(2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid

Base Information

• Chemical Name: (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid
• CAS No.: 126453-07-4
• Molecular Formula: C₈H₁₇N₂O₅P
• Molecular Weight: 252.207
• UNII: A3QV2VT7SN
• DSSTox Substance ID: DTXSID501208909
• Nikkaji Number: J259.993G
• ChEMBL ID: CHEMBL47277
• Mol file: 126453-07-4.mol

Synonyms:(R)-CPP;126453-07-4;(2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid;(R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid;A3QV2VT7SN;CHEMBL47277;2-Piperazinecarboxylic acid, 4-(3-phosphonopropyl)-, (2R)-;CPP, (R)-;CPP, (-)-;3-((R)-2-Carboxypiperazin-4-yl)-propyl-1-phosphonic acid;3-(2-Carboxypiperazin-4-yl)propyl-1-phosphonic acid, (R)-;7RC;Tocris-0173;Tocris-0247;Lopac-C-104;UNII-A3QV2VT7SN;SCHEMBL1557957;(-)-CPP;CUVGUPIVTLGRGI-SSDOTTSWSA-N;DTXSID501208909;BDBM50050704;HB0021;AKOS024457118;NCGC00015179-01;NCGC00015179-02;NCGC00024482-01;NCGC00024515-01;BC168104;HY-100814;LS-110988;CS-0020456;SR-01000597718;J-005384;SR-01000597718-1;(R)-4-(3-phosphonopropyl)piperazine-2-carboxylicacid;(2R)-4-(3-Phosphonopropyl)-2-piperazinecarboxylic acid;(R)-4-(3-Phosphono-propyl)-piperazine-2-carboxylic acid;3-((R)-Carboxylpiperazin-4-yl)-propyl-1-phosphonic acid

Chemical Property of (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.14E-13mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 546.7°C at 760 mmHg
• PKA: 1.89±0.20(Predicted)
• Flash Point: 284.4°C
• PSA: 119.91000
• Density: 1.408g/cm³
• LogP: -0.82070
• Storage Temp.: Desiccate at RT
• XLogP3: -6.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 252.08750864
• Heavy Atom Count: 16
• Complexity: 292

Purity/Quality:

98% or more ^*data from raw suppliers

(R)-CPP ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC(N1)C(=O)O)CCCP(=O)(O)O
• Isomeric SMILES: C1CN(C[C@@H](N1)C(=O)O)CCCP(=O)(O)O
• Description: (R)-CPP is an NMDA receptor antagonist (Ki = 0.14 μM). It binds to NMDA receptors containing GluN2A, GluN2B, GluN2C, and GluN2D subunits with Ki values of 0.04, 0.3, 0.6, and 2 μM, respectively. It inhibits depolarization induced by NMDA in isolated hemisected frog spinal cord (pA2 = 6.56) and NMDA-induced sodium efflux from rat brain slices (pA2 = 6.2). (R)-CPP inhibits the clonic phase of sound-induced seizures in DBA/2 mice (ED50 = 65.8 μmol/kg) and the myoclonic phase of stroboscopic-induced seizures in P. papio photosensitive baboons (ED50 = 127 μmol/kg).
• Uses: (R)-CPP is a piperazine derivative demonstrating highly potent NMDA receptor antagonism.

Technology Process of (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid

There total 4 articles about (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid 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: 75.0%

(R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid (117414-74-1,137424-80-7) → (R)-[3-(2-carboxypiperazin-4-yl)propyl]phosphonic acid (126453-07-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ammonium hydroxide; Ambient temperature;

DOI:10.1002/hlca.19890720522

Reference yield:

(R)-Piperazine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester → (R)-[3-(2-carboxypiperazin-4-yl)propyl]phosphonic acid (126453-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / Et₃N / tetrahydrofuran / 20 h / -25 °C

2: 6.21 g / BCl₃ / CH₂Cl₂; 1,2-dichloro-ethane / 1.) -25 deg C, 1h, 2.) 0 deg C, 3.5h

3: 58 percent / bromotrimethylsilane / CH₂Cl₂ / 16 h / Ambient temperature

4: 75 percent / hydrogen / 10percent Pd/C / aq. NH₃ / Ambient temperature

With trimethylsilyl bromide; hydrogen; boron trichloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ammonium hydroxide; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19890720522

Reference yield:

(R,E)-4-<3-(diethoxyphosphinyl)prop-2-enyl>piperazine-2-carboxylic acid (117414-78-5) → (R)-[3-(2-carboxypiperazin-4-yl)propyl]phosphonic acid (126453-07-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / bromotrimethylsilane / CH₂Cl₂ / 16 h / Ambient temperature

2: 75 percent / hydrogen / 10percent Pd/C / aq. NH₃ / Ambient temperature

With trimethylsilyl bromide; hydrogen; palladium on activated charcoal; In ammonium hydroxide; dichloromethane;

DOI:10.1002/hlca.19890720522

upstream raw materials:

(R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid

(R,E)-4-<3-(diethoxyphosphinyl)prop-2-enyl>piperazine-2-carboxylic acid

Refernces