103909-86-0

Basic information

• Product Name: 3-AMINO CROTONIC ACID CINNAMYL ESTER
• Synonyms: 3-AMINO CROTONIC ACID CINNAMYL ESTER;CINNAMYL 3-AMINOCROTONATE;(E)-Cinnamyl 3-aminobut-2-enoate;3- amino -2- acid ester of maleic acid
• CAS NO: 103909-86-0
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.26
• EINECS: 1592732-453-0
• Mol File: 103909-86-0.mol

Chemical Properties

• Boiling Point: 386.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.102±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.26±0.70(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-AMINO CROTONIC ACID CINNAMYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO CROTONIC ACID CINNAMYL ESTER(103909-86-0)
• EPA Substance Registry System: 3-AMINO CROTONIC ACID CINNAMYL ESTER(103909-86-0)

Safety Data

• Hazardous Substances Data: 103909-86-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-AMINO CROTONIC ACID CINNAMYL ESTER is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the creation of complex organic molecules that can be further utilized in drug development.
Used in Fragrance and Flavor Industry:
In the fragrance and flavor industry, 3-AMINO CROTONIC ACID CINNAMYL ESTER is used as a raw material to create distinct scents and tastes, capitalizing on its characteristic odor to enhance the sensory profiles of various products.
Used in Cosmetic and Personal Care Products:
3-AMINO CROTONIC ACID CINNAMYL ESTER is used as an ingredient in cosmetic and personal care products for its potential to contribute to the formulation of creams, lotions, and other topical applications, enhancing their efficacy and sensory experience.
Used in Medicinal Chemistry and Drug Design:
In the field of medicinal chemistry and drug design, 3-AMINO CROTONIC ACID CINNAMYL ESTER is used as a building block for the development of new therapeutic agents, leveraging its chemical properties to create novel compounds with potential medicinal applications.

Upstream product

• 61363-91-5 (E)-(3-phenylallyl) 3-oxo-butyrate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 57582-46-4 cinnamyl 3-oxobutanoate 

Downstream Products

• 132203-70-4 cilnidipine 

Relevant articles and documents

Preparation method of cilnidipine

The invention relates to a preparation method of cilnidipine. The invention provides a preparation method of cinnamyl 3-aminobut-2-enoate, which comprises the following step: carrying out amination reaction on cinnamyl acetoacetate and ammonium carbonate to obtain the cinnamyl 3-aminobut-2-enoate. On the basis, the invention further provides a method for preparing cilnidipine by taking the cinnamyl 3-aminobut-2-enoate as a raw material. The method provided by the invention is relatively low in reaction temperature, relatively short in reaction time, relatively high in product yield and purity,and simple in aftertreatment.

Preparation method of 3-amino-2-butenoic acid cinnamyl ester

The invention provides a preparation method of 3-amino-2-butenoic acid cinnamyl ester, which comprises the following steps: mixing diketene with cinnamyl alcohol in a dropwise adding manner, and carrying out an esterification reaction to obtain a mixed solution containing acetoacetic acid cinnamyl ester; wherein in the process of dropwise adding the diketene, the temperature of the esterificationreaction is 30-60 DEG C. The preparation method provided by the invention is simple and feasible, the product yield is higher, the intermediate product does not need to be purified, the subsequent reaction can be directly carried out, and the method is suitable for large-scale production.

Preparation method of cilnidipine impurity or cilnidipine oxide impurity

The invention relates to a preparation process of a compound and particularly relates to a preparation method of a cilnidipine impurity or a cilnidipine oxide impurity. The preparation method of the cilnidipine impurity which is cinnamyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-diformate at least comprises a step (1) of taking cinnamyl acetyl acetate, cinnamyl 3-amino-aminocrotonateand m-nitrobenzaldehyde as raw materials, heating and reacting to obtain cinnamyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-diformate. The preparation method of the cilnidipine oxide impurity which is cinnamyl 2,6-dimethyl-4-(2-nitrophenyl)-pyridine-3,5-diformate also comprises a step (2) of oxidizing cinnamyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-diformate to obtaincinnamyl 2,6-dimethyl-4-(2-nitrophenyl)-pyridine-3,5-diformate. The preparation method is easily available in raw materials, simple and convenient to operate and easy to control; the prepared productis high in purity and is suitably used as working reference substance.

Structure-activity relationship study of 1,4-dihydropyridine derivatives blocking N-type calcium channels

Cilnidipine is a 1,4-dihydropyridine derived L/N-type calcium channel dual blocker possessing neuroprotective and analgesic effects which are related to its N-type calcium channel inhibitory activity. In order to find specific N-type calcium channel blockers with the least effects on cardiovascular system, we performed structure-activity relationship study on APJ2708, which is a derivative of cilnidipine, and found a promising N-type calcium channel blocker 21b possessing analgesic effect in vivo with a 1600-fold lower activity against L-type calcium channels than that of cilnidipine.

1,4-dihydropyridine derivatives

1,4-dihydropyridine derivatives of formula (I): STR1 wherein Ar1 and Ar2 each represent an unsubstituted or substituted aromatic hydrocarbon or aromatic heterocyclic group; and R1 represents --CO2 R2, --SO2 R3, --COR4, --CON(R5)2, --CH--or --NO2 in which R2 is hydrogen, a straight chain, branched chain or cyclic saturated hydrocarbon group, which may have a substituent or a straight chain, branched chain or cyclic unsaturated hydrocarbon group having 2 to 10 carbon atoms, which may have a substituent, R3 is an alkyl group having 1 to 4 carbon atoms, R4 is an alkyl group having 1 to 4 carbon atoms or a phenyl group; and R5 is an alkyl group having 1 to 4 carbon atoms.