(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one

Base Information

• Chemical Name: (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one
• CAS No.: 1240264-80-5
• Molecular Formula: C₂₄H₂₂O₆
• Molecular Weight: 406.435

Synonyms:(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one

Chemical Property of (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one

Chemical Property:

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Technology Process of (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one

There total 1 articles about (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one 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:

vanillin (121-33-5,8014-42-4) + propargyl bromide (106-96-7) + acetylacetone (123-54-6,81235-32-7) → (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,6-diene-3,5-dione (1356917-45-7) + (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one (1240264-80-5)

Guidance literature:

propargyl bromide; acetylacetone; With potassium carbonate; In acetone; toluene; at 80 ℃; for 6h;

With boron trioxide; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

vanillin; Further stages;

DOI:10.3390/molecules25133066

Reference yield: 96.0%

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one (1240264-80-5) + (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-yl 2-(2-(2-(2-(5-azidopentanamido)ethoxy)ethoxy)ethoxy)acetate → (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-yl 2-(2-(2-[2-(5-(4-[(2Z,4E)-2-[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]-5-(4-hydroxy-3-methoxyphenyl)-3-oxopent-4-en-1-yl]-1H-1,2,3-triazol-1-yl)pentanamido)ethoxy]ethoxy)ethoxy)acetate

Guidance literature:

With copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; at 35 ℃; for 24h;

DOI:10.1016/j.bmc.2015.10.032

Reference yield: 95.0%

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(prop-2-yn-1-yl)hepta-1,4,6-trien-3-one (1240264-80-5) + (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-yl 2-(2-(2-(2-(10-azidodecanamido)ethoxy)ethoxy)ethoxy)acetate → (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-yl 2-(2-(2-[2-(10-(4-[(2Z,4E)-2-[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]-5-(4-hydroxy-3-methoxyphenyl)-3-oxopent-4-en-1-yl]-1H-1,2,3-triazol-1-yl)decanamido)ethoxy]ethoxy)ethoxy)acetate

Guidance literature:

With copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; at 35 ℃; for 24h;

DOI:10.1016/j.bmc.2015.10.032

upstream raw materials:

vanillin

propargyl bromide

acetylacetone

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