2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid supplier

Name
3-hydroxy- α-oxoadamantane-1-acetic acid
EINECS 615-199-5
CAS No. 709031-28-7
Article Data12
CAS DataBase
Density 1.477 g/cm³
Solubility
Melting Point 164-165 °C
Formula C₁₂H₁₆O₄
Boiling Point 366.525 °C at 760 mmHg
Molecular Weight 224.257
Flash Point 189.652 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Hydroxy-alpha-oxotricyclo[3.3.1.13,7]decane-1-acetic acid;
PSA 74.60000
LogP 0.97140

Synthetic route

: 709031-35-6
dichloro-(3-hydroxy-adamantan-1-yl)-acetic acid methyl ester

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Stage #1: dichloro-(3-hydroxy-adamantan-1-yl)-acetic acid methyl ester With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16.7h; Stage #2: With hydrogenchloride; sodium hydrogencarbonate In tetrahydrofuran; water for 5h; pH=7.4; Heating;	99.53%
Stage #1: dichloro-(3-hydroxy-adamantan-1-yl)-acetic acid methyl ester With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h; pH=13.24; Stage #2: With hydrogenchloride; sodium hydrogencarbonate In tetrahydrofuran; water at 4 - 20℃; for 101.76h; pH=1.4 - 1.77;	86.6%

: dichloro-(3-hydroxy-adamantan-1-yl)-acetic

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Stage #1: dichloro-(3-hydroxy-adamantan-1-yl)-acetic With sodium hydroxide; sodium hydrogencarbonate In water at 80℃; for 6h; pH=7.22; Stage #2: With hydrogenchloride In water pH=0.15;	99%

: 39917-38-9
1-hydroxy-3-acetyladamantane

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In tert-butyl alcohol at 40℃; for 5h; Reagent/catalyst;	91.8%
With potassium permanganate; potassium hydroxide In tert-butyl alcohol at 40℃; for 5h;	90%
With potassium permanganate; potassium hydroxide In water; tert-butyl alcohol at 35 - 45℃; for 4.5h;	86.6%

: 3-hydroxy-α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid methyl ester

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Stage #1: 3-hydroxy-α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid methyl ester With sodium hydroxide; water In tetrahydrofuran at 5 - 30℃; for 0.5h; pH=7 - 14; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate pH=0.7;	85%
With sodium hydroxide In tetrahydrofuran; water at 30℃; pH=Ca. 7 - 14; Cooling with ice;

: 1660-04-4
1-acetyladamantane

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With potassium permanganate; potassium hydroxide In water at 90℃;	84%
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 60 - 80℃; for 14.5h;	47%
Stage #1: 1-acetyladamantane With sodium hydroxide; potassium permanganate In water at 27 - 55℃; for 24.5 - 25.5h; Stage #2: In water Product distribution / selectivity; Acidic aqueous solution;

: 1660-04-4
1-acetyladamantane

A: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

B: 16091-98-8
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

Conditions

Conditions	Yield
With potassium permanganate; potassium hydroxide In water at 50 - 80℃; for 12h;	A 80% B 0.8 g
With sodium hydroxide; potassium permanganate In water; tert-butyl alcohol at 50 - 65℃; for 35h; Product distribution / selectivity;

: 16091-98-8
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Stage #1: oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid With sulfuric acid; nitric acid Stage #2: With hydrogenchloride In water	76%
Stage #1: oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid With sodium hydroxide; potassium permanganate In water at 20 - 60℃; for 11h; Stage #2: Acidic aqueous solution;
With sodium hydroxide; potassium permanganate In water at 55 - 60℃; for 11h; Product distribution / selectivity;

: 3-hydroxy-1-adamantyl-glycine

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With ω-transaminase

: 828-51-3
1-Adamantanecarboxylic acid

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 25 °C 1.2: 2 h / 25 °C 2.1: tetrahydrofuran / 10 - 20 °C / Inert atmosphere 3.1: potassium permanganate; potassium hydroxide / water / 90 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium permanganate; potassium hydroxide / water; tert-butyl alcohol / 8.5 h / 45 - 60 °C 2.1: thionyl chloride / 6 h / Reflux 3.1: sodium / Petroleum ether / 20 °C 3.2: 20 °C / Reflux 3.3: 6 h / Reflux 4.1: potassium permanganate; potassium hydroxide / tert-butyl alcohol / 5 h / 40 °C View Scheme

: 828-51-3
1-Adamantanecarboxylic acid

A: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

B: 16091-98-8
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 25 °C 1.2: 2 h / 25 °C 2.1: tetrahydrofuran / 10 - 20 °C / Inert atmosphere 3.1: potassium permanganate; potassium hydroxide / water / 12 h / 50 - 80 °C View Scheme

: 351464-84-1
(3r,5r,7r)-N-methoxy-N-methyladamantane-1-carboxamide

A: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

B: 16091-98-8
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 10 - 20 °C / Inert atmosphere 2: potassium permanganate; potassium hydroxide / water / 12 h / 50 - 80 °C View Scheme

: 143467-20-3
1-acetyl-3-chloroadamantane

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / water / 6 h / Reflux 2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C View Scheme

: 768-90-1
1-Adamantyl bromide

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc(II) chloride / dichloromethane / 20 °C 2.1: sulfuric acid; nitric acid / water / 25 h / 1 °C / Cooling with ice 3.1: sodium hydroxide / water; tetrahydrofuran / 16.7 h / 20 °C 3.2: 5 h / pH 7.4 / Heating View Scheme
Multi-step reaction with 5 steps 1: zinc(II) chloride / dichloromethane / 0.08 h / 20 °C / Large scale 2: acetyl chloride / 2 h / 0 - 25 °C / Inert atmosphere; Large scale 3: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.83 h / -60 °C / Inert atmosphere; Cooling with acetone-dry ice 4: sulfuric acid; nitric acid / water / Cooling with ice 5: sodium hydroxide / water; tetrahydrofuran / 30 °C / pH Ca. 7 - 14 / Cooling with ice View Scheme

Yield

Multi-step reaction with 3 steps
1.1: zinc(II) chloride / dichloromethane / 20 °C
2.1: sulfuric acid; nitric acid / water / 25 h / 1 °C / Cooling with ice
3.1: sodium hydroxide / water; tetrahydrofuran / 16.7 h / 20 °C
3.2: 5 h / pH 7.4 / Heating
View Scheme

Multi-step reaction with 5 steps
1: zinc(II) chloride / dichloromethane / 0.08 h / 20 °C / Large scale
2: acetyl chloride / 2 h / 0 - 25 °C / Inert atmosphere; Large scale
3: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.83 h / -60 °C / Inert atmosphere; Cooling with acetone-dry ice
4: sulfuric acid; nitric acid / water / Cooling with ice
5: sodium hydroxide / water; tetrahydrofuran / 30 °C / pH Ca. 7 - 14 / Cooling with ice
View Scheme

: α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid methyl ester

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / water / Cooling with ice 2: sodium hydroxide / water; tetrahydrofuran / 30 °C / pH Ca. 7 - 14 / Cooling with ice View Scheme

: 709031-34-5
dichloro-(tricyclo[3.3.1.13,7]decan-1-yl)acetic acid methyl ester

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid; nitric acid / water / 25 h / 1 °C / Cooling with ice 2.1: sodium hydroxide / water; tetrahydrofuran / 16.7 h / 20 °C 2.2: 5 h / pH 7.4 / Heating View Scheme

: 128665-98-5
α-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid methyl ester

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.83 h / -60 °C / Inert atmosphere; Cooling with acetone-dry ice 2: sulfuric acid; nitric acid / water / Cooling with ice 3: sodium hydroxide / water; tetrahydrofuran / 30 °C / pH Ca. 7 - 14 / Cooling with ice View Scheme

: 30074-09-0
α-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetyl chloride / 2 h / 0 - 25 °C / Inert atmosphere; Large scale 2: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.83 h / -60 °C / Inert atmosphere; Cooling with acetone-dry ice 3: sulfuric acid; nitric acid / water / Cooling with ice 4: sodium hydroxide / water; tetrahydrofuran / 30 °C / pH Ca. 7 - 14 / Cooling with ice View Scheme

: 3-hydroxy-1-adamantanecarbonyl chloride

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium / Petroleum ether / 20 °C 1.2: 20 °C / Reflux 1.3: 6 h / Reflux 2.1: potassium permanganate; potassium hydroxide / tert-butyl alcohol / 5 h / 40 °C View Scheme

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 6 h / Reflux 2.1: sodium / Petroleum ether / 20 °C 2.2: 20 °C / Reflux 2.3: 6 h / Reflux 3.1: potassium permanganate; potassium hydroxide / tert-butyl alcohol / 5 h / 40 °C View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With NAD; ammonium formate; diothiothreitol In ammonium hydroxide at 40℃; for 38h; pH=8.0; Enzymatic reaction;	100%
With glutamate at 37℃; for 0.5h; pH=8; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;	100%
With 4-aminomethylphenol; Na(1+)*C20H23N2O4S(1-); sodium hydroxide In water at 40℃; for 12h; Reagent/catalyst; Temperature; enantioselective reaction;	98.2%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 64-17-5
ethanol

: 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid ethyl ester

Conditions

Conditions	Yield
With acetyl chloride at 5℃; for 3h; Inert atmosphere; Reflux;	95%
With thionyl chloride at 0 - 5℃; for 1h; Inert atmosphere;	90%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 67-63-0
isopropyl alcohol

: 2-(3-hydroxy-1-adamantyl)-2-oxo acetic acid isopropyl ester

Conditions

Conditions	Yield
With thionyl chloride at 0 - 5℃; for 1h; Inert atmosphere;	95%
With acetyl chloride at 5℃; for 3h; Inert atmosphere; Reflux;	80%

: 67-56-1
methanol

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 3-hydroxy-α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid methyl ester

Conditions

Conditions	Yield
With acetyl chloride at 5℃; for 3h; Inert atmosphere; Reflux;	93%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 2-(3-hydroxy-1-adamantyl)-2-hydroxyiminoacetic acid

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In water at 0 - 5℃; for 2h; pH=7;	90%
With hydroxylamine hydrochloride; sodium hydroxide In water for 4h; Cooling with ice;	90%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 3-hydroxy-1-adamantyl-glycine

Conditions

Conditions	Yield
With ammonium formate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In methanol at 50℃; for 24h; Inert atmosphere;	86%
With α-transaminase

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 78-83-1
2-methyl-propan-1-ol

: C16H24O4

Conditions

Conditions	Yield
With thionyl chloride at 0 - 5℃; for 1h;	80%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 115-11-7
isobutene

: tert-butyl 2-(3-hydroxy-1-adamantyl)-2-oxoacetate

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane; dichloromethane at -30 - 20℃; for 20h; Sealed tube; High pressure;	75%

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: 618-36-0
rac-methylbenzylamine

A: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

B: 98-86-2
acetophenone

Conditions

Conditions	Yield
With L-2-aminobutyric acid; pyridoxal 5'-phosphate; (S)-selective ω-transaminase from Paracoccus denitrificans; branched-chain aminoacid transaminase In aq. phosphate buffer; hexane at 37℃; for 61h; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	A 62% B n/a

...Expand

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

: (1S,3S,5S)-2-(2-(3-hydroxyadamantan-1-yl)-2-oxoacetyl)-2-azabicyclo[3.1.0]hexan-3-carboxamide

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In acetonitrile at -5 - 15℃; for 1.5h;	4.38 g

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-(2-(3-hydroxyadamantan-1-yl)-2-(hydroxyimino)acetyl)-2-azabicyclo[3.1.0]hexan-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C 2: hydroxylamine hydrochloride; sodium acetate / water; methanol / 23 h / 40 °C View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-(2-(3-hydroxyadamantan-1-yl)-2-(hydroxyimino)acetyl)-2-azabicyclo[3.1.0]hexan-3-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C 2.1: 3-pyridinecarboxylic acid ethyl ester; trifluoroacetic anhydride / ethyl acetate / 1 h / 0 °C 2.2: 10 - 15 °C 3.1: hydroxylamine hydrochloride / water; methanol / 40 °C View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-((S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo[3.1.0]hexan-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C 2: hydroxylamine hydrochloride; sodium acetate / water; methanol / 23 h / 40 °C 3: hydrogen / methanol View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: saxagliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C 2.1: 3-pyridinecarboxylic acid ethyl ester; trifluoroacetic anhydride / ethyl acetate / 1 h / 0 °C 2.2: 10 - 15 °C 3.1: pyridoxamine dihydrochloride; potassium carbonate; cinchonidine / water; methanol / 48 h / 50 °C View Scheme
Multi-step reaction with 6 steps 1.1: pyrographite / water / 0.08 h / pH Ca. 8 / Large scale 1.2: 42 h / 40 °C / pH 7.5 - 8 / Large scale 2.1: sodium hydroxide / Isopropyl acetate / 4 h / 20 °C / pH 10 / Large scale 3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice 3.2: 20 °C 4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 4.2: 7.55 h / Cooling 5.1: dichloromethane / methanol / 20 °C / Inert atmosphere 6.1: water; dichloromethane View Scheme

Yield

Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C
2.1: 3-pyridinecarboxylic acid ethyl ester; trifluoroacetic anhydride / ethyl acetate / 1 h / 0 °C
2.2: 10 - 15 °C
3.1: pyridoxamine dihydrochloride; potassium carbonate; cinchonidine / water; methanol / 48 h / 50 °C
View Scheme

Multi-step reaction with 6 steps
1.1: pyrographite / water / 0.08 h / pH Ca. 8 / Large scale
1.2: 42 h / 40 °C / pH 7.5 - 8 / Large scale
2.1: sodium hydroxide / Isopropyl acetate / 4 h / 20 °C / pH 10 / Large scale
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
4.2: 7.55 h / Cooling
5.1: dichloromethane / methanol / 20 °C / Inert atmosphere
6.1: water; dichloromethane
View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-(2-(3-hydroxyadamantan-1-yl)-2-oxoacetyl)-2-azabicyclo[3.1.0]hexan-3-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 1.5 h / -5 - 15 °C 2.1: 3-pyridinecarboxylic acid ethyl ester; trifluoroacetic anhydride / ethyl acetate / 1 h / 0 °C 2.2: 10 - 15 °C View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: C13H21NO3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetyl chloride / 3 h / 5 °C / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; ammonium formate / ethanol / 40 °C / 4560.31 Torr / Inert atmosphere View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: C14H23NO3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetyl chloride / 3 h / 5 °C / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; ammonium formate / ethanol / 40 °C / 4560.31 Torr / Inert atmosphere View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: isopropyl 2-amino-2-(3-hydroxy-1-adamantyl)acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetyl chloride / 3 h / 5 °C / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; ammonium formate / ethanol / 40 °C / 4560.31 Torr / Inert atmosphere View Scheme

: 709031-28-7
3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid

: C16H27NO3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 1,4-dioxane; dichloromethane / 20 h / -30 - 20 °C / Sealed tube; High pressure 2: palladium 10% on activated carbon; ammonium formate / ethanol / 40 °C / 4560.31 Torr / Inert atmosphere View Scheme

2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid Specification

The cas register number of 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid is 709031-28-7. It also can be called as 3-Hydroxy-alpha-oxotricyclo[3.3.1.13,7]decane-1-acetic acid and the Systematic name about this chemical is (3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)(oxo)acetic acid.

Physical properties about 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid are: (1)ACD/LogP: -0.23; (2)ACD/LogD (pH 5.5): -3; (3)ACD/LogD (pH 7.4): -4; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 74.6 Å²; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 54.384 cm³; (14)Molar Volume: 151.827 cm³; (15)Polarizability: 21.56x0^-24cm³; (16)Surface Tension: 80.666 dyne/cm; (17)Enthalpy of Vaporization: 70.936 kJ/mol; (18)Boiling Point: 366.525 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
SMILES: O=C(O)C(=O)C13CC2CC(CC(O)(C1)C2)C3
InChI: InChI=1/C12H16O4/c13-9(10(14)15)11-2-7-1-8(3-11)5-12(16,4-7)6-11/h7-8,16H,1-6H2,(H,14,15)
InChIKey: UDKIRRNUAXWHTO-UHFFFAOYAO
Std. InChI: InChI=1S/C12H16O4/c13-9(10(14)15)11-2-7-1-8(3-11)5-12(16,4-7)6-11/h7-8,16H,1-6H2,(H,14,15)
Std. InChIKey: UDKIRRNUAXWHTO-UHFFFAOYSA-N

Product Name

3-hydroxy- α-oxoadamantane-1-acetic acid

Synthetic route

2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid Specification

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