Methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Base Information

• Chemical Name: Methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
• CAS No.: 16234-96-1
• Molecular Formula: C22H20 O8
• Molecular Weight: 412.396
• NSC Number: 114780
• DSSTox Substance ID: DTXSID20936695
• Nikkaji Number: J254.473C
• Wikidata: Q104196405
• Mol file: 16234-96-1.mol

Synonyms:methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate;NSC-114780;SCHEMBL11065224;DTXSID20936695;NSC114780;1-Naphthacenecarboxylic acid,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-, methyl ester, (1R,2R,4S)-;1-Naphthacenecarboxylic acid,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-, methyl ester, [1R-(1.alpha.,2.beta.,4.beta.)]-

Chemical Property of Methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Chemical Property:

• Vapor Pressure: 1.64E-18mmHg at 25°C
• Boiling Point: 663.5°Cat760mmHg
• PKA: 6.50±0.70(Predicted)
• Flash Point: 235°C
• PSA: 141.36000
• Density: 1.525g/cm³
• LogP: 1.70800
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 412.11581759
• Heavy Atom Count: 30
• Complexity: 737

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O)O

Technology Process of Methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

There total 92 articles about Methyl 2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate 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: 100.0%

aclacinomycin A (57576-44-0) → (+)-aklavinone (16234-96-1)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃;

DOI:10.1021/acs.jmedchem.0c01191

Reference yield: 90.0%

9-epi-aklavinone 7-methyl ether (78773-17-8,78773-18-9,78773-19-0,78773-20-3) → (+/-)-Aklavinon-I (16234-96-1,19260-54-9,53526-60-6,53526-61-7,78773-25-8,78821-97-3,78821-98-4,78821-99-5,88198-76-9,88391-16-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1021/ja00404a047

Reference yield: 88.0%

(+/-)-7-deoxyalkavinone (19260-55-0) → aklavinone (16234-96-1,19260-54-9,53526-60-6,53526-61-7,78773-25-8,78821-97-3,78821-98-4,78821-99-5,88198-76-9,88391-16-6)

Guidance literature:

With bromine; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 70 ℃; for 1h;

DOI:10.1016/S0040-4020(01)91531-5

upstream raw materials:

(1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

{4,5-Dihydroxy-3-[(S)-1-((1R,2R)-2-hydroxy-1-methyl-propoxy)-3-oxo-pentyl]-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-acetic acid methyl ester

(1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((1R,2R)-2-hydroxy-1-methyl-propoxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

(3-Formyl-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetic acid methyl ester

Downstream raw materials:

aklavin

3',3'-didesmethyl-aclarubicin

(1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

(1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

Refernces

Syntheses, Kinetics, and Mechanism of Formation of Polynuclear Hydroxo-Bridged Complexes of (trans-1,2-Diaminocyclohexane)platinum(II)

10.1021/ja00381a016

The research investigates the properties and synthesis of various chemical compounds. One study examines the mixed-valence compound Eu3S4, analyzing its spectroscopic characteristics, thermal barrier, and intervalence transfer band using techniques like Mossbauer simulations and time domain reflectrometry (TDR). Another study focuses on the synthesis, kinetics, and mechanism of formation of polynuclear hydroxo-bridged complexes of (trans-1,2-diaminocyclohexane)platinum(II), exploring how these complexes form under different pH conditions and their 195Pt NMR chemical shifts. Additionally, a study reports an efficient total synthesis of (f)-aklavinone, an anthracyclinone antitumor agent, starting from 1,3-cyclohexadione and involving key steps such as a Diels-Alder condensation and a stereoselective aldol condensation. These studies collectively highlight the roles of various chemicals and reactions in understanding and synthesizing complex compounds with potential applications in materials science and medicine.