Ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate

Base Information

• Chemical Name: Ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate
• CAS No.: 1013-14-5
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Hs Code.: 2934999090
• NSC Number: 134330
• DSSTox Substance ID: DTXSID90300021
• Wikidata: Q82042778
• Mol file: 1013-14-5.mol

Synonyms:1013-14-5;ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate;Ethyl 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate;ethyl 4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxylate;4,5,6,7-Hexahydrobenzo[d]isoxazole-3-carboxylic acid ethyl ester;NSC134330;SCHEMBL13151524;DTXSID90300021;4,5,6,7-Hexahydro-benzo[d]isoxazole-3-carboxylicacidethylester;BAA01314;MFCD08701222;STL069524;AKOS003673904;NSC-134330;CS-0316753;H10962;AN-329/43449474;ethyl-4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate;Ethyl4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate

Chemical Property of Ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate

Chemical Property:

• Vapor Pressure: 3.82E-05mmHg at 25°C
• Boiling Point: 352.5°C at 760 mmHg
• Flash Point: 167°C
• PSA: 52.33000
• Density: 1.171g/cm³
• LogP: 1.73010
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NOC2=C1CCCC2

Technology Process of Ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate

There total 5 articles about Ethyl 4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxylate 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: 70.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + oxalic acid diethyl ester (95-92-1) → ethyl 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate (1013-14-5)

Guidance literature:

cyclohexanone; oxalic acid diethyl ester; With sodium ethanolate; In ethanol; at 20 ℃; for 20h;

With hydroxylamine hydrochloride; acetic acid; In ethanol; water; for 20h;

With toluene-4-sulfonic acid; In ethanol; for 2h; Reflux;

DOI:10.1134/S1070428011080136

Reference yield: 25.0%

1-(Trimethylsilyloxy)cyclohexene (6651-36-1) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → ethyl 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate (1013-14-5) + diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide (18417-40-8)

Guidance literature:

1-(Trimethylsilyloxy)cyclohexene; ethyl 2-chloro-2-(hydroxyimino)acetate; With triethylamine; In hexane; at 20 ℃; Inert atmosphere;

With toluene-4-sulfonic acid; In hexane; at 70 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol202002r

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → ethyl 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate (1013-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride

2: hydroxylamine

With hydroxylamine; sodium hydride;

upstream raw materials:

1-(Trimethylsilyloxy)cyclohexene

ethyl 2-chloro-2-(hydroxyimino)acetate

cyclohexanone

oxalic acid diethyl ester

Refernces

• 1、 Schmitt, Daniel C.,Lam, Leighann,Johnson, Jeffrey S.. "Three-component coupling approach to trachyspic acid". supporting information; experimental part. p. 5136 - 5139. Retrieved 2011/11/29.