7C-aglycone

Base Information

• Chemical Name: 7C-aglycone
• CAS No.: 51732-61-7
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.339
• Metabolomics Workbench ID: 38545
• Mol file: 51732-61-7.mol

Synonyms:7C-aglycone;CHEBI:89489;CHEBI:166699;Q27161681;(Z)-4-methyl-6-(3-methyl-1,4-dioxonaphthalen-2-yl)hex-4-enoic acid;6-(1,4-dihydro-3-methyl-1,4-dioxo-2-naphthalenyl)-4-methyl- 4-Hexenoate;(4Z)-4-methyl-6-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)hex-4-enoic acid;6-(1,4-dihydro-3-methyl-1,4-dioxo-2-naphthalenyl)-4-methyl- 4-Hexenoic acid

Chemical Property of 7C-aglycone

Chemical Property:

• Vapor Pressure: 1.03E-10mmHg at 25°C
• Boiling Point: 497.4°C at 760 mmHg
• Flash Point: 268.7°C
• PSA: 71.44000
• Density: 1.209g/cm³
• LogP: 3.58330
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 298.12050905
• Heavy Atom Count: 22
• Complexity: 553

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC(=O)O
• Isomeric SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(/C)\CCC(=O)O

Technology Process of 7C-aglycone

There total 22 articles about 7C-aglycone 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: 70.0%

trans-2-methyl-3-(5'-formyl-3'-methylpent-2'-enyl)-1,4-naphthoquinone → 3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone (34185-71-2,51732-61-7)

Guidance literature:

With oxone; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1055/s-0034-1380002

Reference yield:

NaQuinate-Me (34207-04-0) → 3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone (34185-71-2,51732-61-7)

Guidance literature:

With water; potassium hydroxide;

Reference yield:

C16H14O2 → 3-(5-carboxy-3-methyl-(2E)-penten-1-yl)-2-methyl-1,4-naphthoquinone (34185-71-2,51732-61-7)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium tert-butylate / tetrahydrofuran / 4 - 20 °C / Inert atmosphere

2: dodecyltrimethylammonium bromide / acetic acid / 1.5 h / 90 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 - 20 °C / Inert atmosphere

4: periodic acid / water; tetrahydrofuran-d8 / 1 h / 20 °C / Inert atmosphere

5: oxone / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

With oxone; potassium tert-butylate; dodecyltrimethylammonium bromide; periodic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; tetrahydrofuran-d8; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1055/s-0034-1380002

upstream raw materials:

4-acetoxy-3-methyl-1-naphthol

methyl (E)-6-hydroxy-4-methylhex-4-enoate

trans-1-Acetoxy-4-hydroxy-2-methyl-3-(5',5'-diethoxycarbonyl-3'-methyl-2'-pentenyl)-naphthalene

3-(5-carbomethoxy-3-methyl-(2E)-penten-yl)-1,4-dimethoxy-2-methylnaphthalene

Refernces

• 1、 Teitelbaum, Aaron M.,Scian, Michele,Nelson, Wendel L.,Rettie, Allan E.. "Efficient Syntheses of Vitamin K Chain-Shortened Acid Metabolites". . p. 944 - 948. Retrieved 2015/03/30.
• 2、 Watanabe,Okamoto,Imada,Morimoto. "Ubiquinone and related compounds. XXXI. Synthesis of urinary metabolites of ubiquinone, phylloquinone, α-tocopherol and their related compounds". . p. 774 - 783. Retrieved 2007/10/07.