Magellanine

Base Information

• Chemical Name: Magellanine
• CAS No.: 61273-75-4
• Molecular Formula: C17H25NO2
• Molecular Weight: 275.391
• UNII: BLX5LW8WRA
• DSSTox Substance ID: DTXSID90976765
• Nikkaji Number: J18.335K
• Wikipedia: Magellanine
• Wikidata: Q6730091
• Mol file: 61273-75-4.mol

Synonyms:magellanine

Chemical Property of Magellanine

Chemical Property:

• Vapor Pressure: 3.31E-09mmHg at 25°C
• Boiling Point: 430.2°Cat760mmHg
• Flash Point: 214°C
• PSA: 40.54000
• Density: 1.19g/cm³
• LogP: 1.79840
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 275.188529040
• Heavy Atom Count: 20
• Complexity: 485

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C23CC4CN(CCC4C2C(CC3C1)O)C
• Isomeric SMILES: CC1=CC(=O)[C@]23C[C@@H]4CN(CC[C@@H]4[C@H]2[C@H](C[C@@H]3C1)O)C

Technology Process of Magellanine

There total 37 articles about Magellanine 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: 76.0%

(3R,4aS,6S,6aR,6bS,10aS,11aS)-6-hydroxy-3,9-dimethyltetradecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one → (-)-magellanine (61273-75-4)

Guidance literature:

(3R,4aS,6S,6aR,6bS,10aS,11aS)-6-hydroxy-3,9-dimethyltetradecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one; With chloro-trimethyl-silane; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

With N-(tert-butyl)benzenesulfinimidoyl chloride; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 6h; Further stages; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01975

Reference yield:

(+)-magellaninone (73885-47-9) → (-)-magellanine (61273-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / NaBH₄ / ethanol

2: 1.) Ph₃P, diethyl azodicarboxylate (DEAD), HCOOH, 2.) 10percent aq. KOH / 1.) THF, 2.) CH₃OH

With potassium hydroxide; sodium tetrahydroborate; formic acid; triphenylphosphine; diethylazodicarboxylate; In ethanol;

DOI:10.1021/ja00063a072

Reference yield:

(1S,3aR,4S,5aS,7R,9aS)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,4,5,5a,6,7-octahydro-1H-cyclopenta[c]indene-4,7-diol → (-)-magellanine (61273-75-4)

Guidance literature:

Multi-step reaction with 18 steps

1: (i-Pr)2NEt / CH₂Cl₂

2: Bu₄NF, 3-A sieves / hexamethylphosphoric acid triamide / Ambient temperature

3: pyridinium chlorochromate (PCC)/Al₂O₃ / CH₂Cl₂

4: LiN(SiMe₃)2 / tetrahydrofuran

5: H₂O₂, pyridine

6: 2.) KF, 3.) lithium diisopropylamide (LDA)

7: NaBH₄ / methanol / Ambient temperature

8: 2.) tris(trimethylsilyl)silane, AIBN / 2.) benzene

9: NaBH₄, CoCl₂ / methanol

10: KOH / methanol

11: NaH / tetrahydrofuran

12: LDA / tetrahydrofuran / -78 - -10 °C

13: aq. HCl / tetrahydrofuran

14: MnO₂ / CHCl₃

15: tetrahydrofuran / -78 °C

16: 1.) LiAlH₄, 2.) Cr₂O₃, aq. H₂SO₄ / 1.) THF, reflux

17: 76 percent / NaBH₄ / ethanol

18: 1.) Ph₃P, diethyl azodicarboxylate (DEAD), HCOOH, 2.) 10percent aq. KOH / 1.) THF, 2.) CH₃OH

With pyridine; hydrogenchloride; manganese(IV) oxide; aluminum oxide; chromium(III) oxide; potassium fluoride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; 3 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform;

DOI:10.1021/ja00063a072

upstream raw materials:

C⁽⁵⁾-epimagellanine

(+)-magellaninone

Downstream raw materials:

(4aR)-2c,3c-epoxy-6c-hydroxy-3t,9-dimethyl-(4ar,6at,6bc,10ac,11atC¹)-tetradecahydro-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one

(+)-magellaninone

Refernces

• 1、 Kozaka, Takashi,Miyakoshi, Naoki,Mukai, Chisato. "Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions". . p. 10147 - 10154. Retrieved 2007.
• 2、 Hirst,Johnson Jr.,Overman. "First total synthesis of Lycopodium alkaloids of the magellanane group. Enantioselective total syntheses of (-)-magellanine and (+)-magellaninone". . p. 2992 - 2993. Retrieved 2007/10/02.