Supinine

Base Information

• Chemical Name: Supinine
• CAS No.: 551-58-6
• Molecular Formula: C₁₅H₂₅NO₄
• Molecular Weight: 283.368
• UNII: W11Q632E7K
• DSSTox Substance ID: DTXSID70203622
• Nikkaji Number: J4.482B
• Wikidata: Q27108360
• Metabolomics Workbench ID: 68096
• Mol file: 551-58-6.mol

Synonyms:spinin

Chemical Property of Supinine

Chemical Property:

• Vapor Pressure: 1.09E-08mmHg at 25°C
• Melting Point: 148.5°C
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 416.8°Cat760mmHg
• PKA: 12.59±0.29(Predicted)
• Flash Point: 205.9°C
• PSA: 70.00000
• Density: 1.18g/cm³
• LogP: 0.63980
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 283.17835828
• Heavy Atom Count: 20
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Supinine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C)O)(C(=O)OCC1=CCN2C1CCC2)O
• Isomeric SMILES: C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O
• Description: A pyrrolizidine alkaloid obtained from Heliotropiurn supinurn, the base forms colourless needles when crystallized from Me2CO. It has [α]D - 23.8° (EtOH) and on alkaline hydrolysis furnishes trachelantic acid and supinidine. The latter has b.p. 158-9°C/1O mm; [α]D - 9.45° (EtOH) and gives a crystalline picrate, m.p.142-3°C.
• Uses: Supinine is a hepatotoxic alkaloid that is excreted through urine as a metabolic pyrrole.

Technology Process of Supinine

There total 13 articles about Supinine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 37.0%

(4S,5S)-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-isopropyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (1369385-54-5) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

(4S,5S)-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-isopropyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate; With trifluoroacetic acid; In water; at 20 ℃; for 1.5h; Inert atmosphere;

In 1,2-dichloro-ethane; at 20 ℃; for 16h;

In dichloromethane; for 12h;

DOI:10.1021/ol300466a

Reference yield:

(S)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide (1369385-45-4) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / -20 °C

1.2: 1 h / -20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5.2: 1.5 h / 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / water / 1.5 h / 20 °C / Inert atmosphere

6.2: MP-BH(OAc)3 / 16 h / 20 °C

6.3: PS-carbonate / 12 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol300466a

Reference yield:

(S)-N-allyl-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide (1369385-47-6) → Amabiline (551-58-6,17958-39-3,17958-43-9,84471-36-3,85798-06-7,92593-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4.2: 1.5 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / water / 1.5 h / 20 °C / Inert atmosphere

5.2: MP-BH(OAc)3 / 16 h / 20 °C

5.3: PS-carbonate / 12 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol300466a

upstream raw materials:

(S)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide

(S)-N-allyl-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide

(S)-2-(2-(1,3-dioxan-2-yl)ethyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-((S)-tertbutylsulfinyl)-2,5-dihydro-1H-pyrrole

((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methanol

Refernces