Trachelanthamidine

Base Information

• Chemical Name: Trachelanthamidine
• CAS No.: 526-64-7
• Molecular Formula: C8H15 N O
• Molecular Weight: 141.21
• Hs Code.: 2933990090
• UNII: G32020EJYI
• DSSTox Substance ID: DTXSID201318955
• Nikkaji Number: J8.644D
• Wikidata: Q27114838
• Metabolomics Workbench ID: 68368
• Mol file: 526-64-7.mol

Synonyms:trachelanthamidine

Chemical Property of Trachelanthamidine

Chemical Property:

• Vapor Pressure: 0.0753mmHg at 25°C
• Boiling Point: 201.6°Cat760mmHg
• Flash Point: 81.1°C
• PSA: 23.47000
• Density: 1.09g/cm³
• LogP: 0.40090
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 141.115364102
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

98%min ^*data from raw suppliers

Trachelanthamidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(CCN2C1)CO
• Isomeric SMILES: C1C[C@H]2[C@@H](CCN2C1)CO
• Uses: Trachelanthamidine is a pyrrolizidine alkaloid as serotonin 5-HT4 receptor.

Technology Process of Trachelanthamidine

There total 88 articles about Trachelanthamidine 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: 99.0%

(1R,7aS)-1-(hydroxymethyl)-tetrahydro-1H-pyrrolizin-3(2H)-one (916312-92-0) → laburnine (526-64-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 12h; Heating;

DOI:10.1055/s-2006-949605

Reference yield: 88.0%

(1R,7aS)-Hexahydro-1-<(propanoyloxy)methyl>-3H-pyrrolizin-3-one (147949-53-9) → laburnine (526-64-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1021/jo00061a005

Reference yield: 86.0%

(1R,8S)-1-(acetoxymethyl)pyrrolizidin-3-one (105706-73-8) → laburnine (526-64-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1016/j.tet.2008.06.005

upstream raw materials:

3-(2(R)-(5-oxo-2(S)-pyrrolidinyl)-4-chlorobutyryl)-4(S)-isopropyl-1,3-thiazolidine-2-thione

(S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methanesulfonyloxy-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

curassavine

ethyl (-)-6β-hydroxy-8α-pyrrolizidine-1β-carboxylate

Downstream raw materials:

SC 53606

4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide

4-(acetylamino)-N-[(7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-5-chloro-2-methoxybenzamide

Refernces

• 1、 Al-Jaber, Hala I.,Mosleh, Ibrahim M.,Mallouh, Abdallah,Abu Salim, Omar M.,Abu Zarga, Musa H.. "Chemical constituents of Osyris alba and their antiparasitic activities". . p. 814 - 820. Retrieved 2010.
• 2、 Appayee, Chandrakumar,Sarkale, Abhijeet M.. "Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids". . . Retrieved 2020/06/05.
• 3、 Koley, Dipankar,Krishna, Yarkali,Srinivas, Kyatham,Khan, Afsar Ali,Kant, Ruchir. "Organocatalytic asymmetric mannich cyclization of hydroxylactams with acetals: Total syntheses of ( )-epilupinine, ( )-tashiromine, and ( )-trachelanthamidine". supporting information. p. 13196 - 13200. Retrieved 2015/02/19.