Alpha-carbonyl alkenyl ester preparation method therefor and application thereof

A method for preparing an α-carbonyl alkenyl ester having the general formula (I):

• comprising the following steps:
• A) reacting the allenone having the general formula (II) with the carboxylic acid having the general formula (III) in a solvent to obtain the target compound:
• wherein R1 is selected from one of protected α-amino C1-C12 hydrocarbyl, protected β-amino C2-C20 hydrocarbyl, protected γ-amino C3-C20 hydrocarbyl, and protected polypeptide chain C1-C20 hydrocarbyl;
• R2 is selected from one of C1-C24 hydrocarbyl, C1-C24 hydrocarbyl substituted with a substituent(s), aryl, aryl substituted by a substituent(s), heteroaryl and heteroaryl substituted by a substituent(s);
• and
• R3, R4 and R5 are the same or different, and are each independently selected from one of H, C1-C18 hydrocarbyl, C1-C18 hydrocarbyl substituted by a substituent(s), C1-C16 acyl, cyano, halogen or C1-C16 hydrocarbyloxy-carbonyl.

A method for preparing the amides having the general formula (V) using α-carbonyl alkenyl ester as intermediates, comprising the following steps:

• A) reacting the α-carbonyl alkenyl ester compound having the general formula (I) and the compound having the general formula (IV) in a solvent, and optionally separating the reaction products, to obtain the target compound (V):
• wherein R1 is selected from one of protected α-amino C1-C20 hydrocarbyl, protected β-amino C2-C20 hydrocarbyl, protected γ-amino C3-C20 hydrocarbyl, and protected polypeptide chain C1-C20 hydrocarbyl;
• R2 is selected from one of C1-C24 hydrocarbyl, C1-C24 hydrocarbyl substituted by a substituent(s), aryl, aryl substituted by a substituent(s), heteroaryl and heteroaryl substituted by a substituent(s);
• R3, R4, R5 are the same or different, and are each independently selected from one of H, C1-C18 hydrocarbyl, C1-C18 hydrocarbyl substituted by a substituent(s), C1-C16 acyl, cyano, halogen or C1-C16 hydrocarbyloxy-carbonyl;
• and
• R6 and R7 are each independently selected from one of H, amino, C1-C24 hydrocarbyl, C1-C24 hydrocarbyl substituted by a substituent(s), or amino oligomers or amino polymers with primary and/or secondary amine group(s);
• or, R6 and R7 together with the N atom to which they are attached form a C3-C24 cyclic ring.

A method for preparing an amide having the general formula (V), comprising:

• A) reacting the allenone compound having the general formula (II) with the carboxylic acid having the general formula (III) in a first solvent, optionally separating the reaction product, and then obtaining the α-carbonylalkenyl ester;
• and
• B) reacting the α-carbonylalkenyl ester prepared in step A) with a compound having general formula (IV) in a second solvent, optionally separating the reaction product, to obtain an amide having the general formula (V):
• wherein R1 is selected from one of protected α-amino C1-C20 hydrocarbyl, protected β-amino C2-C20 hydrocarbyl, protected γ-amino C3-C20 hydrocarbyl, and protected polypeptide chain C1-C20 hydrocarbyl;
• R2 is selected from one of C1-C24 hydrocarbyl, C1-C24 hydrocarbyl substituted by a substituent(s), aryl, aryl substituted by a substituent(s), heteroaryl and heteroaryl substituted by a substituent(s);
• R3, R4, R5 are the same or different, and are each independently selected from one of H, C1-C18 hydrocarbyl, C1-C18 hydrocarbyl substituted by a substituent(s), C1-C16 acyl, cyano, halogen or C1-C16 hydrocarbyloxy-carbonyl;
• and
• R6 and R7 are each independently selected from one of H, amino, C1-C24 hydrocarbyl, C1-C24 hydrocarbyl substituted by a substituent(s), or amino oligomers or amino polymers with primary and/or secondary amines;
• or, R6 and R7 together with the N atom to which they are attached form a C3-C24 cyclic ring;
• wherein the first solvent is the same or different from the second solvent.