(+)-Calycanthine

Base Information

• Chemical Name: (+)-Calycanthine
• CAS No.: 595-05-1
• Molecular Formula: C₂₂H₂₆N₄
• Molecular Weight: 346.475
• NSC Number: 99016
• Wikidata: Q27166918
• ChEMBL ID: CHEMBL1981354
• Mol file: 595-05-1.mol

Synonyms:(+)-Calycanthine;21,24-dimethyl-3,12,21,24-tetrazahexacyclo[9.7.3.32,10.01,10.04,9.013,18]tetracosa-4,6,8,13,15,17-hexaene;NSC99016;NSC-99016;Prestwick_723;Prestwick0_000595;Prestwick1_000595;Prestwick2_000595;Oprea1_287195;5,10b:11,4b-Bis(iminoethano)dibenzo[c,h][2,6]naphthyridine, 5,6,11,12-tetrahydro-13,18-dimethyl-;MLS000728639;SPBio_002689;CHEMBL1981354;CHEBI:95133;XSYCDVWYEVUDKQ-UHFFFAOYSA-N;HMS1569H12;HMS2270J12;LSM-6401;NCI60_042216;SMR000470815;Q27166918;(1S,2S,10S,11S)-21,24-Dimethyl-3,12,21,24-tetrazahexacyclo[9.7.3.32,10.01,10.04,9.013,18]tetracosa-4,6,8,13,15,17-hexaene;5,10b:11,4b-Bis(iminoethano)dibenzo[c,h][2,6]naphthyridine, 5,6,11,12-tetrahydro-13,18-dimethyl-, [4bS-(4b.alpha.,5.alpha.,10b.alpha.,11.alpha.)]-;5,4b-Bis(iminoethano)dibenzo[c,h][2,6]naphthyridine, 5,6,11,12-tetrahydro-13,18-dimethyl-;5,4b-Bis(iminoethano)dibenzo[c,h][2,6]naphthyridine, 5,6,11,12-tetrahydro-13,18-dimethyl-, [4bS-(4b.alpha.,5.alpha.,10b.alpha.,11.alpha.)]-

Chemical Property of (+)-Calycanthine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 245° (evac tube)
• Boiling Point: 531.8°Cat760mmHg
• Flash Point: 310.3°C
• PSA: 30.54000
• Density: 1.29g/cm³
• LogP: 3.18840
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 346.21574685
• Heavy Atom Count: 26
• Complexity: 531

Purity/Quality:

≥98% ^*data from raw suppliers

Calycanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4NC5=CC=CC=C5C2(C1NC6=CC=CC=C36)CCN4C
• Description: This dimeric alkaloid has recently been isolated from the stems and leaves of dried Palicourea alpina

Technology Process of (+)-Calycanthine

There total 41 articles about (+)-Calycanthine 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: 60.0%

(-)-Chimonanthine (4147-36-8,4147-37-9,5545-89-1,23102-84-3,85610-66-8) → Calycanthin (595-05-1,16739-56-3,85548-42-1)

Guidance literature:

With acetic acid; Heating;

DOI:10.1021/ja991714g

Reference yield: 57.0%

(+)-Chimonanthine (4147-36-8,4147-37-9,5545-89-1,23102-84-3,85610-66-8) → (4bR,5S,10bR,11S)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine (595-05-1,16739-56-3,85548-42-1)

Guidance literature:

With acetic acid; In water; at 95 ℃; for 48h; Inert atmosphere;

DOI:10.1002/anie.201201132

Reference yield: 48.0%

C24H26N4O4 → (4bR,5S,10bR,11S)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine (595-05-1,16739-56-3,85548-42-1)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.1c10498

upstream raw materials:

(-)-Chimonanthine

2-iodophenylamine

2,2'-((3S,3'S)-1,1'-dibenzyl-2,2'-dioxo-[3,3'-biindoline]-3,3'-diyl)diacetaldehyde

8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

Downstream raw materials:

dibenzo[c,h][2,6]naphthyridine

Refernces

• 1、 Shen, Xianfu,Zhou, Yongyun,Xi, Yongkai,Zhao, Jingfeng,Zhang, Hongbin. "Copper catalyzed sequential arylation-oxidative dimerization of o-haloanilides: synthesis of dimeric HPI alkaloids". supporting information. p. 14873 - 14876. Retrieved 2015/10/06.
• 2、 Movassaghi, Mohammad,Schmidt, Michael A.. "Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine". . p. 3725 - 3728. Retrieved 2008/03/11.