604-82-0

Usage

Uses

Used in Pharmaceutical Industry:
(4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one is used as a potential pharmaceutical candidate for various applications due to its complex structure and functional groups that may interact with biological receptors and enzymes. Further research and testing are required to explore its potential uses and to ensure its safety and effectiveness.

Synthetic route

Estrone (53-16-7) → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0)

Conditions	Yield
With calcium tetrakis(pentafluorophenyl)borate undecahydrate; dihydrogen peroxide; oxalic acid In 1,2-dichloro-ethane at 50℃; for 4h; Baeyer-Villiger Ketone Oxidation; regioselective reaction;	88%

C17H21O4(1-)*Na(1+) → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0)

Conditions	Yield
With hydrogenchloride	84%

3-acetoxy-17a-oxa-D-homo-estra-1,3,5(10)-trien-17-one (5128-18-7) → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0)

Conditions	Yield
With sodium hydroxide Behandeln der Reaktionsloesung mit Kohlendioxid und anschliessendes Ansaeuern mit wss. Salzsaeure;

3-hydroxy-estra-1,3,5(10)-trien-17-one → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide Ansaeuern des Reaktionsgemisches mit wss. Salzsaeure;

3-acetoxy-17,17-bis-hydroperoxy-estra-1,3,5(10)-triene → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) + 3-hydroxy-17a-oxa-D-homo-13α-estra-1,3,5(10-trien-17-one

Conditions	Yield
With toluene Erwaermen des Reaktionsgemisches mit wss.-methanol. Natronlauge und anschliessendes Ansaeuern mit wss. Salzsaeure;

3-acetoxy-17,17-bis-hydroperoxy-estra-1,3,5(10)-triene → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) + 3-hydroxy-17a-oxa-D-homo-13α-estra-1,3,5(10)-trien-17-one (604-82-0, 6869-53-0)

Conditions	Yield
With toluene Erwaermen des Reaktionsgemisches mit wss.-methanol. Natronlauge und anschliessendes Ansaeuern mit wss. Salzsaeure;

estrone acetate (901-93-9) → (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; aqueous hydrogen peroxide / unter Lichtausschluss 2: aqueous methanol. NaOH-solution / Behandeln der Reaktionsloesung mit Kohlendioxid und anschliessendes Ansaeuern mit wss. Salzsaeure View Scheme

(4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) → 17-oxo-17a-homo-17a-oxaestra-1,3,5(10)-trien-3-yl sulfamate

Conditions	Yield
With sulphamoyl chloride In N,N-dimethyl acetamide at 0 - 20℃; for 6h; sulfamoylation;	89%
With sulphamoyl chloride; sodium hydride In DMF (N,N-dimethyl-formamide); toluene at 20℃;	54%

(4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) + formic acid ethyl ester (109-94-4) → 3-hydroxy-16-(hydroxymethylene)-17-oxo-17a-oxa-D-homo-estra-1,3,5(10)-triene (95237-26-6)

Conditions	Yield
In N,N-dimethyl-formamide	76%

benzoyl chloride (98-88-4) + (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) → 3-benzoyloxy-17a-oxa-D-homo-estra-1,3,5(10)-trien-17-one

Conditions	Yield
With pyridine

propionic acid anhydride (123-62-6) + (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) → 3-propionyloxy-17a-oxa-D-homo-estra-1,3,5(10)-trien-17-one

Conditions	Yield
With pyridine

dimethyl sulfate (77-78-1) + (4aS,4bR,10bS,12aS)-8-hydroxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromen-2-one (604-82-0) → 3-methoxy-17a-oxa-D-homo-estra-1,3,5(10)-trien-17-one (64945-54-6)

Conditions	Yield
With sodium hydroxide anschliessendes Ansaeuern;

Upstream product

• 5128-18-7 3-acetoxy-17a-oxa-D-homo-estra-1,3,5⁽¹⁰⁾-trien-17-one 
• 53-16-7 Estrone 
• 901-93-9 estrone acetate 

Relevant academic research and scientific papers

Baeyer-villiger oxidation and oxidative cascade reactions with aqueous hydrogen peroxide catalyzed by lipophilic Li[B(C6F5) 4] and Ca[B(C6F5)4]2

Efficient and selective: Two lipophilic catalysts were used for Baeyer-Villiger (BV) oxidations to give lactones in high yields (see scheme). Cascade reactions involving this BV oxidation were used to selectively obtain either unsaturated carboxylic acids or hydroxylactones in high yields from β-silyl cyclohexanones. Copyright

Steroid 3-O-sulphamate derivatives as inhibitors of oestrone sulphatase

A sulphamate compound suitable for use as an inhibitor of oestrone sulphatase (E.C.3.1.6.2) is described. The compound is a polycyclic compound comprising at least two ring components, wherein the polycyclic compound comprises at least one sulphamate group attached to at least one of the ring components, and wherein at least one of the ring components of the polycyclic structure is a heterocyclic ring.