Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl ester

Base Information

• Chemical Name: Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl ester
• CAS No.: 218601-55-9
• Molecular Formula: C16H25NO2
• Molecular Weight: 263.38
• DSSTox Substance ID: DTXSID70440833
• Nikkaji Number: J1.157.498J
• Wikidata: Q82257264
• Mol file: 218601-55-9.mol

Synonyms:218601-55-9;Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl ester;DTXSID70440833;Diisopropylcarbamic acid 3-phenylpropyl ester

Chemical Property of Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl ester

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)C(=O)OCCCC1=CC=CC=C1

Technology Process of Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl ester

There total 1 articles about Carbamic acid, bis(1-methylethyl)-, 3-phenylpropyl 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: 92.0%

N,N-diisopropylcarbamoyl chloride (19009-39-3) + 3-Phenyl-1-propanol (122-97-4) → 3-phenylpropyl N,N-diisopropylcarbamate (218601-55-9)

Guidance literature:

With triethylamine; In dichloromethane; for 16h; Reflux;

DOI:10.1002/anie.201711390

Reference yield: 91.0%

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 3-phenylpropyl N,N-diisopropylcarbamate (218601-55-9) → (R)-2-(1,3-diphenylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-73-8)

Guidance literature:

3-phenylpropyl N,N-diisopropylcarbamate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; at -78 ℃; for 5h; Inert atmosphere;

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; In diethyl ether; Inert atmosphere;

With magnesium bromide; In diethyl ether; at -78 ℃; enantioselective reaction; Reflux; Inert atmosphere;

DOI:10.1002/anie.200901900

Reference yield: 90.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 3-phenylpropyl N,N-diisopropylcarbamate (218601-55-9) → N,N-diisopropyl O-[(S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]prop-1-yl carbamate (821784-98-9)

Guidance literature:

3-phenylpropyl N,N-diisopropylcarbamate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; cyclohexane; at -78 ℃; for 5.25h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In diethyl ether; cyclohexane; at -78 ℃; for 1.25h; Inert atmosphere;

DOI:10.1002/anie.201606641

upstream raw materials:

N,N-diisopropylcarbamoyl chloride

3-Phenyl-1-propanol

Downstream raw materials:

1,6-diphenylhex-3-ene

N,N-diisopropyl O-[(S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]prop-1-yl carbamate

C₁₇H₂₅NO₄

(S)-4-phenyl-1,2-butanediol

Refernces

• 1、 Gerleve, Carolin,Kischkewitz, Marvin,Studer, Armido. "Synthesis of α-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes". supporting information. p. 2441 - 2444. Retrieved 2018/01/27.
• 2、 Wu, Zhenhua,Sun, Xun,Potter, Kristin,Cao, Yang,Zakharov, Lev N.,Blakemore, Paul R.. "Stereospecific Synthesis of Alkenes by Eliminative Cross-Coupling of Enantioenriched sp3-Hybridized Carbenoids". . p. 12285 - 12289. Retrieved 2016/10/13.