(E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester

Base Information

• Chemical Name: (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester
• CAS No.: 189886-33-7
• Molecular Formula: C₂₄H₃₀NO₆P
• Molecular Weight: 459.479
• Mol file: 189886-33-7.mol

Synonyms:(E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester

Chemical Property of (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester

There total 9 articles about (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl 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%

(6-Methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-yl)-methanol (189886-21-3) + (E)-3-(4-Phosphono-phenyl)-acrylic acid isopropyl ester (189886-30-4) → (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester (189886-33-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 3h; Heating;

DOI:10.1039/a606968a

Reference yield:

6-methoxy quinoline (5263-87-6) → (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester (189886-33-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / acetone / Heating

2: 94 percent / K₃Fe(CN)6, aq. KOH / toluene / 0.25 h / 35 °C

3: 85 percent / H₂ / Pd/C / ethanol / 48 h / 30400 Torr / Ambient temperature

4: 70 percent / LDA / tetrahydrofuran / -78 °C

5: 75 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

6: 67 percent / DCC, DMAP / tetrahydrofuran / 3 h / Heating

With dmap; potassium hydroxide; lithium aluminium tetrahydride; hydrogen; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; acetone; toluene;

DOI:10.1039/a606968a

Reference yield:

6-Methoxy-1-methyl-2-oxo-1,2-dihydroquinoline (5392-11-0) → (E)-3-{4-[Hydroxy-(6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phosphoryl]-phenyl}-acrylic acid isopropyl ester (189886-33-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / H₂ / Pd/C / ethanol / 48 h / 30400 Torr / Ambient temperature

2: 70 percent / LDA / tetrahydrofuran / -78 °C

3: 75 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

4: 67 percent / DCC, DMAP / tetrahydrofuran / 3 h / Heating

With dmap; lithium aluminium tetrahydride; hydrogen; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1039/a606968a

upstream raw materials:

(6-Methoxy-1-methyl-1,2,3,4-tetrahydro-quinolin-3-yl)-methanol

(E)-3-(4-Phosphono-phenyl)-acrylic acid isopropyl ester

6-methoxy quinoline

6-Methoxy-1-methyl-2-oxo-1,2-dihydroquinoline