(1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid

Base Information

• Chemical Name: (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid
• CAS No.: 1432500-66-7
• Molecular Formula: C₂₆H₂₆N₂O₅
• Molecular Weight: 446.503
• Mol file: 1432500-66-7.mol

Synonyms:(1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid

Chemical Property of (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid

Chemical Property:

• Boiling Point: 693.1±55.0 °C(Predicted)
• Density: 1.354±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

ML334 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: ML 334 is an inhibitor of Keap1-Nrf2 interaction and affects the cytoprotective responses to oxidative and electrophilic stress. May be used in cancer treatment and attenuation.

Technology Process of (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid

There total 32 articles about (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-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: 49.0%

benzyl-(1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylate (1432065-37-6) → (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid (1432500-66-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; ethanol; ethyl acetate; for 48h; stereoselective reaction;

DOI:10.1002/cmdc.201300525

Reference yield:

(1S,2R)-benzyl 2-(1-((1,3-dioxoisoindolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclohexane carboxylate → (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid (1432500-66-7) + C26H26N2O5 (1432065-35-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 48h; Overall yield = 77 %;

Reference yield:

2-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)-1H-isoindole-1,3(2H)-dione (310451-86-6) + 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid (1432500-66-7) + C26H26N2O5 (1432065-33-2) + C26H26N2O5 (1432065-34-3) + C26H26N2O5 (1432065-35-4)

Guidance literature:

In para-xylene;

DOI:10.1016/j.bmcl.2013.03.013

upstream raw materials:

2-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)-1H-isoindole-1,3(2H)-dione

1,2-cis-cyclohexanedicarboxylic anhydride

phenethylamine

N-phthaloylglycine

Downstream raw materials:

benzyl-(1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylate