N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

Base Information

Chemical Name:N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide
CAS No.:1436715-35-3
Molecular Formula:C₂₉H₃₉NO₃SSi
Molecular Weight:509.785
Hs Code.:

Synonyms:N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

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Chemical Property of N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

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Technology Process of N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

There total 7 articles about N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide 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: 48.0%

: 591-50-4
iodobenzene

: 1436715-30-8
N-((6-((tert-butyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(prop-2-yn-1-yl)-p-toluenesulfonamide

: 1436715-35-3
N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; at 40 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo400634c

Reference yield:

: 930-68-7
cyclohexenone

: 1436715-35-3
N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

Guidance literature:: Multi-step reaction with 7 steps

1: barium(II) hydroxide / methanol; water; 1-methyl-pyrrolidin-2-one / 4 h / 29 °C / Inert atmosphere

2: triethylamine / dichloromethane / 6 h / 30 °C / Inert atmosphere

3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4: triethylamine; dmap / dichloromethane / 12 h / Inert atmosphere; Reflux

5: potassium carbonate / methanol / 1 h / 30 °C / Inert atmosphere

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 °C / Inert atmosphere

7: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 12 h / 40 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; potassium carbonate; triethylamine; triphenylphosphine; barium(II) hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; 1: |Baylis-Hillman Reaction;
DOI:10.1021/jo400634c

Reference yield:

: 105956-40-9
2-(hydroxymethyl)cyclohex-2-en-1-one

: 1436715-35-3
N-((6-((tertbutyldimethylsilyl)oxy)cyclohex-1-en-1-yl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)-p-toluenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 6 h / 30 °C / Inert atmosphere

2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3: triethylamine; dmap / dichloromethane / 12 h / Inert atmosphere; Reflux

4: potassium carbonate / methanol / 1 h / 30 °C / Inert atmosphere

5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 °C / Inert atmosphere

6: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 12 h / 40 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo400634c