((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone

Base Information

• Chemical Name: ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone
• CAS No.: 1196666-10-0
• Molecular Formula: C₁₇H₁₄ClNO₄
• Molecular Weight: 331.755

Synonyms:((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone

Chemical Property of ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone

Chemical Property:

Purity/Quality:

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Technology Process of ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone

There total 4 articles about ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone 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: 68.0%

α-nitro-α-diazo-p-methoxyacetophenone (1196665-69-6) + 2-chlorostyrene (2039-87-4,107830-52-4,26125-41-7) → ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone (1196666-10-0)

Guidance literature:

2-chlorostyrene; With tetrakis[(S)-(N-tetrachlorophthalimido)-tert-lucinato]dirhodium(II); In diethyl ether; at -40 ℃; for 0.25h; Inert atmosphere;

α-nitro-α-diazo-p-methoxyacetophenone; In diethyl ether; at -40 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja9044955

Reference yield:

1-(4-methoxybenzoyl)-imidazole (10364-93-9) → ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone (1196666-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

1.2: 16 h / Inert atmosphere; Reflux

2.1: pyridine; triflic azide / hexane; acetonitrile / 16 h / 0 - 20 °C / Inert atmosphere

3.1: dmap; tetrakis[(S)-(N-tetrachlorophthalimido)-tert-lucinato]dirhodium(II) / diethyl ether / 16 h / -45 °C / Inert atmosphere

With pyridine; dmap; tetrakis[(S)-(N-tetrachlorophthalimido)-tert-lucinato]dirhodium(II); triflic azide; sodium hydride; In tetrahydrofuran; diethyl ether; hexane; acetonitrile; mineral oil;

DOI:10.1021/ja201237j

Reference yield:

4-methoxybenzoylnitromethane (46318-58-5) → ((1S,2S)-(Z)-2-(2-chlorophenyl)-1-nitrocyclopropyl)(4-methoxyphenyl)methanone (1196666-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; triflic azide / hexane; acetonitrile / 16 h / 0 - 20 °C / Inert atmosphere

2: dmap; tetrakis[(S)-(N-tetrachlorophthalimido)-tert-lucinato]dirhodium(II) / diethyl ether / 16 h / -45 °C / Inert atmosphere

With pyridine; dmap; tetrakis[(S)-(N-tetrachlorophthalimido)-tert-lucinato]dirhodium(II); triflic azide; In diethyl ether; hexane; acetonitrile;

DOI:10.1021/ja201237j

upstream raw materials:

α-nitro-α-diazo-p-methoxyacetophenone

2-chlorostyrene

1-(4-methoxybenzoyl)-imidazole

4-methoxybenzoylnitromethane

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