methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate

Base Information

• Chemical Name: methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate
• CAS No.: 362703-30-8
• Molecular Formula: C8H11NO3
• Molecular Weight: 169.18
• Hs Code.: 2932999099
• European Community (EC) Number: 850-150-3
• DSSTox Substance ID: DTXSID80587389
• Wikidata: Q82479797
• Mol file: 362703-30-8.mol

Synonyms:methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate;362703-30-8;methyl 4-cyanooxane-4-carboxylate;SCHEMBL1192865;DTXSID80587389;ZOCVBMSJKWEGQO-UHFFFAOYSA-N;MFCD11100237;AKOS005072631;GC-0734;MCULE-9795186838;DB-343376;methyl 4-cyanotetrahydropyran-4-carboxylate;CS-0008710;EN300-58901;methyl4-cyanotetrahydro-2H-pyran-4-carboxylate;A913661;J-522340;Z825761102

Chemical Property of methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate

Chemical Property:

• PSA: 59.32000
• LogP: 0.47978
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 169.07389321
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

methyl4-cyanotetrahydro-2H-pyran-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CCOCC1)C#N

Technology Process of methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate

There total 2 articles about methyl 4-cyanotetrahydro-2H-pyran-4-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: 62.8%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + methyl 2-cyanoacetate (105-34-0) → methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (362703-30-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 85 ℃; for 3h;

DOI:10.1016/j.ejmech.2018.09.025

Reference yield:

3-oxa-1,5-dichloropentane (111-44-4) + methyl 2-cyanoacetate (105-34-0) → methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (362703-30-8)

Guidance literature:

methyl 2-cyanoacetate; With sodium t-butanolate; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 3h;

3-oxa-1,5-dichloropentane; In N,N-dimethyl-formamide; at 85 ℃; for 20h;

Reference yield: 84.0%

methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (362703-30-8) + 4-cyanotetrahydro-2H-pyran-4-carboxylic acid (848821-06-7) → tetrahydro-2H-pyran-4-carboxylic acid (5337-03-1)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 9h; Product distribution / selectivity;

upstream raw materials:

1,1'-oxybis(2-bromo-ethane)

methyl 2-cyanoacetate

3-oxa-1,5-dichloropentane

Downstream raw materials:

4-{[4-(2-methyl-quinolin-4-ylmethoxy)-benzoylamino]-methyl}-tetrahydro-pyran-4-carboxylic acid methyl ester

tetrahydro-2H-pyran-4-carboxylic acid

4-(hydroxymethyl)-tetrahydro-2H-pyran-4-carbonitrile

2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)methyl)piperazin-1-yl)-N-((3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide