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Indicine-N-oxide

  • Name Indicine-N-oxide
  • EINECSN/A
  • CAS No. 41708-76-3
  • Densityg/cm3
  • PSA116.42000
  • LogP-0.35590
  • SolubilityN/A
  • Melting Point130.5°C (rough estimate)
  • FormulaC15H25NO6
  • Boiling Point°Cat760mmHg
  • Molecular Weight315.367
  • Flash Point°C
  • Transport InformationN/A
  • AppearanceN/A
  • SafetyModerately toxic by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 41708-76-3 (indicine-N-oxide)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data4

Indicine-N-oxide Synthetic route

480-82-0

(+)-indicine

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In acetone for 2h; Ambient temperature;81%
With 3-chloro-benzenecarboperoxoic acid In acetone for 2h; Ambient temperature;81%
With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.333333h; Ambient temperature;
With 3-chloro-benzenecarboperoxoic acid In acetone for 1h; Ambient temperature;
23944-50-5

(2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: concd hydrochloric acid / Ambient temperature
2: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h
3: MCPBA / acetone / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: conc. aq. HCl / 1.5 h / 25 °C
2: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h
3: 0.6 N aq. HCl / 24 h / 25 °C
4: m-chloroperbenzoic acid / CHCl3 / 0.33 h / Ambient temperature
View Scheme
95462-07-0

4(R)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h
2: MCPBA / acetone / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h
2: 0.6 N aq. HCl / 24 h / 25 °C
3: m-chloroperbenzoic acid / CHCl3 / 0.33 h / Ambient temperature
View Scheme

(2S,3R,4S)-3-Benzyloxy-3-isopropyl-pentane-1,2,4-triol

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaIO4, KMnO4 / 2-methyl-propan-2-ol; H2O / 1 h / Ambient temperature
2: hydrogen / 10 percent Pd/C / methanol / 3 h / Ambient temperature
3: concd hydrochloric acid / Ambient temperature
4: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h
5: MCPBA / acetone / 1 h / Ambient temperature
View Scheme

(2R,3S)-2-Benzyloxy-3-hydroxy-2-isopropyl-butyric acid

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen / 10 percent Pd/C / methanol / 3 h / Ambient temperature
2: concd hydrochloric acid / Ambient temperature
3: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h
4: MCPBA / acetone / 1 h / Ambient temperature
View Scheme

Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-4-isopropyl-5-methyl-tetrahydro-furan-3-yl ester

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaBH4 / ethanol / 1.) r.t., overnight; 2.) reflux, 20 h
2: NaIO4, KMnO4 / 2-methyl-propan-2-ol; H2O / 1 h / Ambient temperature
3: hydrogen / 10 percent Pd/C / methanol / 3 h / Ambient temperature
4: concd hydrochloric acid / Ambient temperature
5: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h
6: MCPBA / acetone / 1 h / Ambient temperature
View Scheme
132585-75-2

(1'S,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 9.3 percent / camphorsulfonic acid / benzene / 72 h / Heating
2: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 28 h
3: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 62 percent / camphorsulfonic acid / benzene / 72 h / Heating
2: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 22 h
3: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 12 percent / camphorsulphonic acid / benzene / 72 h / Heating
2: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
3: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 77 percent / camphorsulphonic acid / benzene / 72 h / Heating
2: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
3: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme
126453-22-3

(2R,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 28 h
2: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
2: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme
126331-49-5

(2S,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 22 h
2: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
2: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme
480-85-3

retronecine

41708-76-3

(+)-indicine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 28 h
2: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 22 h
2: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
2: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1.) 2.3 eq. DCC, 0.3 eq. DMAP; 2.) 1M HCl / 1.) toluene, rt, 6 days; 2.) rt, 22 h
2: 81 percent / m-CPBA / acetone / 2 h / Ambient temperature
View Scheme

Indicine-N-oxide Chemical Properties

IUPAC Name: (7-Hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl)methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-butanoate
Synonyms of Indicine-N-oxide (CAS NO.41708-76-3) :  Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-4-oxido-1H-pyrrolizin-7-yl)methyl ester ; 2,3-Dihydroxy-2-(1-methylethyl) butanoic acid (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester N-oxide ; Echinatine, N-oxide ; Heliotridine viridiflorate N-oxide
CAS NO: 41708-76-3
Molecular Formula:C15H25NO        
Molecular Weight :315.3621     
Molecular Structure :

Indicine-N-oxide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 1200mg/kg (1200mg/kg)   Government Reports Announcements. Vol. 74(9), Pg. 60, 1974.
mouse LD50 intraperitoneal 1917mg/kg (1917mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 3733mg/kg (3733mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. PB84-161694,

Indicine-N-oxide Safety Profile

 Indicine-N-oxide (CAS NO.41708-76-3) is moderately toxic by intraperitoneal and intravenous routes. When Indicine-N-oxide (CAS NO.41708-76-3) is heated to decomposition, it emits toxic fumes of NOx. See also ESTERS.

RIDADR 1544
HazardClass 6.1(b)
PackingGroup III

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