0%

benzohydroximoyl chloride (698-16-8) + ethyl acrylate (140-88-5,9003-32-1) → (+/-)-ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate (50899-14-4)

Guidance literature:

In d⁽⁴⁾-methanol; at 20 ℃; for 5h; Solvent; Reagent/catalyst; Time; Reactivity; Molecular sieve;

DOI:10.1016/j.tetlet.2009.02.178

Reference yield: 93.0%

benzaldehyde (100-52-7) + ethyl acrylate (140-88-5,9003-32-1) → (+/-)-ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate (50899-14-4)

Guidance literature:

benzaldehyde; With toluene-4-sulfonic acid hydrazide; In methanol; at 60 ℃; for 0.5h;

ethyl acrylate; With tert.-butylnitrite; N,N,N,N,-tetramethylethylenediamine; copper dichloride; In tetrahydrofuran; at 65 ℃; for 24h; Sealed tube;

upstream raw materials:

ethyl acrylate

Benzaldoxime

(S)-3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid

ethanol

Downstream raw materials:

(R)-3-phenyl-Δ²-isoxazoline-5-methanol

(S)-5-(Hydroxymethyl)-Δ²-isoxazoline

(S)-3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid

(R)-3-Phenyl-4,5-dihydro-isoxazole-5-carboxylic acid

Refernces

• 1、 -. "Aqueous phase preparation method of isoxazoline compound participating in vitamin E micro-micelle". Paragraph 0086-0088. . Retrieved 2021/11/21.
• 2、 Bao, Xiaoguang,Cheng, Xionglve,Jiang, Gangzhong,Jin, Feng,Li, Xingxing,Ma, Liang,Tao, Suyan,Wan, Xiaobing,Yang, Jinwei. "[2 + 2 + 1] Cycloaddition ofN-tosylhydrazones,tert-butyl nitrite and alkenes: a general and practical access to isoxazolines". . p. 9823 - 9830. Retrieved 2021/07/28.