Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester
• CAS No.: 5176-28-3
• Molecular Formula: C15H17NO2
• Molecular Weight: 243.305
• Hs Code.: 2925290090
• European Community (EC) Number: 696-499-3
• DSSTox Substance ID: DTXSID30503559
• Nikkaji Number: J2.281.781G
• Mol file: 5176-28-3.mol

Synonyms:5176-28-3;Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester;7-tert-Butoxycarbonyl-2,3-benzo-7-azabicyclo[2.2.1]hepta-2,5-diene;tert-Butyl 1,4-dihydro-1,4-epiminonaphthalene-9-carboxylate;tert-butyl 11-azatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-11-carboxylate;tert-Butyl 11-azatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-11-carboxylate;tert-butyl 11-azatricyclo[6.2.1.0?,?]undeca-2,4,6,9-tetraene-11-carboxylate;SCHEMBL13137750;DTXSID30503559;CS-M1955;MFCD22573547;AKOS015996887;SS-4455;C12351;tert-Butyl 11-azatricyclo[6.2.1.0 {2,7}]undeca- 2,4,6,9-tetraene-11-carboxylate;tert-Butyl 11-azatricyclo[6.2.1.0^{2,7}]-undeca- 2,4,6,9-tetraene-11-carboxylate;tert-Butyl 11-azatricyclo[6.2.1.0^{2,7}]-undeca-2,4,6,9-tetraene-11-carboxylate;tert-butyl 11-azatricyclo[6.2.1.0^{2,7}]undeca- 2,4,6,9-tetraene-11-carboxylate

Chemical Property of Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester

Chemical Property:

• Melting Point: 67-70 °C
• Boiling Point: 342.1±42.0 °C(Predicted)
• PKA: -1.88±0.20(Predicted)
• PSA: 29.54000
• Density: 1.177±0.06 g/cm3(Predicted)
• LogP: 3.52720
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 243.125928785
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

NLT 98% ^*data from raw suppliers

tert-Butyl 11-azatricyclo[6.2.1.0{2,7}]-undeca- 2,4,6,9-tetraene-11-carboxylate >97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2C=CC1C3=CC=CC=C23

Technology Process of Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl ester

There total 13 articles about Naphthalen-1,4-imine-9-carboxylic acid, 1,4-dihydro-, 1,1-dimethylethyl 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: 81.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + 2-hydroxyphenyl boronic acid (89466-08-0) → N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene (5176-28-3)

Guidance literature:

2-hydroxyphenyl boronic acid; With 2,2-Dimethyl-1,3-propanediol; In dichloromethane; at 20 ℃; for 3h; Schlenk technique; Inert atmosphere;

With toluene; Inert atmosphere;

N-tert-butyloxycarbonyl-pyrrole; With Nonafluorobutanesulfonyl fluoride; sodium hydride; caesium carbonate; In tetrahydrofuran; paraffin oil; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.9b03169

Reference yield: 79.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene (5176-28-3)

Guidance literature:

With isopentyl nitrite; In 1,2-dimethoxyethane; at 50 ℃;

DOI:10.1021/ol0478133

Reference yield: 66.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → N-Boc-7-azabenzobicyclo[2.2.1]heptadiene (5176-28-3)

Guidance literature:

With isopentyl nitrite; In 1,2-dimethoxyethane; at 50 ℃; for 1.25h;

DOI:10.1021/ol801768e

upstream raw materials:

o-fluorobromobenzene

N-tert-butyloxycarbonyl-pyrrole

anthranilic acid

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Downstream raw materials:

C₃₃H₃₁NO₂

C₂₂H₂₁N₃O₅

1,4-dihydro-1,4-epiazano-naphthalene

(1R,2R)-[2-(allyl(phenyl)amino)-1,2-dihydronaphthalen-1-yl]-carbamic acid tert-butyl ester

Refernces

• 1、 Gómez Arrayás, Ramón,Cabrera, Silvia,Carretero, Juan C.. "Copper-catalyzed anti-stereocontrolled ring-opening of azabicyclic alkenes with Grignard reagents". . p. 219 - 221. Retrieved 2005.
• 2、 Pandey, Ganesh,Varkhedkar, Rajesh,Tiwari, Divya. "Efficient access to enantiopure 1,3-disubstituted isoindolines from selective catalytic fragmentation of an original desymmetrized rigid overbred template". . p. 4438 - 4448. Retrieved 2015.
• 3、 -. "COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS". Paragraph 0253-0254. . Retrieved 2021/07/10.
• 4、 Devaraj, Karthik,Ingner, Fredric J.L.,Sollert, Carina,Gates, Paul J.,Orthaber, Andreas,Pilarski, Lukasz T.. "Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation". . p. 5863 - 5871. Retrieved 2019/04/16.