(S)-4,5-Didehydropipecolic acid

Base Information

• Chemical Name: (S)-4,5-Didehydropipecolic acid
• CAS No.: 31456-71-0
• Molecular Formula: C6H9 N O2
• Molecular Weight: 127.143
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID20331580
• Nikkaji Number: J544.804B
• Wikidata: Q27107119
• Metabolomics Workbench ID: 68836
• Mol file: 31456-71-0.mol

Synonyms:4,5-dehydropipecolic acid;4,5-dehydropipecolic acid, (+-)-isomer;4,5-dehydropipecolic acid, (S)-isomer

Chemical Property of (S)-4,5-Didehydropipecolic acid

Chemical Property:

• Boiling Point: 277.9±40.0 °C(Predicted)
• PKA: 2.23±0.20(Predicted)
• PSA: 49.33000
• Density: 1.176±0.06 g/cm3(Predicted)
• LogP: 0.31790
• Storage Temp.: 2-8°C
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 142

Purity/Quality:

98% ^*data from raw suppliers

(S)-1,2,3,6-Tetrahydropyridine-2-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCNC1C(=O)O
• Isomeric SMILES: C1C=CCN[C@@H]1C(=O)O

Technology Process of (S)-4,5-Didehydropipecolic acid

There total 15 articles about (S)-4,5-Didehydropipecolic acid 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: 72.0%

(2S)-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid (305836-78-6) → (2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid (31456-71-0)

Guidance literature:

With sodium amalgam; sodium phosphate; In methanol; at 20 ℃; for 5h;

DOI:10.3987/COM-06-10874

Reference yield: 61.0%

methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate (282527-09-7) → (2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid (31456-71-0)

Guidance literature:

methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate; With potassium carbonate; thiophenol; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

With lithium hydroxide; In methanol; water; at 20 ℃; for 24h; Further stages.;

DOI:10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO;2-8

Reference yield:

methyl 2-[(1-benzyloxyallyl)-(4-nitrobenzenesulfonyl)amino]-(S)-pent-4-enoate (282527-06-4) → (2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid (31456-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / RuCl₂[PCy₃]2[=CHPh] / CH₂Cl₂ / 16 h / 20 °C

2.1: 88 percent / triethylsilane; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

3.1: K₂CO₃; thiophenol / dimethylformamide / 24 h / 20 °C

3.2: 61 percent / LiOH / methanol; H₂O / 24 h / 20 °C

With triethylsilane; boron trifluoride diethyl etherate; potassium carbonate; thiophenol; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO;2-8

upstream raw materials:

(S)-methyl 1,2,3,6-tetrahydropyridine-2-carboxylate

(2S,4'S,5'R)-[(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)(1,3,4,6-tetrahydro-2-pyridinyl)]methanone

methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

(2S)-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid

Downstream raw materials:

(S)-1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid

(2S)-N-benzoyl-2-piperidinecarboxylic acid

pipecolinic acid

(S)-1-benzoyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid

Refernces

• 1、 Kinderman, Sape S.,Doodeman, Robin,Van Beijma, Jetze W.,Russcher, Jaap C.,Tjen, Kim C. M. F.,Kooistra, T. Martijn,Mohaselzadeh, Homayun,Van Maarseveen, Jan H.,Hiemstra, Henk,Schoemaker, Hans E.,Rutjes, Floris P. J. T.. "Ring-closing metathesis of allylic O,O- and N,O-acetals". . p. 736 - 748. Retrieved 2007/10/03.
• 2、 Guillena,Najera. "1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids". . p. 7310 - 7322. Retrieved 2007/10/03.