5227-24-7

Basic information

• Product Name: cassine
• Synonyms: cassine;(-)-12-[(2S)-5β-Hydroxy-6β-methylpiperidine-2-yl]dodecane-2-one;Cassine【Alkaloid】
• CAS NO: 5227-24-7
• Molecular Formula: C₁₈H₃₅NO₂
• Molecular Weight: 297.476
• Mol File: 5227-24-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 58 °C
• Boiling Point: 424.8°Cat760mmHg
• Flash Point: 210.7°C
• Appearance: /
• Density: 0.931g/cm³
• Vapor Pressure: 5.39E-09mmHg at 25°C
• Refractive Index: 1.465
• PKA: 14.93±0.60(Predicted)
• CAS DataBase Reference: cassine(CAS DataBase Reference)
• NIST Chemistry Reference: cassine(5227-24-7)
• EPA Substance Registry System: cassine(5227-24-7)

Safety Data

• Hazardous Substances Data: 5227-24-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H35NO2/c1-15(20)11-9-7-5-3-4-6-8-10-12-17-13-14-18(21)16(2)19-17/h16-19,21H,3-14H2,1-2H3/t16-,17+,18-/m1/s1

Upstream product

• 36651-38-4 ethyl 10-oxo-decanecarboxylate 
• 70475-68-2 trans,trans-2,6-octadiene-1,8-diol 
• 57689-15-3 16-hydroxy-17-nitro-octadecane-2,13-dione 
• 494825-64-8 (2R,3R,6R,2'Z)-2-methyl-N-tert-butoxycarbonyl-3-methoxymethoxy-6-(2',11'-dodecadienyl)piperidine 
• 494825-65-9 (2R,3R,6R,2'Z)-2-methyl-N-tert-butoxycarbonyl-3-methoxymethoxy-6-(11'-oxo-2'-dodecenyl)piperidine 
• 880871-88-5 (4R,5R)-4-acetoxy-5-azido-hexanal 
• 880871-96-5 C₂₂H₃₇NO₅ 
• 880871-95-4 (2R,3R)-2-methyl-6-[10'-(2'-methyl-[1,3]-dioxolan-2-yl)-2'-oxo-decyliden]-piperidin-3-yl acetate 
• 880871-94-3 diethyl [10'-(2'-methyl-[1,3]-dioxolan-2-yl)-2'-oxo-decyl]phosphonate 
• 944055-78-1 ethyl 9-(2-methyl-([1,3]-dioxolan-2-yl))-nonanoate 
• 945011-77-8 C₁₈H₃₂O₂ 
• 621-84-1 O-benzyl carbamate 
• 880872-01-5 (2R,3R,6S)-N-formyl-2-methyl-6-[10'-(2'-methyl-[1,3]-dioxolan-2-yl)-decyl]-piperidin-3-yl acetate 
• 494825-66-0 (2R,3R,6R)-2-methyl-N-tert-butoxycarbonyl-3-methoxymethoxy-6-(11'-oxo-2'-dodecyl)piperidine 

Downstream Products

• 5227-24-7 3 β epi-3 cassine 

Relevant articles and documents

A direct and general method for the reductive alkylation of tertiary lactams/amides: Application to the step economical synthesis of alkaloid (-)-morusimic acid D

Full details of the direct and general method for the reductive alkylation of tertiary lactams and amides to give tertiary sec-alkylamines are presented. This one-pot method consists of in situ activation of a lactam or an amide with Tf2O/DTBMP, addition of a Grignard reagent, and reduction of the resulting iminium intermediates. Alkyl, benzyl, and aryl Grignard reagents and several reductants or reducing conditions (LiAlH4, NaBH4, Hantzsch ester, Bu3SnH, Pd(OH)2/C, H2) could be used effectively. Reductive alkylations of substituted lactams demonstrated good to excellent 1,3-asymmetric induction to provide the corresponding di- or trisubstituted pyrrolidine/piperidine in 6:1 (LiAlH4), 11:1 (Et 3SiH), and 20:1 (catalytic hydrogenation) cis/trans diastereoselectivity, respectively. The versatility of this methodology was demonstrated by its application in the concise stereoselective synthesis of piperidine alkaloid (-)-morusimic acid.

A new synthetic route to (-)-cassine via asymmetric aminohydroxylation

(-)-Cassine has been synthesized by a new route, asymmetric aminohydroxylation followed by reductive amination.

Total synthesis of (-)-cassine.

The PdCl(2)-catalyzed cyclization of amino allylic alcohol 16 gave the cyclized product 17a with excellent diastereoselectivity. The versatility of compound 17a as the building block for synthesizing cis-2,6-disubstituted piperidine alkaloids has been dem