Lycopodine

Base Information

• Chemical Name: Lycopodine
• CAS No.: 466-61-5
• Molecular Formula: C16H25NO
• Molecular Weight: 247.3758
• Hs Code.: 2933990090
• UNII: 2P5MU968XW,NTV9A2GW9H
• DSSTox Substance ID: DTXSID201032264
• Wikidata: Q27107261
• Metabolomics Workbench ID: 53270
• ChEMBL ID: CHEMBL3805710
• Mol file: 466-61-5.mol

Synonyms:(16R)-methyllycopodan-5-one;lycopodine

Chemical Property of Lycopodine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 114-115°; mp (racemate) 130-131°
• Boiling Point: 373.5°Cat760mmHg
• PKA: 9.36±0.40(Predicted)
• Flash Point: 137.2°C
• PSA: 20.31000
• Density: 1.1g/cm³
• LogP: 2.94810
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 247.193614421
• Heavy Atom Count: 18
• Complexity: 379

Purity/Quality:

99%, ^*data from raw suppliers

LYCOPODINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2CC(=O)C3CCCN4C3(C1)C2CCC4
• Isomeric SMILES: C[C@@H]1C[C@H]2CC(=O)[C@H]3CCCN4[C@]3(C1)[C@@H]2CCC4
• Description: This alkaloid has, so far, been discovered in all Lycopodium species with the exception of L. saururus Lam. It was first obtained by B6deker who assigned to it the formula C32Hs203N2, altered to that given by Achmatowicz and Uzieblo and confirmed by Manske and Marion. It forms colourless prisms from Et20 and has [α]20D - 9.01 ° (Me2CO). It yields crystalline salts and derivatives: the perchlorate, m.p. 276°C; methochloride, m.p. 238-240°C, methiodide, m.p. 335- 7°C and a hydrazone, mop. 20B-2l0°C. According to Bodeker it also yields a crystalline hydrochloride and aurichloride.Even under pressure at 200°C in the presence of Raney Ni, the base cannot be hydrogenated. On selenium dehydrogenation, a complex mixture of bases is formed from which 7 -methylquinoline and 5:7 -dimethylquinoline have been identified. 7 -methylquinoline is also stated to be formed when the base is heated with palladium as catalyst. A stereospecific total synthesis of the (±)-form has been described.

Technology Process of Lycopodine

There total 32 articles about Lycopodine 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: 87.0%

(+/-)-3,4-dehydrolycopodine (69060-89-5) → (+/-)-lycopodin (466-61-5,6883-69-8,18688-24-9,33190-30-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; for 15h; under 760 Torr;

Reference yield: 80.0%

C16H25NO → lycopodine (466-61-5)

Guidance literature:

C₁₆H₂₅NO; With hydrogen bromide; acetic acid; In methanol; at 20 ℃;

With sodium hydroxide; In methanol; water;

DOI:10.1016/j.tetlet.2018.12.007

Reference yield: 67.0%

β-dihydrolycopodine (23768-74-3) → lycopodine (466-61-5)

Guidance literature:

With Jones reagent; In acetone; at 0 ℃; enantioselective reaction;

DOI:10.1021/acs.orglett.6b02072

upstream raw materials:

C₁₆H₂₃NO

pulegone

(5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one

(R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate

Refernces

• 1、 Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong. "Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization". . p. 4328 - 4331. Retrieved 2016/11/09.
• 2、 Yang, Hua,Carter, Rich G.,Zakharov, Lev N.. "Enantioselective total synthesis of lycopodine". supporting information; experimental part. p. 9238 - 9239. Retrieved 2009/02/03.