Dipivefrine hydrochloride, (R)-

Base Information

• Chemical Name: Dipivefrine hydrochloride, (R)-
• CAS No.: 79071-01-5
• Molecular Formula: C₁₉H₂₉NO₅*ClH
• Molecular Weight: 387.904
• UNII: 6107X69460
• Mol file: 79071-01-5.mol

Synonyms:(+)-dipivefrin;(-)-dipivefrin;(R)-dipivefrine;(RS)-4-(1-hydroxy-2-(methylamino)ethyl)-O-phenylene dipivalate hydrochloride;(S)-dipivefrin;(S)-dipivefrine;adrenaline dipivalate;Akpro;Apo-Dipivefrin;d Epifrin;Diopine;dipivaloylepinephrine;dipivalyl epinephrine;dipivefrin;dipivefrin acetate, (+-)-isomer;dipivefrin citrate (1:1), (+-)-isomer;dipivefrin HCl;dipivefrin hydrochloride;dipivefrin hydrochloride, (+-)-isomer;dipivefrin hydrochloride, (R)-;dipivefrin hydrochloride, (S)-;dipivefrin monophosphate, (+-)-isomer;dipivefrin monosulfate, (+-)-isomer;dipivefrin nitrate, (+-)-isomer;dipivefrin perchlorate;dipivefrin propanoate, (+-)-isomer;dipivefrin tartrate (1:1), (+-)-(R-(R*,R*))-isomer;dipivefrin tartrate (1:1), (R)-(R-(R*,R*))-isomer;dipivefrin, (R)-isomer;dipivefrine;dipivefrine hydrochloride;dipivefrine hydrochloride, (R)-;dipivefrine hydrochloride, (S)-;dipivefrine, (R)-;Dipoquin;Glaucothil;Glaudrops;PMS-Dipivefrin;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+-)-;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (R)-;propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (S)-;Propine;ratio-Dipivefrin

Chemical Property of Dipivefrine hydrochloride, (R)-

Chemical Property:

• PSA: 84.86000
• LogP: 4.03530
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 387.1812508
• Heavy Atom Count: 26
• Complexity: 463

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC1=C(C=C(C=C1)C(CNC)O)OC(=O)C(C)(C)C.Cl
• Isomeric SMILES: CC(C)(C)C(=O)OC1=C(C=C(C=C1)[C@H](CNC)O)OC(=O)C(C)(C)C.Cl

Technology Process of Dipivefrine hydrochloride, (R)-

There total 11 articles about Dipivefrine hydrochloride, (R)- 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:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given;

DOI:10.1002/hlca.19910740216

Reference yield:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19910740216

Reference yield:

dipivefrin hydrochloride (64019-93-8) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With Chiralpak ID; In formic acid; hexane; diethylamine; isopropyl alcohol; at 25 ℃; enantioselective reaction; Resolution of racemate;

DOI:10.1039/C8NJ00685G

upstream raw materials:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol

pivaloyl chloride

4-formyl-1,2-phenylene bis(2,2-dimethylpropanoate)

(R)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>-2-(p-tolylsulfinyl)ethan-1-on

Refernces

• 1、 Solladie-Cavallo,Simon-Wermeister,Farkhani. "Enanthioselective synthesis of both enantioners of a isoproterenol analogue and of di-O-pivaloylepinephrine". . p. 390 - 396. Retrieved 2007/10/02.