1-Butanone, 1-[3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)phenyl]-3-hydroxy-4-( 2-methyl-1,3-dioxolan-2-yl)-

Base Information

• Chemical Name: 1-Butanone, 1-[3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)phenyl]-3-hydroxy-4-( 2-methyl-1,3-dioxolan-2-yl)-
• CAS No.: 95730-74-8
• Molecular Formula: C26H32O7
• Molecular Weight: 456.536
• Mol file: 95730-74-8.mol

Synonyms:

Chemical Property of 1-Butanone, 1-[3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)phenyl]-3-hydroxy-4-( 2-methyl-1,3-dioxolan-2-yl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Butanone, 1-[3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)phenyl]-3-hydroxy-4-( 2-methyl-1,3-dioxolan-2-yl)-

There total 1 articles about 1-Butanone, 1-[3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)phenyl]-3-hydroxy-4-( 2-methyl-1,3-dioxolan-2-yl)- 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: 85.0%

3,3-ethylenedioxybutanal (18871-63-1) + 6-benzyloxy-3,4-dimethoxy-2-(prop-1-enyl)acetophenone (95730-73-7) → 6'benzyloxy-3-hydroxy-3',4'-dimethoxy-4-(2-methyl-1,3-dioxolan-2-yl)-2'-(prop-1-enyl)butyrophenone (95730-74-8)

Guidance literature:

With magnesium; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; -78 degC, 1 h then -78 degC, 3 h;

DOI:10.1039/P19870000389

Reference yield: 99.0%

N-chlorosuccinimide-dimethylsulfide complex (90124-80-4) + 6'benzyloxy-3-hydroxy-3',4'-dimethoxy-4-(2-methyl-1,3-dioxolan-2-yl)-2'-(prop-1-enyl)butyrophenone (95730-74-8) → dimethylsulfonium 1-<3,4-dimethoxy-6-(phenylmethoxy)-2-(1-propenyl)benzoyl>-3-(2-methyl-1,3-dioxolan-2-yl)-2-oxopropylide

Guidance literature:

With triethylamine; In dichloromethane; at -20 ℃;

DOI:10.1039/P19870000389

Reference yield:

6'benzyloxy-3-hydroxy-3',4'-dimethoxy-4-(2-methyl-1,3-dioxolan-2-yl)-2'-(prop-1-enyl)butyrophenone (95730-74-8) → (-)-neurochromenin (479-66-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) N-chlorosuccinimide, dimethyl sulphide, 2.) Zn / 2.) acetic acid

2: 87 percent / dioxane

3: sodium metaperiodate

4: 5percent H₂SO₄-AcOH / tetrahydrofuran / 3 h / Heating

6: 1.) H₂, 5percent HCl, 2.) O₃ / 1.) r.t., 4 d

7: 1.) O₃, 2.) Me₂S

8: sulphamic acid, sodium chlorite

9: H₂SO₄ / acetone

10: 52 percent / AlCl₃, Me₂S / CH₂Cl₂ / -10 °C

11: 68 percent / 5percent HCl / acetone / 24 h / 55 °C

With hydrogenchloride; sodium chlorite; sodium periodate; N-chloro-succinimide; aluminium trichloride; dimethylsulfide; sulfuric acid; aminosulfonic acid; hydrogen; ozone; acetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetone;

DOI:10.1039/c39840001565

upstream raw materials:

3,3-ethylenedioxybutanal

6-benzyloxy-3,4-dimethoxy-2-(prop-1-enyl)acetophenone

Downstream raw materials:

1-<6'-benzyloxy-3',4'-dimethoxy-2'-(prop-1-enyl)phenyl>-4-(2-methyl-1,3-dioxolan-2-yl)butane-1,3-dione

(-)-neurochromenin

1-<6'-benzyloxy-3',4'-dimethoxy-2'-(prop-1-enyl)phenyl>-4-(2-methyl-1,3-dioxolan-2-yl)-2-(methylthiomethyl)butane-1,3-dione

1-<6'-benzyloxy-3',4'-dimethoxy-2-(prop-1-enyl)phenyl>-4-(2-methyl-1,3-dioxolan-2-yl)-2-(methylsulphinylmethyl)butane-1,3-dione

Refernces

• 1、 Yamauchi, Masashige,Katayama, Sadamu,Todoroki, Toshiharu,Watanabe, Toshio. "Total Synthesis of Fulvic Acid". . p. 1565 - 1566. Retrieved 2007/10/02.