Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 1,1-dimethylethyl ester
• CAS No.: 158851-29-7
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• DSSTox Substance ID: DTXSID20462686
• Nikkaji Number: J1.811.828I
• Wikidata: Q82287257
• Mol file: 158851-29-7.mol

Synonyms:158851-29-7;Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 1,1-dimethylethyl ester;DTXSID20462686

Chemical Property of Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 1,1-dimethylethyl ester

Chemical Property:

• PSA: 41.82000
• LogP: 3.64280
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C=C)C1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C=C)C1=CC=CC=C1

Technology Process of Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 1,1-dimethylethyl ester

There total 14 articles about Carbamic acid, [(1R)-1-phenyl-2-propenyl]-, 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R)-1-phenylprop-2-en-1-amine (325490-29-7) → (+)-tert-butyl [(1R)-1-phenylprop-2-en-1-yl]imidocarbonate (158851-29-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane;

DOI:10.1016/S0040-4039(02)01832-4

Reference yield: 93.0%

(+)-tert-butyl formyl[(1R)-1-phenylprop-2-en-1-yl]carbamate (1234693-00-5) → (+)-tert-butyl [(1R)-1-phenylprop-2-en-1-yl]imidocarbonate (158851-29-7)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 1.5h;

DOI:10.1002/chem.201100649

Reference yield: 92.0%

C15H21NO3 (1315566-29-0) → (+)-tert-butyl [(1R)-1-phenylprop-2-en-1-yl]imidocarbonate (158851-29-7)

Guidance literature:

With samarium diiodide; 1,2-Diiodoethane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0030-1261187

upstream raw materials:

di-tert-butyl dicarbonate

(1R)-1-phenylprop-2-en-1-amine

benzaldehyde

benzaldehyde (E)-O-[(1S)-2-hydroxy-1-phenylethyl]oxime

Downstream raw materials:

(2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde

tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-4-pentenylcarbamate

tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-1-phenylpentenylcarbamate

(+)-methyl (2E,6R)-6-[(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Refernces

• 1、 Zheng, Bao-Hui,Ding, Chang-Hua,Hou, Xue-Long. "Regio- and enantioselective Pd-catalyzed allylic amination of monosubsti-tuted allylic substrates with BocNHOMe". . p. 2262 - 2264. Retrieved 2011/10/19.
• 2、 Lindsley, Stacey R.,Moore, Keith P.,Rajapakse, Hemaka A.,Selnick, Harold G.,Young, Mary Beth,Zhu, Hong,Munshi, Sanjeev,Kuo, Lawrence,McGaughey, Georgia B.,Colussi, Dennis,Crouthamel, Ming-Chih,Lai, Ming-Tain,Pietrak, Beth,Price, Eric A.,Sankaranarayanan, Sethu,Simon, Adam J.,Seabrook, Guy R.,Hazuda, Daria J.,Pudvah, Nicole T.,Hochman, Jerome H.,Graham, Samuel L.,Vacca, Joseph P.,Nantermet, Philippe G.. "Design, synthesis, and SAR of macrocyclic tertiary carbinamine BACE-1 inhibitors". . p. 4057 - 4061. Retrieved 2008/02/10.