(1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate

Base Information

• Chemical Name: (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate
• CAS No.: 222972-45-4
• Molecular Formula: C₁₈H₂₆O₂Si
• Molecular Weight: 302.489
• Mol file: 222972-45-4.mol

Synonyms:(1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate

Chemical Property of (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate

There total 5 articles about (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate 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: 83.0%

(E)-3-(1-cyclohexen-1-yl)-2-propenoic acid (56453-88-4) + (Z)-(S)-6-Trimethylsilanyl-hex-3-en-5-yn-2-ol → (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate (222972-45-4)

Guidance literature:

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 18h;

Reference yield:

(E)-3-(cyclohex-1-ene)-prop-2-enoic acid methyl ester (54526-84-0) → (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate (222972-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 g / aq. NaOH / ethanol / 2.5 h / Heating

2: 2.601 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; dichloromethane;

DOI:10.1021/jo981983+

Reference yield:

methyl 3-(1'-hydroxycyclohex-1'-yl)prop-2E-enoate (85728-60-5) → (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate (222972-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Ac₂O, AcCl / acetic acid / 1.5 h / Heating

2: 84 g / aq. NaOH / ethanol / 2.5 h / Heating

3: 2.601 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; acetic anhydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; acetyl chloride; In ethanol; dichloromethane; acetic acid;

DOI:10.1021/jo981983+

upstream raw materials:

(E)-3-(1-cyclohexen-1-yl)-2-propenoic acid

(E)-3-(cyclohex-1-ene)-prop-2-enoic acid methyl ester

methyl 3-(1'-hydroxycyclohex-1'-yl)prop-2E-enoate

(1,1-dimethylethyl)dimethyl<(1S,2Z)-<(1-methyl-5-trimethylsilyl)-2-penten-4-ynyl>oxy>silane