2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde

Base Information

• Chemical Name: 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde
• CAS No.: 1414367-72-8
• Molecular Formula: C₁₉H₁₉NO₃
• Molecular Weight: 309.365
• Mol file: 1414367-72-8.mol

Synonyms:2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde

Chemical Property of 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde

There total 7 articles about 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde 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: 99.0%

5-ethenyl-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (1414367-71-7) → 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde (1414367-72-8)

Guidance literature:

5-ethenyl-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one; With ozone; In dichloromethane; at -78 ℃; for 0.0833333h;

In dichloromethane; Inert atmosphere;

DOI:10.1021/ml500055h

Reference yield:

1-hydroxy-naphthalene-2-carboxylic acid methyl ester (948-03-8) → 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde (1414367-72-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 1 h / -5 °C

2.1: lithium chloride / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere

3.1: bromine; acetic acid / 20 - 90 °C / Inert atmosphere

4.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 90 °C / Inert atmosphere

5.1: tetrahydrofuran / 15 h

6.1: tricyclohexylphosphine; potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 140 °C / Inert atmosphere; Microwave irradiation

7.1: ozone / 0.08 h / -78 °C

7.2: resin-bound triphenylphosphine / Inert atmosphere

With potassium phosphate; N-Bromosuccinimide; bromine; ozone; acetic acid; lithium chloride; tricyclohexylphosphine; dibenzoyl peroxide; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; pyridine; tetrachloromethane; water; N,N-dimethyl-formamide;

Reference yield:

methyl 1-methyl-2-naphthoate (73721-17-2) → 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde (1414367-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bromine; acetic acid / 20 - 90 °C / Inert atmosphere

2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 90 °C / Inert atmosphere

3.1: tetrahydrofuran / 15 h

4.1: tricyclohexylphosphine; potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 140 °C / Inert atmosphere; Microwave irradiation

5.1: ozone / 0.08 h / -78 °C

5.2: resin-bound triphenylphosphine / Inert atmosphere

With potassium phosphate; N-Bromosuccinimide; bromine; ozone; acetic acid; tricyclohexylphosphine; dibenzoyl peroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; water;

upstream raw materials:

1-hydroxy-naphthalene-2-carboxylic acid methyl ester

methyl 1-methyl-2-naphthoate

methyl 4-bromo-1-methyl-2-naphthoate

methyl 4-bromo-1-(bromomethyl)-2-naphthoate

Downstream raw materials:

1-({2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl}methyl)-4-(pyridine-2-yl)piperidine-4-carbonitrile

5-{[4-fluoro-4-(pyridine-2-yl)piperidine-1-yl]methyl}-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one

1-({2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl}methyl)-4-phenylpiperidine-4-carbonitrile

1-({2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl}methyl)-4-(4-methylpyridin-2-yl)piperidine-4-carbonitrile