Leelamine

Base Information

• Chemical Name: Leelamine
• CAS No.: 1446-61-3
• Molecular Formula: C20H31N
• Molecular Weight: 285.473
• Hs Code.: 29214990
• European Community (EC) Number: 215-899-7
• Wikipedia: Leelamine
• Wikidata: Q27181622
• ChEMBL ID: CHEMBL3040626
• Mol file: 1446-61-3.mol

Synonyms:dehydroabietylamine;leelamine

Chemical Property of Leelamine

Chemical Property:

• Appearance/Colour: clear yellow viscous liquid
• Vapor Pressure: 4.59E-06mmHg at 25°C
• Melting Point: 44.50℃
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 382.85 °C at 760 mmHg
• PKA: 10.13±0.29(Predicted)
• Flash Point: 156.732 °C
• PSA: 26.02000
• Density: 0.964 g/cm³
• LogP: 5.47930
• Storage Temp.: Desiccate at +4°C
• Solubility.: Chloroform, DMSO, Methanol
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 285.245649993
• Heavy Atom Count: 21
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

Dehydroabietylamine,tech. ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Rosin and Derivatives
• Canonical SMILES: CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)CN)C
• Isomeric SMILES: CC(C)C1=CC2=C(C=C1)[C@]3(CCC[C@@](C3CC2)(C)CN)C
• Uses: Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.

Technology Process of Leelamine

There total 12 articles about Leelamine 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:

(+)-dehydroabietylamine acetate (2026-24-6) → leelamine (1446-61-3,104530-67-8,1416-08-6,24564-18-9,27174-94-3,66989-22-8,87926-74-7,25512-83-8)

Guidance literature:

With sodium hydroxide; In water; Heating;

DOI:10.1071/CH16545

Reference yield:

C28H35N3O2 → leelamine (1446-61-3,104530-67-8,1416-08-6,24564-18-9,27174-94-3,66989-22-8,87926-74-7,25512-83-8)

Guidance literature:

With hydrazine hydrate; In ethanol; for 3h; Reflux; Inert atmosphere;

Reference yield:

(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxamide (35928-32-6) → leelamine (1446-61-3,104530-67-8,1416-08-6,24564-18-9,27174-94-3,66989-22-8,87926-74-7,25512-83-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/acs.jafc.0c00562

upstream raw materials:

(+)-dehydroabietylnitrile

N-Dehydroabietyl-p-toluenesulfonamide

dehydroabietic acid

(+)-dehydroabietylamine acetate

Downstream raw materials:

bisdehydroabietylamino-N¹,N²-ethane-1,2-diamine

C-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methylamine; compound with (4-tert-butyl-cyclohexylidene)-acetic acid

3-((1,4a-dimethyl-7-(1-methylethyl)-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthrenyl)methylamino)-1-(4-fluorophenyl)-1-propanone

{3-[2-(4-Fluoro-phenyl)-5,5-dimethyl-[1,3]dioxan-2-yl]-propyl}-((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-ylmethyl)-amine

Refernces

Asymmetric reduction with 5-deazaflavin. II. Synthesis of some chiral 5-deazaflavin derivatives

10.1248/cpb.38.312

The research focuses on the development of functional biomimetic coenzyme models, specifically the synthesis of chiral 5-deazaflavin derivatives. The purpose of this study was to prepare new types of chiral deazaflavin derivatives that could effectively discriminate the enantiotopic faces of carbonyls in asymmetric reduction reactions, potentially serving as models for enzymatic systems. The researchers synthesized 5-deazaflavin derivatives with chiral substituents at the C(6) position and a chiral tertiary asymmetric carbon center at C(5). They used various chemicals in the process, including 8-chloro derivative, chiral primary amines such as (+)-dehydroabietylamine and (S)-(-)-phenylethylamine, dicyclohexylcarbodimide (DCC), and N-(tert-butoxycarbonyl)-L-valine.

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