3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

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Chemical Name:3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
CAS No.:1420376-95-9
Molecular Formula:C₁₉H₂₃N₂O₉P
Molecular Weight:454.373
Hs Code.:

Synonyms:3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

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Chemical Property of 3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

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Technology Process of 3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

There total 6 articles about 3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 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: 67.0%

: 1420376-77-7
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

: 99-33-2
3,5-dinitrobenoyl chloride

: 1420376-95-9
3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Guidance literature:: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate; With diisobutylaluminium hydride; In toluene; at -78 - 20 ℃; Inert atmosphere;

3,5-dinitrobenoyl chloride; With pyridine; dmap; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.021

Reference yield: 52.0%

: 1420376-74-4
(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

: 99-33-2
3,5-dinitrobenoyl chloride

: 1420376-95-9
3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Guidance literature:: (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate; With diisobutylaluminium hydride; In toluene; at -78 - 20 ℃; Inert atmosphere;

3,5-dinitrobenoyl chloride; With pyridine; dmap; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.021

Reference yield:

: 155795-48-5
(diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: 1420376-95-9
3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere

1.2: 4 h / 60 °C / Inert atmosphere

2.1: dihydrogen peroxide / water; dichloromethane / 1.08 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: tin(IV) chloride / dichloromethane / 12 h / -65 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

4.2: 12 h / 20 °C / Inert atmosphere

With potassium tert-butylate; dihydrogen peroxide; tin(IV) chloride; diisobutylaluminium hydride; In dichloromethane; water; dimethyl sulfoxide; toluene; 3.1: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2012.11.021