CID 6540490

Base Information

• Chemical Name: CID 6540490
• CAS No.: 495-83-0
• Molecular Formula: C13H21NO2
• Molecular Weight: 223.315
• European Community (EC) Number: 207-810-5
• Wikipedia: Tigloidine
• NCI Thesaurus Code: C152623
• Mol file: 495-83-0.mol

Synonyms:Tigloidine

Chemical Property of CID 6540490

Chemical Property:

• Vapor Pressure: 0.0021mmHg at 25°C
• Boiling Point: 290.2°Cat760mmHg
• PKA: 10.03±0.40(Predicted)
• Flash Point: 99.9°C
• PSA: 29.54000
• Density: 1.06g/cm³
• LogP: 2.05890
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 223.157228913
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Tigloyltropeine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC1CC2CCC(C1)N2C
• Isomeric SMILES: C/C=C(/C)\C(=O)OC1C[C@H]2CC[C@@H](C1)N2C
• Description: A tropine alkaloid isolated from Duboisia rnyoporoides, this base is a colourless syrup which yields crystalline salts. The hydrobromide forms colourless, tabular crystals m.p. 234-5°C and is optically inactive; the aurichloride crystallizes as yellow plates, m.p. 213.5- 2140 C; the picrate as yellow rectangular plates, m.p. 239°C and the methiodide as square plates, m.p. 244-5°C. The alkaloid is unsaturated and the hydro bromide, on hydrogenation, furnishes dihydrotigloidine, giving a picrate, m.p. l34-5°C. When treated with bromine in CHC13 it forms dibromodihydrotigloidine, m.p. 187°C (dec.). The free base may be hydrolyzed by boiling with H20 when it furnishes pseudotropine and tiglic acid. The base is therefore the tiglyl ester of pseudotropine. By comparison, tiglyltropine gives a hydrobromide with m.p. 207°C and a picrate, m.p. 200°C.

Technology Process of CID 6540490

There total 3 articles about CID 6540490 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:

pseudotropine (135-97-7) → 3β-tigloyloxytropane (495-83-0)

Guidance literature:

With tigloyl-CoA; at 30 ℃; for 1h; Product distribution; Rate constant; various substrates;

DOI:10.1016/0031-9422(94)00907-B

Reference yield:

(E)-2-methylbut-2-enoyl chloride (35660-94-7) → 3β-tigloyloxytropane (495-83-0)

Guidance literature:

Reference yield:

pseudotropine (135-97-7) → 3β-tigloyloxytropane (495-83-0)

Guidance literature:

Further Variations:; Reaction partners; Product distribution;

DOI:10.1016/S0031-9422(99)00293-9

upstream raw materials:

pseudotropine

(E)-2-methylbut-2-enoyl chloride

Refernces

• 1、 Boswell, Henry D.,Draì?ger, Birgit,McLauchlan, W. Russell,Portsteffen, Andreas,Robins, David J.,Robins, Richard J.,Walton, Nicholas J.. "Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura". . p. 871 - 878. Retrieved 2007/10/03.