(-)-Minovine

Base Information

• Chemical Name: (-)-Minovine
• CAS No.: 19074-77-2
• Molecular Formula: C22H28N2O2
• Molecular Weight: 352.46992
• DSSTox Substance ID: DTXSID50940649
• Wikidata: Q105375534
• Mol file: 19074-77-2.mol

Synonyms:(-)-Minovine;DTXSID50940649

Chemical Property of (-)-Minovine

Chemical Property:

• Melting Point: 79-81°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 352.215078140
• Heavy Atom Count: 26
• Complexity: 659

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12CCCN3C1C4(CC3)C5=CC=CC=C5N(C4=C(C2)C(=O)OC)C
• Isomeric SMILES: CC[C@]12CCCN3[C@H]1[C@]4(CC3)C5=CC=CC=C5N(C4=C(C2)C(=O)OC)C
• Description: A further alkaloid isolated from Vinca minor L., this base is possibly optically inactive, the specific rotation reported being [α]D 00 ± 2° (c 1.0, EtOH). The ultraviolet spectrum in EtOH has a broad absorption maximum at 338 mil and an inflexion at 310 mil. The structure has been confirmed by the synthesis of the (±)-form.

Technology Process of (-)-Minovine

There total 40 articles about (-)-Minovine 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: 53.0%

C24H33N3O7S → (+/-)-3-methoxycarbonyl-Δ3,4-1-methylaspermidospermidine + (+/-)-minovine (19074-77-2,19621-72-8)

Guidance literature:

With sodium hydride; In toluene; at 100 ℃; for 1.5h;

DOI:10.1021/ol050017s

Reference yield: 52.0%

methyl 2-(3-(2-(3-ethyl-2-oxopiperidin-1-yl)ethyl)-1-methyl-1H-indol-2-yl)acrylate → (±)-vincaminorine + (+/-)-minovine (19074-77-2,19621-72-8)

Guidance literature:

methyl 2-(3-(2-(3-ethyl-2-oxopiperidin-1-yl)ethyl)-1-methyl-1H-indol-2-yl)acrylate; With bis(triphenylphosphine)carbonyliridium(I) chloride; 1,1,3,3-tetramethyldisilazane; In toluene; at 20 ℃; Inert atmosphere;

With silica gel; In toluene; at 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201605503

Reference yield: 39.0%

C24H33N3O7S → (+/-)-3-(methoxycarbonyl)-Δ3,4-1-methylaspidospermidine + (+/-)-minovine (19074-77-2,19621-72-8)

Guidance literature:

C₂₄H₃₃N₃O₇S; With sodium hydride; In tetrahydrofuran; at 23 ℃; for 0.5h;

In toluene; for 1.5h; Heating;

DOI:10.1021/ja061256t

upstream raw materials:

(±)-vincadifformine

methyl iodide

N¹-methyl-N-(imidazol-1-ylcarbonyl)tryptamine

methyl 5-[(2-(1-methyl-1H-indol-3-yl)ethyl)amino]-1,3,4-oxadiazole-2-carboxylate