e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Journal of Organic Chemistry

2, 4-Dihydroxyphenanthrenes and derived ethers. Regioselective etherification of acetates

HE Zaugg, DA Dunnigan

Index: Zaugg,H.E.; Dunnigan,D.A. Journal of Organic Chemistry, 1976 , vol. 41, # 21 p. 3415 - 3419

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Citation Number: 0

Abstract

Etherification of the two phenanthrene diacetates 3 and 11 using a large alkyl halide in the presence of anhydrous KzC09 in refluxing dry acetone is much more regioselective at the 2 position than is the direct alkylation of the monosodium salts of the corresponding phenanthrenediols 2 and 10. However, this regioselectivity unaccountably disappears when methyl iodide is used as the alkylating agent. Also, when the steric hindrance provided by ...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

ethyl 2,4-dihydroxyphenanthrene-3-carboxylate Structure

ethyl 2,4-dihyd...

~%

ethyl 2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylate Structure

ethyl 2-(3-(4-f...

3-Phenanthrenecarboxylicacid, 2,4-bis[3-(4-fluorophenyl)propoxy]-, ethyl ester Structure

3-Phenanthrenec...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

2,4-dioctoxyphenanthrene Structure

2,4-dioctoxyphe...

1-Bromooctane Structure

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

2,4-dioctoxyphenanthrene Structure

2,4-dioctoxyphe...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

ethyl 2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylate Structure

ethyl 2-(3-(4-f...

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

ethyl 2,4-dihydroxyphenanthrene-3-carboxylate Structure

ethyl 2,4-dihyd...

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylic acid Structure

2-(3-(4-fluorop...

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylic acid Structure

2-(3-(4-fluorop...

~%

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

~%

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

ethyl 2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylate Structure

ethyl 2-(3-(4-f...

~%

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

ethyl 2,4-dihydroxyphenanthrene-3-carboxylate Structure

ethyl 2,4-dihyd...

~%

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

N/A Structure

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

Ethanoic anhydride Structure

Ethanoic anhydride

~%

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

1-Bromooctane Structure

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

ethyl 4-acetoxy-2-(octyloxy)phenanthrene-3-carboxylate Structure

ethyl 4-acetoxy...

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

3-(ethoxycarbonyl)phenanthrene-2,4-diyl diacetate Structure

3-(ethoxycarbon...

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

2-(octyloxy)phenanthren-4-ol Structure

2-(octyloxy)phe...

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

~%

(2-octoxy-9,10-dihydrophenanthren-4-yl) acetate Structure

(2-octoxy-9,10-...

1-(3-Bromopropyl)-4-fluorobenzene Structure

1-(3-Bromopropy...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

[2-[3-(4-fluorophenyl)propoxy]phenanthren-4-yl] acetate Structure

[2-[3-(4-fluoro...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylic acid Structure

2-(3-(4-fluorop...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

2-(3-(4-Fluorophenyl)propoxy)-4-phenanthrenol Structure

2-(3-(4-Fluorop...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

3-(ethoxycarbonyl)phenanthrene-2,4-diyl diacetate Structure

3-(ethoxycarbon...

~%

ethyl 2,4-diacetyloxy-9,10-dihydrophenanthrene-3-carboxylate Structure

ethyl 2,4-diace...

ethyl 2,4-dihydroxyphenanthrene-3-carboxylate Structure

ethyl 2,4-dihyd...

~%

ethyl 2,4-diacetyloxy-9,10-dihydrophenanthrene-3-carboxylate Structure

ethyl 2,4-diace...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

ethyl 2-(3-(4-fluorophenyl)propoxy)-4-hydroxyphenanthrene-3-carboxylate Structure

ethyl 2-(3-(4-f...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

ethyl 2,4-dihydroxyphenanthrene-3-carboxylate Structure

ethyl 2,4-dihyd...

~%

4-Phenanthrenol,2-[3-(4-fluorophenyl)propoxy]-9,10-dihydro-, 4-acetate Structure

4-Phenanthrenol...

1-Bromooctane Structure

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

3-(ethoxycarbonyl)phenanthrene-2,4-diyl diacetate Structure

3-(ethoxycarbon...

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

2,4-Phenanthrenediol Structure

2,4-Phenanthrenediol

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

1-Bromooctane Structure

2,4-Phenanthrenediol,2,4-diacetate Structure

2,4-Phenanthren...

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

2,4-dioctoxyphenanthrene Structure

2,4-dioctoxyphe...

ethyl 4-acetoxy-2-(octyloxy)phenanthrene-3-carboxylate Structure

ethyl 4-acetoxy...

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...

2-(octyloxy)phenanthren-4-ol Structure

2-(octyloxy)phe...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

4-Phenanthrenol,2-(octyloxy)-, 4-acetate Structure

4-Phenanthrenol...