Cromakalim

Base Information

• Chemical Name: Cromakalim
• CAS No.: 94535-51-0
• Molecular Formula: C₁₆H₁₈N₂O₃
• Molecular Weight: 286.331
• DSSTox Substance ID: DTXSID001017959,DTXSID301317350
• Nikkaji Number: J386.542H
• Wikipedia: Cromakalim
• Wikidata: Q3698301
• NCI Thesaurus Code: C79109
• Pharos Ligand ID: 8QA58TVYD56T
• ChEMBL ID: CHEMBL11684
• Mol file: 94535-51-0.mol

Synonyms:BRL 38226;BRL 38227;BRL-34915;BRL-38226;BRL-38227;BRL38226;BRL38227;Cromakalim;Cromakalim, (3R-cis)-Isomer;Cromakalim, (3R-trans)-Isomer;Cromakalim, (3S-cis)-Isomer;Cromakalim, (3S-trans)-Isomer;Cromakalim, (trans)-Isomer;Lemakalim;Levcromakalim

Chemical Property of Cromakalim

Chemical Property:

• Melting Point: None °C
• PSA: 73.56000
• LogP: 1.69158
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 286.13174244
• Heavy Atom Count: 21
• Complexity: 481

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C(C2=C(O1)C=CC(=C2)C#N)N3CCCC3=O)O)C
• Isomeric SMILES: CC1([C@@H]([C@H](C2=C(O1)C=CC(=C2)C#N)N3CCCC3=O)O)C

Technology Process of Cromakalim

There total 5 articles about Cromakalim 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:

(3R-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (127419-05-0) + 4-Chlorobutanoyl chloride (4635-59-0) → cromakalim (94535-51-0,148811-94-3)

Guidance literature:

With sodium methylate; triethylamine; In tetrahydrofuran; ethanol; water; ethyl acetate;

Reference yield:

cromakalim (94470-67-4,148811-94-3) → Levcromakalim (94535-50-9,148811-94-3) + cromakalim (94535-51-0,148811-94-3)

Guidance literature:

With N-3,5-dimethylphenylcarbamoyl-derivatized cyclofructan-6 column; In ethanol; n-heptane; trifluoroacetic acid; at 20 ℃; Resolution of racemate;

DOI:10.1021/ac902257a

Reference yield:

3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (65018-90-8) → 3-Hydroxy-2,2-dimethyl-4-(2-oxo-pyrrolidin-1-yl)-chroman-6-carbonitrile (94535-51-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / NaH / dimethylsulfoxide

With sodium hydride; In dimethyl sulfoxide;

DOI:10.1021/jm00161a011

upstream raw materials:

(3R-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

4-Chlorobutanoyl chloride

cromakalim

3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile