(2S)-2-methyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: (2S)-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 200125-70-8
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• DSSTox Substance ID: DTXSID901337229
• Nikkaji Number: J343.046D
• Mol file: 200125-70-8.mol

Synonyms:200125-70-8;(s)-2-methyl-1,2,3,4-tetrahydroquinoline;(2S)-2-methyl-1,2,3,4-tetrahydroquinoline;Quinoline, 1,2,3,4-tetrahydro-2-methyl-, (2S)-;SCHEMBL1734662;DTXSID901337229;AKOS006352882;2beta-Methyl-1,2,3,4-tetrahydroquinoline;(2S)-1,2,3,4-Tetrahydro-2-methylquinoline

Chemical Property of (2S)-2-methyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Boiling Point: 89 °C (5 mmHg)
• PKA: 5.15±0.40(Predicted)
• PSA: 12.03000
• Density: 0.966±0.06 g/cm3(Predicted)
• LogP: 2.57120
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.104799419
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

NLT 98% ^*data from raw suppliers

(2S)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=CC=CC=C2N1
• Isomeric SMILES: C[C@H]1CCC2=CC=CC=C2N1

Technology Process of (2S)-2-methyl-1,2,3,4-tetrahydroquinoline

There total 81 articles about (2S)-2-methyl-1,2,3,4-tetrahydroquinoline 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: 40.0%

(S)-1-(2-naphthyl-sulfonyl)pyrrolidine-2-carbonyl chloride (91872-31-0) + 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4) → (2R,2'S)-2-methyl-N-[N'-(2-naphthylsulfonyl)prolyl]-1,2,3,4-tetrahydroquinoline + (2S,2'S)-2-methyl-N-[N'-(2-naphthylsulfonyl)prolyl]-1,2,3,4-tetrahydroquinoline + (S)-2-methyl-1,2,3,4-tetrahydroquinoline (200125-70-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8)

Guidance literature:

In toluene; at 20 ℃; for 6h; diastereoselective reaction; Resolution of racemate;

DOI:10.1007/s10593-014-1538-8

Reference yield: 40.0%

tert-butyl 4-chlorobenzoate (712-95-8) + 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4) → tert-butyl (S)-4-(2-methyl-3,4-dihydroquinolin-1(2H)-yl)benzoate + (S)-2-methyl-1,2,3,4-tetrahydroquinoline (200125-70-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 7,9-bis(4-methyl-2,6-bis((R)-1-phenylethyl)phenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate; lithium tert-butoxide; In Cyclopentane; at 0 ℃; for 24h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.202103803

Reference yield: 38.0%

N-phthaloyl-3-cyclohexyl-(S)-alanyl chloride (1416453-17-2) + 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4) → (2S)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline (1416453-25-2) + (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline (1416453-26-3) + (S)-2-methyl-1,2,3,4-tetrahydroquinoline (200125-70-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 6h; stereoselective reaction;

DOI:10.1016/j.tetasy.2012.11.001

upstream raw materials:

2-methylquinoline

N-tosyl-L-prolyl chloride

1,2,3,4-tetrahydro-2-methylquinoline

N-[N'-phthaloyl-(2S)-alanyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline

Downstream raw materials:

1-(4-methylbenzenesulfonyl)-2-methyl-1,2,3,4-tetrahydroquinoline

(2S)-2-methyl-1-[o-methyl-N-phthaloyl-(S)-tyrosyl]-1,2,3,4-tetrahydroquinoline

(2S)-2-methyl-1-[3-(4-nitrophenyl)-N-phthaloyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline

Refernces

• 1、 Krasnov, Victor P.,Levit, Galina L.,Kodess, Mikhail I.,Charushin, Valery N.,Chupakhin, Oleg N.. "N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines". . p. 859 - 862. Retrieved 2004.
• 2、 Liu, Chenguang,Wang, Mingyang,Liu, Shihan,Wang, Yujie,Peng, Yong,Lan, Yu,Liu, Qiang. "Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**". supporting information. p. 5108 - 5113. Retrieved 2021/01/21.
• 3、 Hong, Xin,Shi, Shi-Liang,Wang, Zi-Chao,Xie, Pei-Pei,Xu, Youjun. "Low-Temperature Nickel-Catalyzed C?N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand". supporting information. p. 16077 - 16084. Retrieved 2021/06/17.