ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate

Base Information

• Chemical Name: ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate
• CAS No.: 1026853-05-3
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 1026853-05-3.mol

Synonyms:ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate

Chemical Property of ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate

There total 2 articles about ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate 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:

3-(cyclohex-1-en-1-yl)propiolaldehyde (15341-64-7) + 2-(tert-Butyloxycarbonylamino)-2-(diethoxyphosphoryl)essigsaeure-ethylester (83027-00-3) → ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate (1026853-05-3)

Guidance literature:

2-(tert-Butyloxycarbonylamino)-2-(diethoxyphosphoryl)essigsaeure-ethylester; With potassium tert-butylate; In dichloromethane; at -78 ℃; for 0.5h;

3-(cyclohex-1-en-1-yl)propiolaldehyde; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1h;

DOI:10.1055/s-2002-33707

Reference yield:

1-ethenylcyclohexene (931-49-7) → ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate (1026853-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / diethyl ether; hexane / -40 °C

1.2: diethyl ether; hexane / 0.5 h / 20 °C

2.1: tBuOK / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 1.90 g / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; potassium tert-butylate; In diethyl ether; hexane; dichloromethane; 2.2: Wittig-Horner-Wadsworth-Emmons reaction;

DOI:10.1055/s-2002-33707

Reference yield: 63.0%

tert.-butyl lithium (594-19-4) + ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate (1026853-05-3) → ethyl 2-[(t-butoxycarbonyl)amino]-6,6-dimethyl-5-(cyclohex-1-en-1-yl)hepta-3,4-dienoate

Guidance literature:

tert.-butyl lithium; With CuCN; In diethyl ether; pentane; at -30 ℃; for 0.25h;

ethyl (Z)-2-[(t-butoxycarbonyl)amino]-5-(cyclohex-1-en-1-yl)pent-2-en-4-ynoate; In diethyl ether; pentane; at -10 ℃; for 2h;

DOI:10.1055/s-2002-33707

upstream raw materials:

3-(cyclohex-1-en-1-yl)propiolaldehyde

2-(tert-Butyloxycarbonylamino)-2-(diethoxyphosphoryl)essigsaeure-ethylester

1-ethenylcyclohexene