• Name

  indicine-N-oxide

• EINECS
• CAS No. 41708-76-3
• Article Data4
• CAS DataBase
• Density g/cm³
• Solubility
• Melting Point 130.5°C (rough estimate)
• Formula C₁₅H₂₅NO₆
• Boiling Point °Cat760mmHg
• Molecular Weight 315.367
• Flash Point °C
• Transport Information
• Appearance
• Safety Moderately toxic by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of NO_x. See also ESTERS.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Indicine N-oxide;
• PSA 116.42000
• LogP -0.35590

Synthetic route

480-82-0

(+)-indicine

41708-76-3

(+)-indicine N-oxide

Conditions

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;

23944-50-5

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

41708-76-3

(+)-indicine N-oxide

Conditions

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

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

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

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

41708-76-3

(+)-indicine N-oxide

Conditions

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

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

41708-76-3

(+)-indicine N-oxide

Conditions

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

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

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

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

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

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

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

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

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

480-85-3

retronecine

41708-76-3

(+)-indicine N-oxide

Conditions

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

23944-47-0

(+/-)-trachelanthic acid

41708-76-3

(+)-indicine N-oxide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: conc. aq. HCl / 1.5 h / 25 °C 3: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h 4: 0.6 N aq. HCl / 24 h / 25 °C 5: m-chloroperbenzoic acid / CHCl3 / 0.33 h / Ambient temperature View Scheme

94773-28-1

trans-α-isopropylcrotonic acid

41708-76-3

(+)-indicine N-oxide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 85 percent / OsO4, HClO3 3: conc. aq. HCl / 1.5 h / 25 °C 4: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h 5: 0.6 N aq. HCl / 24 h / 25 °C 6: m-chloroperbenzoic acid / CHCl3 / 0.33 h / Ambient temperature View Scheme

95363-32-9

(4R,5S)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

41708-76-3

(+)-indicine N-oxide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.6 N aq. HCl / 24 h / 25 °C 2: m-chloroperbenzoic acid / CHCl3 / 0.33 h / Ambient temperature View Scheme

Indicine-N-oxide Chemical Properties

Indicine-N-oxide Toxicity Data With Reference

Indicine-N-oxide Safety Profile