7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one

Base Information

• Chemical Name: 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one
• CAS No.: 477-27-0
• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.417
• Hs Code.: 2924299090
• NSC Number: 371715
• Wikidata: Q105213678
• Metabolomics Workbench ID: 155530
• ChEMBL ID: CHEMBL323668
• Mol file: 477-27-0.mol

Synonyms:O-Demethylcolchicine;7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one;N-(10-hydroxy-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)acetamide;MLS001202244;N-(10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide;SMR000564997;O(sup 10)-Demethylcolchicine;Colchiceine (VAN);EINECS 207-512-5;NSC 123396;7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo(a)heptalen-9(5H)-one;BRN 2824078;C21H23NO6;MFCD00598980;cid_10156;SCHEMBL177859;CHEMBL323668;BDBM66784;HMS1648C14;HMS3340L13;N-[(7S,12aRa)-10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (Colchiceine);STR08954;NSC371715;STL373174;AKOS001580935;AKOS017342895;DB15534;NSC-371715;NCGC00095943-01;LS-54657;FT-0665154;AB00830015-06;EN300-22939293;N-(10-hydroxy-9-keto-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl)acetamide;N-(1,2,3-trimethoxy-10-oxidanyl-9-oxidanylidene-6,7-dihydro-5H-benzo[a]heptalen-7-yl)ethanamide;N-{14-hydroxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0(2),?]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl}acetamide;N-{14-hydroxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0,2,7]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl}acetamide

Chemical Property of 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one

Chemical Property:

• Vapor Pressure: 1.83E-22mmHg at 25°C
• Melting Point: 172-1740C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 731.5°Cat760mmHg
• PKA: 7.59±0.40(Predicted)
• Flash Point: 396.2°C
• PSA: 94.09000
• Density: 1.31g/cm³
• LogP: 2.95950
• Storage Temp.: Refrigerator
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 385.15253745
• Heavy Atom Count: 28
• Complexity: 724

Purity/Quality:

99%, ^*data from raw suppliers

Colchiceine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)O)OC)OC)OC
• Uses: A metabolite of Colchicine

Technology Process of 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one

There total 33 articles about 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one 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: 98.0%

colchicine (64-86-8,54192-66-4) → colchiceine (477-27-0,1990-46-1)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 100 ℃; for 3h;

DOI:10.1134/S1070428016080078

Reference yield:

10-(trifluoroacetyl)colchiceinamide (136570-06-4) → colchiceine (477-27-0,1990-46-1)

Guidance literature:

With sodium hydroxide; at 90 ℃; for 24h;

DOI:10.1021/jm00115a026

Reference yield:

N-[(7S)-1,2,3-trimethoxy-9-oxo-10-amino-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3123-89-5) → colchiceine (477-27-0,1990-46-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 mg / Na₂CO₃ / diethyl ether / 1 h / Ambient temperature

2: 12 mg / 1 N NaOH / 24 h / 90 °C

With sodium hydroxide; sodium carbonate; In diethyl ether;

DOI:10.1021/jm00115a026

upstream raw materials:

colchicine

10-(trifluoroacetyl)colchiceinamide

trimethylcolchicinic acid

acetic anhydride

Downstream raw materials:

colchicine

(7S)-isocolchicine

10-ethoxy-10-demethoxycolchicine

Ethyl isocolchicinate

Refernces

• 1、 Shchegravina, Ekaterina S.,Tretiakova, Daria S.,Alekseeva, Anna S.,Galimzyanov, Timur R.,Utkin, Yuri N.,Ermakov, Yuri A.,Svirshchevskaya, Elena V.,Negrebetsky, Vadim V.,Karpechenko, Natalia Yu.,Chernikov, Valery P.,Onishchenko, Natalia R.,Vodovozova, Elena L.,Fedorov, Alexey Yu.,Boldyrev, Ivan A.. "Phospholipidic Colchicinoids as Promising Prodrugs Incorporated into Enzyme-Responsive Liposomes: Chemical, Biophysical, and Enzymological Aspects". . p. 1098 - 1113. Retrieved 2019/03/26.
• 2、 Bukhvalova, S. Yu.,Maleev,Gracheva, Yu. A.,Voitovich, Yu. V.,Ignatov,Svirshchevskaya,Fedorov, A. Yu.. "Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine". . p. 2205 - 2215. Retrieved 2020/02/15.