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Technology Process of Alloyohimbane

Alloyohimbane

Base Information
  • Chemical Name:Alloyohimbane
  • CAS No.:483-26-1
  • Molecular Formula:C19H24N2
  • Molecular Weight:280.41
  • Hs Code.:
  • NSC Number:127746
  • DSSTox Substance ID:DTXSID50964042
Alloyohimbane

Synonyms:alloyohimbane

Suppliers and Price of Alloyohimbane
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
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Total 5 raw suppliers
Chemical Property of Alloyohimbane
Chemical Property:
  • Vapor Pressure:1.95E-08mmHg at 25°C 
  • Boiling Point:454.1°C at 760 mmHg 
  • Flash Point:228.4°C 
  • PSA：19.03000 
  • Density:1.19g/cm3 
  • LogP:4.21510 
  • XLogP3:4.4
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:0
  • Exact Mass:280.193948774
  • Heavy Atom Count:21
  • Complexity:395
Purity/Quality:

99% *data from raw suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:C1CCC2CN3CCC4=C(C3CC2C1)NC5=CC=CC=C45
  • General Description Alloyohimban (or alloyohimbane) is a yohimbine alkaloid characterized by a cis-fused hexahydroisoquinolone core, synthesized via an intramolecular Diels-Alder reaction of N-acylvinyl imidates, which efficiently constructs the DE ring system central to its structure. Alloyohimban is derived through key intermediates involving deconjugation, cycloaddition, and reduction steps, highlighting its structural complexity and relevance in alkaloid chemistry.
Technology Process of Alloyohimbane

There total 100 articles about Alloyohimbane 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: 92.0%

(-)-alloyohimban-21-one
137119-66-5

(-)-alloyohimban-21-one

(-)-alloyohimbane
483-26-1

(-)-alloyohimbane

Guidance literature:
With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1021/jo00025a011

Reference yield: 92.0%

(-)-dehydroalloyohimbane
96444-10-9

(-)-dehydroalloyohimbane

(-)-alloyohimbane
483-26-1

(-)-alloyohimbane

Guidance literature:
With hydrogen; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1246/cl.1985.71

Reference yield: 83.0%

(4a'S,8a'R)-3-<(3'oxo-2'-decahydroisoquinolinyl)ethyl>indole
121786-14-9

(4a'S,8a'R)-3-<(3'oxo-2'-decahydroisoquinolinyl)ethyl>indole

(-)-alloyohimbane
483-26-1

(-)-alloyohimbane

Guidance literature:
With trichlorophosphate; for 3h; Heating;
DOI:10.3987/com-99-s20
upstream raw materials:

(+/-)-alloyahimbane

1-methyl-4,9-dihydro-3H-β-carboline

1-cyclohexenoyl chloride

(4a'S,8a'R)-3-<(3'oxo-2'-decahydroisoquinolinyl)ethyl>indole

Refernces

Vinyl imidates in cycloaddition reactions: Synthesis of (±)-alloyohimbane

10.1016/S0040-4039(00)01093-5

The study focuses on the synthesis of (+)-alloyohimbane, a yohimbine alkaloid, using the intramolecular Diels-Alder reaction of N-acylvinyl imidates as a key methodology. This approach provides a rapid entry into cis-fused hexahydroisoquinolones, which are essential for constructing the DE rings of yohimbine alkaloids. The chemicals used in the study include sorbic acid, LDA (lithium diisopropylamide), acid chloride, 2-ethoxy-1-aza-1,3-butadiene, benzene, NaBH3CNBH3 (sodium cyanoborohydride), TFA (trifluoroacetic acid), and various other reagents for the synthesis and transformation of intermediates. These chemicals serve to deconjugate sorbic acid, form the Diels-Alder precursor, effect the cycloaddition to form the cycloaddduct, and subsequently reduce and modify the product to afford the target lactam and ultimately (+)-alloyohimbane. The study also developed a radical-based strategy for synthesizing indoline electrophiles from o-bromoaniline derivatives, which are crucial for the synthesis of substituted indolines and the completion of the alkaloid structure.

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