Dehydroxymethylepoxyquinomicin

Base Information

• Chemical Name: Dehydroxymethylepoxyquinomicin
• CAS No.: 287194-40-5
• Molecular Formula: C13H11NO5
• Molecular Weight: 261.234
• DSSTox Substance ID: DTXSID00432307
• Nikkaji Number: J1.312.229F
• Wikidata: Q82246380
• ChEMBL ID: CHEMBL169300
• Mol file: 287194-40-5.mol

Synonyms:dehydroxymethylepoxyquinomicin;DHMEQ cpd

Chemical Property of Dehydroxymethylepoxyquinomicin

Chemical Property:

• PSA: 102.65000
• LogP: 0.29170
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 261.06372245
• Heavy Atom Count: 19
• Complexity: 446

Purity/Quality:

98.5% ^*data from raw suppliers

(-)-DHMEQ 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)NC2=CC(=O)C3C(C2O)O3)O
• Isomeric SMILES: C1=CC=C(C(=C1)C(=O)NC2=CC(=O)[C@@H]3[C@H]([C@H]2O)O3)O

Technology Process of Dehydroxymethylepoxyquinomicin

There total 12 articles about Dehydroxymethylepoxyquinomicin 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%

2-(tert-butyl-dimethyl-silanyloxy)-N-(2-hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-benzamide → (-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide (287194-40-5,287194-41-6,287194-38-1,326499-51-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0960-894X(00)00114-1

Reference yield: 69.0%

2,3-epoxy-4-hexanoyloxy-5-[(2-hexanoyloxybenzoyl)amino]cyclohex-5-en-1-one → C19H21NO6 (1313573-75-9) + (-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide (287194-40-5,287194-41-6,287194-38-1,326499-51-8)

Guidance literature:

With Burkholderia cepacia lipase; water; In acetone; at 20 ℃; for 24h; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2010.07.013

Reference yield:

(2S,3R)-2,3-epoxy-5-[(2-hydroxybenzoyl)amino]cyclohex-5-ene-1,4-dione (1246285-28-8) → (-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide (287194-40-5,287194-41-6,287194-38-1,326499-51-8)

Guidance literature:

With sodium tris(acetoxy)borohydride; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tet.2010.07.013

upstream raw materials:

2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide

N-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide

N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide

acetic acid 2-(2,5-dimethoxyphenylcarbamoyl)phenyl ester

Downstream raw materials:

C₂₂H₂₈N₂O₉S

C₂₀H₁₉NO₅S

C₂₂H₂₈N₂O₉S

C₂₀H₁₉NO₅S

Refernces

• 1、 Suzuki, Yoshikazu,Sugiyama, Chie,Ohno, Osamu,Umezawa, Kazuo. "Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor". . p. 7061 - 7066. Retrieved 2007/10/03.