Efonidipine

Base Information

• Chemical Name: Efonidipine
• CAS No.: 111011-63-3
• Molecular Formula: C34H38 N3 O7 P
• Molecular Weight: 631.665
• UNII: 40ZTP2T37Q
• DSSTox Substance ID: DTXSID9043988
• Wikipedia: Efonidipine
• Wikidata: Q5347555,Q106574688
• NCI Thesaurus Code: C73026
• Pharos Ligand ID: RJKK67JP4Y39
• Metabolomics Workbench ID: 152267
• ChEMBL ID: CHEMBL2074922
• Mol file: 111011-63-3.mol

Synonyms:5-(5,5-dimethyl-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid, 2-(phenyl(phenylmethyl)amino) ethyl ester, P-oxide, hydrochloride;efonidipine;enfonidipine hydrochloride;NZ 105;NZ-105

Chemical Property of Efonidipine

Chemical Property:

• Melting Point: 169-170℃
• Boiling Point: 746.9°Cat760mmHg
• PKA: 4.03±0.50(Predicted)
• Flash Point: 405.5°C
• PSA: 132.73000
• Density: 1.3g/cm³
• LogP: 8.15520
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 631.24473756
• Heavy Atom Count: 45
• Complexity: 1170

Purity/Quality:

99%, ^*data from raw suppliers

Efonidipine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)P2(=O)OCC(CO2)(C)C)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OCCN(CC4=CC=CC=C4)C5=CC=CC=C5
• Recent ClinicalTrials: Role of Calcium Channels in Vascular Function
• Recent NIPH Clinical Trials: Effects of combination therapy with efonidipine or cilnidipine added on ARB on renal outcomes in hypertensive patients with CKD and proteinuria

Technology Process of Efonidipine

There total 5 articles about Efonidipine 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: 45.0%

2-ethyl 3-aminocrotonate (111011-79-1) + 5,5-dimethyl-2-<1-(3-nitrophenyl)-3-oxo-1-buten-2-yl>-2-oxo-1,3,2-dioxaphosphorinane (111011-78-0) → efonidipine (111011-63-3)

Guidance literature:

In toluene; for 5h; Heating;

DOI:10.1248/cpb.40.2362

Reference yield:

2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (1005-69-2) → efonidipine (111011-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65.8 percent / diethyl ether / 7 h / Heating

2: 31 percent / piperidine, acetic acid / benzene / 6.5 h / Heating

3: 45 percent / toluene / 5 h / Heating

With piperidine; acetic acid; In diethyl ether; toluene; benzene;

DOI:10.1248/cpb.40.2362

Reference yield:

2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane (111011-80-4) → efonidipine (111011-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / piperidine, acetic acid / benzene / 6.5 h / Heating

2: 45 percent / toluene / 5 h / Heating

With piperidine; acetic acid; In toluene; benzene;

DOI:10.1248/cpb.40.2362

upstream raw materials:

2-ethyl 3-aminocrotonate

5,5-dimethyl-2-<1-(3-nitrophenyl)-3-oxo-1-buten-2-yl>-2-oxo-1,3,2-dioxaphosphorinane

2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane

2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane

Refernces

• 1、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.
• 2、 Sakoda,Kamikawaji,Seto. "Synthesis of 1,4-dihydropyridine-5-phosphonates and their calcium-antagonistic and antihypertensive activities". . p. 2362 - 2369. Retrieved 2007/10/02.