1-(Diphenylmethyl)-3-azetidinyl methanesulfonate

Base Information

• Chemical Name: 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate
• CAS No.: 33301-41-6
• Molecular Formula: C17H19NO3S
• Molecular Weight: 317.409
• Hs Code.: 29339900
• European Community (EC) Number: 608-857-8,922-632-4
• DSSTox Substance ID: DTXSID20374452
• Nikkaji Number: J2.350.111B
• Wikidata: Q72473319
• ChEMBL ID: CHEMBL3676399
• Mol file: 33301-41-6.mol

Synonyms:3-Azetidinol,1-(diphenylmethyl)-, methanesulfonate (ester) (8CI,9CI);1-(Diphenylmethyl)-3-(mesyloxy)azetidine;1-(Diphenylmethyl)-3-[(methylsulfonyl)oxy]azetidine;1-Benzhydryl-3-[(methylsulfonyl)oxy]azetidine;1-Benzhydryl-3-azetidinylmethanesulfonate;1-Benzhydryl-3-mesyloxyazetidine;1-Benzhydryl-3-methanesulfonyloxyazetidine;3-(Mesyloxy)-N-(diphenylmethyl)azetidine;3-[(Methylsulfonyl)oxy]-1-benzhydrylazetidine;Methanesulfonic acid1-benzhydrylazetidin-3-yl ester;

Chemical Property of 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1.22E-08mmHg at 25°C
• Melting Point: 111-112 °C
• Refractive Index: 1.622
• Boiling Point: 459.9 °C at 760 mmHg
• PKA: 5.67±0.10(Predicted)
• Flash Point: 231.9 °C
• PSA: 54.99000
• Density: 1.28 g/cm³
• LogP: 3.45510
• Storage Temp.: Room temperature.
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 317.10856464
• Heavy Atom Count: 22
• Complexity: 423

Purity/Quality:

99.0% ^*data from raw suppliers

1-Benzhydryl-3-methanesulfonatoazetidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OC1CN(C1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: A proline analog and proline formation inhibitor

Technology Process of 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate

There total 9 articles about 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate 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: 100.0%

1-(diphenylmethyl)-3-hydroxyazetidine (18621-17-5) + methanesulfonyl chloride (124-63-0) → 1-benzhydryl-3-azetidinyl methanesulfonate (33301-41-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

Reference yield: 95.0%

→ 1-benzhydryl-3-azetidinyl methanesulfonate (33301-41-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 4h;

Reference yield: 91.0%

methanesulfonyl chloride (124-63-0) + 1-(diphenylmethyl)-3-azetidinol hydrochloride (90604-02-7) → 1-benzhydryl-3-azetidinyl methanesulfonate (33301-41-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Product distribution / selectivity;

upstream raw materials:

1-(diphenylmethyl)-3-hydroxyazetidine

methanesulfonyl chloride

Benzhydrylamine

3-(dimethylamino)azetidine dihydrochloride

Downstream raw materials:

diethyl (1-benzhydrylazetidin-3-yl)phosphonate

1-(1,1-diphenylmethyl)azetidine-3-carbonitrile

2-(1-benzhydrylazetidin-3-yl)isoindoline-1,3-dione

1-Benzhydryl-3-(diethoxymethyl-O-ethylphosphinyl)azetidine

Refernces

• 1、 Li, Bryan,Witt, Michael F.,Brandt, Thomas A.,Whritenour, David. "An efficient two-step synthesis of 3-amino-1-benzhydrylazetidine". . p. 478 - 480. Retrieved 2006.
• 2、 -. "NEW TRIAZOLYL DERIVATIVES AS GABA A ALPHA5 PAM". Page/Page column 73. . Retrieved 2021/11/20.
• 3、 Roagna, Giulia,Ascough, David M. H.,Ibba, Francesco,Vicini, Anna Chiara,Fontana, Alberto,Christensen, Kirsten E.,Peschiulli, Aldo,Oehlrich, Daniel,Misale, Antonio,Trabanco, Andrés A.,Paton, Robert S.,Pupo, Gabriele,Gouverneur, Véronique. "Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines". supporting information. p. 14045 - 14051. Retrieved 2020/09/16.