(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

Base Information

Chemical Name:(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate
CAS No.:1335060-74-6
Molecular Formula:C₃₂H₃₃NO₇
Molecular Weight:543.617
Hs Code.:

Synonyms:(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

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Chemical Property of (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

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Technology Process of (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

There total 11 articles about (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate 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: 88.0%

: (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-4-tert-butyldimethylsilyloxymethyl-6-methoxy-2-(6-triisopropylsilylhex-3-ene-1,5-diynyl)quinoline-1(2H)-carboxylate

: 1335060-74-6
(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/j.tet.2011.07.090

Reference yield:

: 64605-34-1
1-(2-amino-5-methoxyphenyl)-2-chloroethan-1-one

: 1335060-74-6
(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 24 h / 65 °C / Sealed tube

2.1: methanol; potassium carbonate / 3 h / Inert atmosphere; Reflux

3.1: 1-methyl-1H-imidazole; iodine / dichloromethane / 5 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 0 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

5.2: 0 - 20 °C

6.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 20 °C

6.2: 1 h / -18 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

With 1-methyl-1H-imidazole; methanol; sodium tetrahydroborate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; mineral oil; 6.1: Reissert type reaction / 6.2: Reissert type reaction;
DOI:10.1016/j.tet.2011.07.090

Reference yield:

: 104-94-9
4-methoxy-aniline

: 1335060-74-6
(Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: boron trichloride; titanium tetrachloride / dichloromethane; toluene / 0 - 120 °C

1.2: 1 h / Reflux

1.3: 0 °C / pH 4

2.1: tetrahydrofuran / 24 h / 65 °C / Sealed tube

3.1: methanol; potassium carbonate / 3 h / Inert atmosphere; Reflux

4.1: 1-methyl-1H-imidazole; iodine / dichloromethane / 5 h / 20 °C

5.1: sodium tetrahydroborate / methanol / 0 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

6.2: 0 - 20 °C

7.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 20 °C

7.2: 1 h / -18 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

With 1-methyl-1H-imidazole; methanol; sodium tetrahydroborate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; boron trichloride; titanium tetrachloride; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; 1.1: Sugasawa reaction / 1.2: Sugasawa reaction / 7.1: Reissert type reaction / 7.2: Reissert type reaction;
DOI:10.1016/j.tet.2011.07.090