(R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid

Base Information

• Chemical Name: (R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid
• CAS No.: 92977-00-9
• Molecular Formula: C10H11 N O2
• Molecular Weight: 177.2
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID30446770
• Wikidata: Q72506882
• Mol file: 92977-00-9.mol

Synonyms:92977-00-9;(R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID;(R)-1,2,3,4-TETRAHYDROQUINOLINE-2-CARBOXYLIC ACID;(2R)-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid;D-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid;(R)-1,2,3,4-Tetrahydroquinoline-2-carboxylicacid;SCHEMBL1531662;DTXSID30446770;AKOS024258406;A844410

Chemical Property of (R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid

Chemical Property:

• PSA: 49.33000
• LogP: 1.63590
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

97% ^*data from raw suppliers

(R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLICACID 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=CC=C2NC1C(=O)O
• Isomeric SMILES: C1CC2=CC=CC=C2N[C@H]1C(=O)O

Technology Process of (R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid

There total 13 articles about (R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic 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: 50.0%

1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester (63430-79-5) → 1,2,3,4-tetrahydroquinolic acid (92976-98-2) + (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (92977-00-9)

Guidance literature:

With α-chymotrypsin; In aq. phosphate buffer; at 20 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1021/jm501119j

Reference yield:

quinoline-2-carboxylic acid (93-10-7,1199266-78-8) → 1,2,3,4-tetrahydroquinolic acid (92976-98-2) + (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (92977-00-9)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In toluene; at 20 ℃; for 17h; under 37503.8 Torr; Overall yield = 82 %Chromat.; Inert atmosphere; Autoclave;

DOI:10.1016/j.tet.2013.07.090

Reference yield:

quinoline (91-22-5) → (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (92977-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: (R)-[3,3'-(OCH₂P(O)(oMePh)2)2-2,2'-diyl-1,1'-biNaphth]AlCl / CH₂Cl₂; toluene / 64 h / -40 °C

2: H₂ / Rh/C / ethyl acetate / 7 h / 760.05 Torr

3: LiOH*H₂O; H₂O₂ / H₂O; methanol / 1 h / cooling

4: aq. HCl / 10 h / Heating

With hydrogenchloride; lithium hydroxide; (R)-[3,3'-(OCH₂P(O)(oMePh)2)2-2,2'-diyl-1,1'-biNaphth]AlCl; hydrogen; dihydrogen peroxide; Rh on carbon; In methanol; dichloromethane; water; ethyl acetate; toluene; 1: Reissert-type reaction;

DOI:10.1021/ja010654n

upstream raw materials:

1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester

(R)-1-Benzoyl-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid amide

quinoline

(R)-N-(2-furoyl)-2-cyano-1,2-dihydroquinoline

Downstream raw materials:

methyl (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylate

(R)-(+)-N-[4-(4-phenylpiperazin-1-yl)butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide

(R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide

(R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide