(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
• Mol file: 1335060-74-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tet.2011.07.090

Reference yield:

1-(2-amino-5-methoxyphenyl)-2-chloroethan-1-one (64605-34-1) → (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate (1335060-74-6)

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:

4-methoxy-aniline (104-94-9) → (Z)-allyl 3-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-4-hydroxymethyl-6-methoxyquinoline-1(2H)-carboxylate (1335060-74-6)

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

upstream raw materials:

4-[2-(2-chloroacetyl)-4-methoxyphenylamino]butan-2-one

8-methoxy-3-methyl-1,3-dihydrofuro[3,4-c]quinolin-3-ol

1-[4-(tert-butyldimethylsilyloxymethyl)-6-methoxyquinolin-3-yl]ethanone

4-tert-butyldimethylsilyloxymethyl-3-[1-(3,4-dimethoxybenzyloxy)ethyl]-6-methoxyquinoline

Downstream raw materials:

(Z)-allyl 1a-[1-(3,4-dimethoxybenzyloxy)ethyl]-2-(hex-3-ene-1,5-diynyl)-7b-(hydroxymethyl)-6-methoxy-1a,2-dihydrooxireno[2,3-c]quinoline-3(7bH)-carboxylate

(Z)-allyl 1a-[1-(3,4-dimethoxybenzyloxy)ethyl]-7b-formyl-2-(hex-3-ene-1,5-diynyl)-6-methoxy-1a,2-dihydrooxireno[2,3-c]quinoline-3(7bH)-carboxylate