483-26-1

Basic information

• Product Name: Alloyohimban
• Synonyms: (-)-Alloyohimban;(20α)-Yohimban;Alloyohimban
• CAS NO: 483-26-1
• Molecular Formula: C19H24N2
• Molecular Weight: 280.41
• Mol File: 483-26-1.mol

Chemical Properties

• Boiling Point: 454.1°C at 760 mmHg
• Flash Point: 228.4°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.95E-08mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: Alloyohimban(CAS DataBase Reference)
• NIST Chemistry Reference: Alloyohimban(483-26-1)
• EPA Substance Registry System: Alloyohimban(483-26-1)

Safety Data

• Hazardous Substances Data: 483-26-1(Hazardous Substances Data)

Usage

Chemical compound

Alloyohimban

Primary use

Production of high-strength alloys and manufacturing of stainless steel

Composition

Iron, chromium, and nickel

Properties

Corrosion-resistant

Use in aerospace industry

Ability to withstand high temperatures and pressure, used in aircraft components and turbine blades

Use in automotive industry

Durability, resistance to rust and corrosion, used in car parts and steel structures

Overall importance

Vital role in various industries due to strength, durability, and resistance to corrosion.

InChI:InChI=1/C19H24N2/c1-2-6-14-12-21-10-9-16-15-7-3-4-8-17(15)20-19(16)18(21)11-13(14)5-1/h3-4,7-8,13-14,18,20H,1-2,5-6,9-12H2/t13-,14-,18-/m1/s1

Upstream product

• 69349-93-5 (+/-)-alloyahimbane 
• 69285-18-3 (4aS,14aS)-2,3,4,4a,7,8,13,13b,14,14a-Decahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-5-one 
• 6247-13-8 (S)-2,3,4,4a,7,8,13,14a-Octahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-5-one 
• 259670-57-0 (1S,6S)-4-oxabicyclo[4.4.0]decan-3-one 
• 28755-03-5 3-chloroacetylindole 
• 24731-17-7 ethyl 2-(2-oxocyclohexyl)acetate 
• 53544-45-9 ethyl (2-methylidenylcyclohexyl)acetate 
• 140192-38-7 (+/-)-(13bS*,14aR*)-5,7,8,13,13b,14,14a-hexahydrobenzindolo<2,3-a>quinolizin-5(1H)-one 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 107-21-1 ethylene glycol 
• 111-46-6 diethylene glycol 
• 47136-65-2 sempervirine 
• 22259-53-6 3-aminomethylindole 

Relevant articles and documents

Rhodium-catalyzed hydrocarbonylation of a homoallylamine via n-h activation and application for synthesis of yohimbane alkaloids

We describe syntheses of n-yohimbane and alloyohimbane using Rh-catalyzed hydrocarbonylation, which provides a practical methodology to synthesize a δ-lactam from a secondary homoallyl amine. We have also observed an unexpected transformation where the am

A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids

We report a concise, enantioselective synthesis of the yohimbine alkaloids (-)-rauwolscine and (-)-alloyohimbane. The key transformation involves a highly enantio- and diastereoselective NHC-catalyzed dimerization and an amidation/N-acyliminium ion cyclization sequence to furnish four of the five requisite rings and three of the five stereocenters in two operations. This route also provides efficient access to all four diastereomeric arrangements of the core stereotriad of the yohimbine alkaloids from a common intermediate. This platform approach in combination with the ability to access both enantiomers from the carbene-catalyzed reaction is a powerful strategy that can produce a wide range of complex alkaloids and related structures for future biomedical investigations.

Enantioselective Syntheses of (–)-Alloyohimbane and (–)-Yohimbane by an Efficient Enzymatic Desymmetrization Process

Enantioselective syntheses of (–)-alloyohimbane and (–)-yohimbane were accomplished in a convergent manner. The key step involves a modified mild protocol for the enantioselective enzymatic desymmetrization of a meso-diacetate. This provides convenient access to an optically active monoacetate in multi-gram quantities and in high enantiomeric purity. This monoacetate was converted to (–)-alloyohimbane. Reductive amination of the derived aldehyde caused isomerization to the trans-product and, ultimately, the formation of (–)-yohimbane.

Application of oxidative desymmetrization of meso-tetrahydrofurans: Syntheses of functionalized chiral building blocks and of (-)-alloyohimbane

Oxidative desymmetrization of oxygen functionalized mesotetrahydrofurans was successfully achieved (up to 87% ee) through (salen)manganese(III) catalyzed enantiotopic selective C-H oxidation. The enantioselective synthesis of (-)-alloyohimbane (12) has also been achieved in a short step by using oxidative desymmetrization of meso-tetrahydrofuran as the key step.

Stereoselective Additions of Chiral α-Sulfinyl Ketimine Anions to Ene Esters. Asymmetric Syntheses of Indoloquinolizidine and Yohimban Alkaloids

The in-situ 1,4-addition/ring-closure reactions of chiral α-sulfinyl ketimine anions with acyclic and cyclic ene esters offer a simple, convenient route for the construction of chiral cyclic alkaloids having a nitrogen-atom ring juncture.Asymmetric induction in the conjugate-addition reaction of the carbanions derived from α-sulfinyl ketimines possessing chiral sulfur with various cyclic and acyclic ene esters, subsequent ring-closure reaction, and reduction of the resulting β-sulfinyl enamides were utilized in the syntheses of (-)-1,2,3,4,6,7,12,12b-octahydroindoloquinolizine , (-)-alloyohimban , (+)-3-epi-alloyohimban , and (-)-yohimban .

Stereoselective Addition Reactions of Chiral α-Sulfinyl Ketimine Anions with Ene Esters. Facile Asymmetric Syntheses of Indoloquinolizidine and Yohimbanoid Alkaloids

A convenient route for the construction of chiral indolizidines and yohimbanoid alkaloids from the 1,4-addition/ring-closure reactions of α-sulfinyl ketimine anions with ene esters is presented.