Midafotel

Base Information

• Chemical Name: Midafotel
• CAS No.: 117414-74-1
• Molecular Formula: C₈H₁₅N₂O₅P
• Molecular Weight: 250.191
• UNII: 7LYU6ZF84G
• DSSTox Substance ID: DTXSID1045740
• Nikkaji Number: J366.386H,J386.728E
• Wikipedia: Midafotel
• Wikidata: Q76327378
• NCI Thesaurus Code: C167034
• ChEMBL ID: CHEMBL90564
• Mol file: 117414-74-1.mol

Synonyms:3-(2-carboxypiperazine-4-yl)-1-propenyl-1-phosphonic acid;4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid;cppene;D-CPP-ene;SDZ EAA 494;SDZ EAA 494, (E)-isomer;SDZ EAA 494, (R-(E))-isomer;SDZ EAA 494, (S-(E))-isomer

Chemical Property of Midafotel

Chemical Property:

• Vapor Pressure: 8.31E-14mmHg at 25°C
• Boiling Point: 555.6°C at 760 mmHg
• Flash Point: 289.8°C
• PSA: 119.91000
• Density: 1.449g/cm³
• LogP: -0.69710
• Storage Temp.: Desiccate at RT
• XLogP3: -7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 250.07185858
• Heavy Atom Count: 16
• Complexity: 326

Purity/Quality:

98%min ^*data from raw suppliers

D-CPP-ene ^*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)CC=CP(=O)(O)O
• Isomeric SMILES: C1CN(C[C@@H](N1)C(=O)O)C/C=C/P(=O)(O)O
• Uses: D-CPP-ene is a potent, competitive NMDA antagonist (1). NMDA antagonists such as this may increase sucrose intake through hunger satiation delay (2).

Technology Process of Midafotel

There total 3 articles about Midafotel 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: 58.0%

(R,E)-4-<3-(diethoxyphosphinyl)prop-2-enyl>piperazine-2-carboxylic acid (117414-78-5) → (R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid (117414-74-1,137424-80-7)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1002/hlca.19890720522

Reference yield:

(R)-Piperazine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester → (R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid (117414-74-1,137424-80-7)

Guidance literature:

Multi-step reaction with 3 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

With trimethylsilyl bromide; boron trichloride; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19890720522

Reference yield:

menthyl (R,E)-4-<3-(diethoxyphosphinyl)por-2-enyl>piperazine-2-carboxylate → (R,E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic acid (117414-74-1,137424-80-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 58 percent / bromotrimethylsilane / CH₂Cl₂ / 16 h / Ambient temperature

With trimethylsilyl bromide; boron trichloride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19890720522

upstream raw materials:

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

Downstream raw materials:

(R)-[3-(2-carboxypiperazin-4-yl)propyl]phosphonic acid