6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester

Base Information

• Chemical Name: 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 85293-74-9
• Molecular Formula: C₂₅H₂₈O₅S₂
• Molecular Weight: 472.626
• Mol file: 85293-74-9.mol

Synonyms:6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property of 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester

There total 6 articles about 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester 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%

2-Methyl-2-(1-methylene-allyl)-[1,3]dithiolane (85293-68-1) + (E)-4-(1,4-Dimethoxy-naphthalen-2-yl)-4-oxo-but-2-enoic acid methyl ester (85293-72-7) → 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester (85293-74-9)

Guidance literature:

In toluene; for 60h; Heating;

DOI:10.1021/jo00157a039

Reference yield:

1,4-dimethoxynaphthalene (10075-62-4) → 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester (85293-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / AlCl₃ / various solvent(s) / Ambient temperature

2: 1.) Br₂, 2.) Et₃N / 1.) CCl₄, room temp., 4 h, 2.) CCl₄, room temp.

3: 70 percent / toluene / 60 h / Heating

With aluminium trichloride; bromine; triethylamine; In toluene;

DOI:10.1021/jo00157a039

Reference yield:

2-(2-methyl-1,3-dithiolan-2-yl)acetaldehyde (65726-46-7) → 6-(1,4-Dimethoxy-naphthalene-2-carbonyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-cyclohex-3-enecarboxylic acid methyl ester (85293-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / acetic acid / CHCl₃

2: 60 percent / n-butyllithium / tetrahydrofuran

3: 70 percent / toluene / 60 h / Heating

With n-butyllithium; acetic acid; In tetrahydrofuran; chloroform; toluene;

DOI:10.1021/jo00157a039

upstream raw materials:

2-Methyl-2-(1-methylene-allyl)-[1,3]dithiolane

(E)-4-(1,4-Dimethoxy-naphthalen-2-yl)-4-oxo-but-2-enoic acid methyl ester

1,4-dimethoxynaphthalene

2-(2-methyl-1,3-dithiolan-2-yl)acetaldehyde

Downstream raw materials:

4-Acetyl-2-(1,4-dimethoxy-naphthalene-2-carbonyl)-cyclohexanecarboxylic acid methyl ester

4-Acetyl-2-(1,4-dimethoxy-naphthalene-2-carbonyl)-cyclohexanecarboxylic acid

2-acetyl-1,2,3,4,6,11-hexahydro-5,12-dihydroxynaphthacene-6,11-quinone

4-Acetyl-6-(1,4-dimethoxy-naphthalene-2-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester