N-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide

Base Information

• Chemical Name: N-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide
• CAS No.: 163163-24-4
• Molecular Formula: C₁₅H₂₀N₂O₄S
• Molecular Weight: 324.401
• European Community (EC) Number: 634-078-8
• DSSTox Substance ID: DTXSID60349649
• Nikkaji Number: J1.485.486J
• Wikidata: Q27116269
• ChEMBL ID: CHEMBL338273
• Mol file: 163163-24-4.mol

Synonyms:293B cpd;6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethylchromane;6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethylchromane, (trans-(+))-isomer;6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethylchromane, (trans-(-))-isomer;chromanol 293B

Chemical Property of N-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide

Chemical Property:

• Appearance/Colour: White solid
• Boiling Point: 474.1 °C at 760 mmHg
• Flash Point: 240.6 °C
• PSA: 99.01000
• Density: 1.33 g/cm³
• LogP: 2.49358
• Storage Temp.: −20°C
• Solubility.: DMSO: 18 mg/mL
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 324.11437830
• Heavy Atom Count: 22
• Complexity: 560

Purity/Quality:

98%Min ^*data from raw suppliers

(-)-[3R,4S]-Chromanol293B ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCS(=O)(=O)N(C)C1C(C(OC2=C1C=C(C=C2)C#N)(C)C)O

Technology Process of N-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide

There total 12 articles about N-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide 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: 87.0%

N-((3R,4S)-6-cyano-3-methoxy-2,2-dimethylchroman-4-yl)-N-methylethanesulfonamide → (-)-Chromanol 293B (163163-23-3,163163-24-4)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151431

Reference yield:

N-methyl-ethanesulfonamide (6601-37-2) + (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile (65018-90-8,75611-72-2,114926-02-2,114926-03-3) → (-)-Chromanol 293B (163163-23-3,163163-24-4)

Guidance literature:

N-methyl-ethanesulfonamide; With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 0.333333h;

(1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile; In dimethyl sulfoxide; at 20 - 45 ℃; Further stages.;

DOI:10.1021/jm0109255

Reference yield:

2-hydroxy-5-cyanoacetophenone (35794-84-4) → (-)-Chromanol 293B (163163-23-3,163163-24-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyrrolidine / acetonitrile / 8 h / 45 °C

2.1: NaBH₄ / methanol / 20 °C

3.1: p-TsOH*H₂O / toluene / 22 h / 100 °C

4.1: (R,R)-Jacobsen-Catalyst; NaOCl; disodium hydrogen phosphate / CH₂Cl₂ / 1 h / pH 11.3

5.1: NaH / dimethylsulfoxide / 0.33 h / 20 °C

5.2: dimethylsulfoxide / 20 - 45 °C

With pyrrolidine; sodium hypochlorite; sodium tetrahydroborate; disodium hydrogenphosphate; R,R-Jacobsen's catalyst; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1021/jm0109255

upstream raw materials:

N-methyl-ethanesulfonamide

(1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile

N-methyl-N-trimethylsilyl-ethanesulfonamide

2-hydroxy-5-cyanoacetophenone

Refernces

• 1、 Gerlach,Brendel,Lang,Paulus,Weidmann,Brüggemann,Busch,Suessbrich,Bleich,Greger. "Synthesis and activity of novel and selective Iks-channel blockers". . p. 3831 - 3837. Retrieved 2007/10/03.