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(+)-indicine
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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; |
(2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
4(R)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(1'S,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(2R,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
(2S,4R,5S)-2-(t-butyl)-4-isopropyl-5-methyl-1,3-dioxolane-4-carboxylic acid
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
retronecine
(+)-indicine N-oxide
Conditions | Yield |
---|---|
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 |
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:C15H25NO6
Molecular Weight :315.3621
Molecular Structure :
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 (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