Lythrine

Base Information

• Chemical Name: Lythrine
• CAS No.: 5286-10-2
• Molecular Formula: C₂₆H₂₉NO₅
• Molecular Weight: 435.52
• UNII: S16X2W9YAB
• Nikkaji Number: J598.494G
• Wikidata: Q27893782
• Mol file: 5286-10-2.mol

Synonyms:cryogenine;cryogenine, (10alpha)-isomer;vertine;lythrine

Chemical Property of Lythrine

Chemical Property:

• Boiling Point: 655.4°Cat760mmHg
• Flash Point: 350.2°C
• PSA: 68.23000
• Density: 1.3g/cm³
• LogP: 4.64230
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 435.20457303
• Heavy Atom Count: 32
• Complexity: 698

Purity/Quality:

99%, ^*data from raw suppliers

Lythrine ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C3CC(CC4N3CCCC4)OC(=O)C=CC5=CC2=C(C=C5)O)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)[C@@H]3C[C@H](C[C@H]4N3CCCC4)OC(=O)/C=C\C5=CC2=C(C=C5)O)OC
• Description: This alkaloid is also present in Heimia salicifolia Link & Otto and is obtained as long, glistening needles from either CH2Clr light petroleum or CH2Cl2-MeOH. It is dextrorotatory with [α]25D + 40.6° (c 0.3, CHC13) and the ultraviolet spectrum shows two absorption maxima at 260 and 284 mJ.1. The following salts and derivatives have been prepared to characterize the base: the hydrochloride as prisms, m.p. 325-331 °c (dec.); the acetyl derivative, m.p. In-3°C; [o:lf,S + 33.1 ° (c 0.75, CHC13) and the methyl ether, m.p. 239-24loC; the latter yielding a crystalline hydrochloride and hydrobromide containing MeOH of crystalliza_x0002_tion. Lythrine is an alkaloid originally isolated from H. salicifolia that inhibits prostaglandin synthetase (IC50 = 469 μM).

Technology Process of Lythrine

There total 44 articles about Lythrine 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:

C32H43NO5Si → (+)-vertine (5286-10-2,57572-82-4,57572-83-5,10308-13-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -30 ℃; for 1h;

DOI:10.1039/c2ob25880c

Reference yield:

2(RS)-(2-hydroxyethyl)piperidine (1484-84-0) → (+)-vertine (5286-10-2,57572-82-4,57572-83-5,10308-13-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: ethanol / Resolution of racemate; Cooling

2.1: triethylamine / dichloromethane / 20 °C

3.1: phosgene; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 4.5 h / -78 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

6.1: sodium hydroxide / methanol / 16 h / 55 °C

7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

8.1: sodium hydroxide / tetrahydrofuran / 4 h / 0 - 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / 1,2-dimethoxyethane / 18 h / 95 °C / Inert atmosphere

10.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

11.1: manganese(IV) oxide / diethyl ether; acetone / 0.33 h

12.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

13.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

14.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

15.1: nysted reagent; titanium tetrachloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

16.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 16 h / 110 °C / Inert atmosphere

17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -30 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; phosgene; dmap; manganese(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nysted reagent; tetrabutyl ammonium fluoride; titanium tetrachloride; L-Selectride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; cesium fluoride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; acetone; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1039/c2ob25880c

Reference yield:

(+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester (1202039-12-0) → (+)-vertine (5286-10-2,57572-82-4,57572-83-5,10308-13-1)

Guidance literature:

Multi-step reaction with 12 steps

1: sodium hydroxide / methanol / 16 h / 55 °C

2: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

3: sodium hydroxide / tetrahydrofuran / 4 h / 0 - 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / 1,2-dimethoxyethane / 18 h / 95 °C / Inert atmosphere

5: L-Selectride / tetrahydrofuran / 1 h / -78 °C

6: manganese(IV) oxide / diethyl ether; acetone / 0.33 h

7: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

8: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

9: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

10: nysted reagent; titanium tetrachloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

11: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 16 h / 110 °C / Inert atmosphere

12: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -30 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; manganese(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nysted reagent; tetrabutyl ammonium fluoride; titanium tetrachloride; L-Selectride; triethylamine; cesium fluoride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1039/c2ob25880c

upstream raw materials:

diazomethane

Demethylvertine

2(RS)-(2-hydroxyethyl)piperidine

(+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester

Downstream raw materials:

17,22,23-trimethoxylythran-11-one

12,13-dihydro-17-hydroxy-13(S),22,23-trimethoxylythran-11-one

dihydro-13(S),17,22,23-tetramethoxylythran-11-one

12,13-dihydro-17,22,23-trimethoxy.13(S)-hydroxylythran-11-one

Refernces

• 1、 Chausset-Boissarie, La?titia,àrvai, Roman,Cumming, Graham R.,Guénée, Laure,Kündig, E. Peter. "Asymmetric synthesis of (+)-vertine and (+)-lythrine". . p. 6473 - 6479. Retrieved 2012/09/08.