53938-05-9

Basic information

• Product Name: Celacinnine
• Synonyms: Celacinnine
• CAS NO: 53938-05-9
• Molecular Formula: C₂₅H₃₁N₃O₂
• Molecular Weight: 405.53254
• Mol File: 53938-05-9.mol

Chemical Properties

• Boiling Point: 675.8°C at 760 mmHg
• Flash Point: 362.5°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 4.01E-18mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: Celacinnine(CAS DataBase Reference)
• NIST Chemistry Reference: Celacinnine(53938-05-9)
• EPA Substance Registry System: Celacinnine(53938-05-9)

Safety Data

• Hazardous Substances Data: 53938-05-9(Hazardous Substances Data)

Usage

Uses

There is no information provided in the materials about the specific uses of celacinnine. However, based on the general properties of macrocyclic alkaloids, they are often studied for their potential biological activities and applications in various fields such as pharmaceuticals, agrochemicals, and natural products. Further research would be needed to determine the specific applications and industries where celacinnine could be utilized.

InChI:InChI=1/C25H31N3O2/c29-24-20-23(22-12-5-2-6-13-22)26-16-7-8-18-28(19-9-17-27-24)25(30)15-14-21-10-3-1-4-11-21/h1-6,10-15,23,26H,7-9,16-20H2,(H,27,29)/b15-14+/t23-/m0/s1

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 166373-40-6 (-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one 
• 140-10-3 (E)-3-phenylacrylic acid 
• 100-52-7 benzaldehyde 
• 180324-14-5 (S)-4-phenyl-1-(2'-cyanoethyl)-1,5-diazacyclononan-2-one 
• 76598-25-9 (R)-(+)-1,5-Diaza-4-phenylbicyclo<4.3.0>nonan-2-one 
• 400782-35-6 (S)-(-)-4-phenyl-1-(3'-phthalimidopropyl)-1,5-diazacyclononan-2-one 
• 180324-13-4 (S)-(-)-4-phenyl-1-(3'-aminoethyl)-1,5-diazacyclononan-2-one 
• 163460-81-9 tert-butyl (E)-[(S)-p-tolylsulfinyl]cinnamate 
• 163460-82-0 tert-butyl (E)-[(R)-p-tolylsulfinyl]cinnamate 

Relevant articles and documents

122. Syntheses and Chiroptical Properties of the 13-Membered Spermidine Alkaloids (-)-(S)-Celacinnine, (0)-(S)-Celabenzine, (-)-(S)-Celafurine, and (+)-(S)-Viburnine

The title alkaloids were prepared from the common chiral precursor (-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one (4) which we had synthesized earlier. The spectral data for the spermidine macrocycles are in good agreement with the data reported for the isolated samples. Our experimental results indicate that the originally reported [α]D value of -2.6 (c=0.10, MeOH) for natural (S)-viburnine is erroneous and should be +17.0 (c=0.92, MeOH). As a result of the chiroptical study conducted, it can be shown empirically that all alkaloids of the 'celacinnine' type have the (S)-configuration.

Conjugate addition of 6-membered hydrazine to chiral tert-butyl (E)-2-(p-tolylsulfinyl)cinnamates. Synthesis of (S)-celacinnine

Two enantiomers of the bicyclic lactam, (S)- and (R)-9-phenyl-1,6-diazabicyclo[4.3.0]nonan-7-one (6), were synthesized stereoselectively with high optical purity (95% ee) by the asymmetric conjugate addition-cyclization of piperidazine to chiral vinyl sulfoxides, tert-butyl (E)-2-[(R)- and (S)-p-tolylsulfinyl]cinnamate (4), followed by removal of the p-tolylsulfinyl group with SmI2. The subsequent reductive cleavage of the N-N bond of the bicyclic lactam 6 with sodium in liquid ammonia produced the corresponding 9-membered azalactam, (S)- and (R)-4-phenyl-1,5-diazacyclononan-2-one (7) with 99% and 97% ee, respectively. X-ray crystallography showed that (S)-7 exists exclusively as a trans conformer in the crystal state. Starting from (S)-7, naturally occurring (S)-celacinnine 1 was synthesized with 99% ee employing the ring-expansion reaction via intramolecular transamidation.

Chiral vinyl sulfoxides as useful reagents for the synthesis of β-amino acid derivatives

(S)- and (R)-β-amino acid derivatives were synthesized by the asymmetric conjugate addition of ammonia and piperidazine to t-butyl (E)-2-[(R)-and (S)-p-tolylsulfinyl]cinnamates, respectively.

ASYMMETRIC SYNTHESIS OF CELACINNINE UTILIZING OPTICALLY ACTIVE VINYL SULFOXIDES

First asymmetric synthesis of celacinnine (10) was achieved from the nine-membered azalactam, 3-phenyl-4-azaoctanelactam (6), which was synthesized by the addition of piperidazine (4) to optically active vinyl sulfoxides (3).