(+)-(R)-2-(1-Benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione

Base Information

• Chemical Name: (+)-(R)-2-(1-Benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
• CAS No.: 152903-44-1
• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.311
• DSSTox Substance ID: DTXSID80453994
• Nikkaji Number: J1.493.270D
• Wikidata: Q82275305
• Mol file: 152903-44-1.mol

Synonyms:152903-44-1;(+)-(R)-2-(1-BENZYL-2-HYDROXYETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE;(R)-2-(1-hydroxymethyl-2-phenylethyl)isoindole-1,3-dione;SCHEMBL1237351;DTXSID80453994;WUQQWFQBZMAJLS-CYBMUJFWSA-N;(R)-2-Phthalimidyl-3-phenyl-1-propanol

Chemical Property of (+)-(R)-2-(1-Benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 281.10519334
• Heavy Atom Count: 21
• Complexity: 379

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CO)N2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H](CO)N2C(=O)C3=CC=CC=C3C2=O

Technology Process of (+)-(R)-2-(1-Benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione

There total 6 articles about (+)-(R)-2-(1-Benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione 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: 96.0%

phthalic anhydride (85-44-9) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1)

Guidance literature:

at 140 ℃;

DOI:10.1016/j.tetlet.2005.04.011

Reference yield: 80.0%

2-((S)-2-Bromo-1-hydroxymethyl-2-phenyl-ethyl)-isoindole-1,3-dione → (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

Reference yield:

phthalic anhydride (85-44-9) → (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / xylene / 2 h / Heating

2: 1.) SOCl₂, 2.) LiBr / 1.) CHCl₃, 8 h, 2.) Me₂CO, 6 h

3: 80 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With lithium aluminium tetrahydride; thionyl chloride; lithium bromide; In tetrahydrofuran; xylene;

upstream raw materials:

phthalic anhydride

(R)-2-amino-3-phenylpropanol

(1S,2S)-2-amino-1-phenyl-1,3-diol

(1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol

Downstream raw materials:

(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

(+)-N,N-Phthaloyl-O¹-tosyl-D-phenylalaninol

(R)-2-amino-3-phenylpropanol

(+)-(R)-2-[1-benzyl-2-(2,6-dimethylphenoxy)ethyl]-1H-isoindole-1,3(2H)-dione