(R)-(-)-N-Benzyl-2-phenylglycinol

Base Information

• Chemical Name: (R)-(-)-N-Benzyl-2-phenylglycinol
• CAS No.: 14231-57-3
• Molecular Formula: C15H17 N O
• Molecular Weight: 227.306
• Hs Code.: 2922199090
• European Community (EC) Number: 624-935-4
• DSSTox Substance ID: DTXSID60443111
• Nikkaji Number: J996.884I
• Wikidata: Q76415882
• Mol file: 14231-57-3.mol

Synonyms:(R)-(-)-N-Benzyl-2-phenylglycinol;14231-57-3;(R)-2-(Benzylamino)-2-phenylethanol;(2R)-2-(BENZYLAMINO)-2-PHENYLETHANOL;(R)-(?)-N-Benzyl-2-phenylglycinol;SCHEMBL424037;DTXSID60443111;(R)-()-N-Benzyl-2-phenylglycinol;(R)-beta-(Benzylamino)benzeneethanol;AKOS015888852;HY-W141895;BP-12910;BS-22578;(2R)-2-(benzylamino)-2-phenylethan-1-ol;(R)-(-)-N-Benzyl-2-phenylglycinol, 98%;CS-0201689;E82408;J-007636

Chemical Property of (R)-(-)-N-Benzyl-2-phenylglycinol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• Boiling Point: 386.4°Cat760mmHg
• Flash Point: 136.9°C
• PSA: 32.26000
• Density: 1.1g/cm³
• LogP: 2.90070
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 227.131014166
• Heavy Atom Count: 17
• Complexity: 195

Purity/Quality:

99.90% ^*data from raw suppliers

(R)-(-)-N-Benzyl-2-phenylglycinol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(CO)C2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)CN[C@@H](CO)C2=CC=CC=C2
• Uses: Used for the asymmetric synthesis of α-amino phosphonic acids. Starting material for a practical route to optically pure β-substituted amines.

Technology Process of (R)-(-)-N-Benzyl-2-phenylglycinol

There total 45 articles about (R)-(-)-N-Benzyl-2-phenylglycinol 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: 93.0%

allyl bromide (106-95-6) + (R)-2-Phenyl-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethanol → (R)-N-benzyl-2-phenylglycinol (14231-57-3) + (2R)-2-phenyl-2-[(1'R)-1'-phenylbut-3'-enylamino]ethanol (132313-03-2)

Guidance literature:

(R)-2-Phenyl-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethanol; samarium; trimethylaluminum; In hexane; at 0 ℃;

allyl bromide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo0014616

Reference yield: 85.0%

D-2-phenylglycinol (56613-80-0) + benzaldehyde (100-52-7) → (R)-N-benzyl-2-phenylglycinol (14231-57-3)

Guidance literature:

D-2-phenylglycinol; benzaldehyde; In methanol; at 20 ℃; for 8h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

DOI:10.1021/acs.joc.8b03244

Reference yield: 85.0%

(R)-2-Phenyl-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethanol → (R)-N-benzyl-2-phenylglycinol (14231-57-3) + (S,R)-1,2-diphenyl-N,N'-bis((R)-1-(hydroxymethyl)-2-phenylmethyl)ethylenediamine + (S,S)-1,2-diphenyl-N,N'-bis((R)-1-(hydroxymethyl)-2-phenylmethyl)ethylenediamine

Guidance literature:

(R)-2-Phenyl-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethanol; samarium; trimethylaluminum; In hexane; at 0 ℃;

With iodine; In tetrahydrofuran; at 0 ℃; for 1h; Further stages.;

DOI:10.1021/jo0014616

upstream raw materials:

D-2-phenylglycinol

benzyl bromide

Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester

N-benzoyl-α-phenylglycine

Downstream raw materials:

(2R,4R)-3-Benzyl-2-butyl-4-phenyl-oxazolidine

(1R,1'R)-N-benzyl-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine

(1S,1'R)-N-benzyl-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine

(2S,4R)-N-benzyl-2-methyl-4-phenyl-1,3-oxazolidine

Refernces

• 1、 Zhang, Yazhen,Huang, Liliang,Li, Xiaoyang,Wang, Le,Feng, Huangdi. "Chemo- and Diastereoselective Synthesis of N-Propargyl Oxazolidines through a Copper-Catalyzed Domino A3 Reaction". supporting information. p. 5046 - 5055. Retrieved 2019/05/10.
• 2、 Arigala, Pitchaiah,Sadu, Venkata S.,Hwang, In-Taek,Hwang, Jin-Soo,Kim, Chul-Ung,Lee, Kee-In. "Copper-Catalyzed Regio- and Stereoselective Ring-Opening of Cyclic Sulfamidates with Grignard Reagents assisted by Lithium Chloride". supporting information. p. 2027 - 2032. Retrieved 2015/06/23.