(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

Base Information

Chemical Name:(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
CAS No.:1335136-65-6
Molecular Formula:C₃₂H₃₃NO₈
Molecular Weight:559.616
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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: 62.0%

: 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

: 1335136-65-6
(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

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; In octane; dichloromethane; at -20 ℃; for 5h; regioselective reaction; Molecular sieve;
DOI:10.1016/j.tet.2011.07.090

Reference yield:

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

: 1335136-65-6
(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

Guidance literature:: Multi-step reaction with 8 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

8.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / octane; dichloromethane / 5 h / -20 °C / Molecular sieve

With 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium tetrahydroborate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; octane; 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

: 1335136-65-6
(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

Guidance literature:: Multi-step reaction with 9 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

9.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / octane; dichloromethane / 5 h / -20 °C / Molecular sieve

With 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium tetrahydroborate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; boron trichloride; titanium tetrachloride; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; octane; 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