 | |
| Names | |
|---|---|
| Preferred IUPAC name 3-(Dibutylamino)propyl 4-aminobenzoate | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.214 |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
| |
| Properties | |
| C18H30N2O2 | |
| Molar mass | 306.450 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Butacaine is a white crystalline ester used as a local anesthetic. [1] It was first marketed in 1920. [1]
The addition of metallic sodium is added to a mixture of allyl alcohol (1) and dibutylamine (2) [2] gives the conjugate addition product 3-dibutylamino-1-propanol (3). Esterification of this intermediate with para-nitrobenzoyl chloride (4) gives the ester 5. The reduction of the nitro group completes the synthesis of butacaine (6). [3] [4] [5] [6] [7] [8]
The aldol reaction is a reaction in organic chemistry that combines two carbonyl compounds to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step. As such, there is no obvious retron for this reaction. The reaction was reported by Nikolai Kischner in 1911 and Ludwig Wolff in 1912.
The Claisen rearrangement is a powerful carbon–carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to give a γ,δ-unsaturated carbonyl, driven by exergonically favored carbonyl CO bond formation (Δ = −327 kcal/mol.
Adams' catalyst, also known as platinum dioxide, is usually represented as platinum(IV) oxide hydrate, PtO2•H2O. It is a catalyst for hydrogenation and hydrogenolysis in organic synthesis. This dark brown powder is commercially available. The oxide itself is not an active catalyst, but it becomes active after exposure to hydrogen whereupon it converts to platinum black, which is responsible for reactions.
The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.
Ernest Henry Volwiler was an American chemist. He spent his career at Abbott Laboratories working his way from staff chemist to CEO. He was a pioneer in the field of anesthetic pharmacology, assisting in the development of two breakthrough drugs, Nembutal and Pentothal. Volwiler also helped Abbott Laboratories to achieve commercial success for its pharmaceutical products including the commercialization of penicillin and sulfa drugs during World War II.
Roger Adams was an American organic chemist who developed the eponymous Adams' catalyst, and helped determine the composition of natural substances such as complex vegetable oils and plant alkaloids. He isolated and identified CBD in 1940. As head of the Chemistry department at the University of Illinois from 1926 to 1954, he influenced graduate education in America, taught over 250 Ph.D. students and postgraduate students, and served in military science during World War I and World War II.
Butamben is a local anesthetic. Proprietary names includes Alvogil in Spain and Alvogyl in Switzerland. It is one of three components in the topical anesthetic Cetacaine.
A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.
Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.
Cycloguanil is a dihydrofolate reductase inhibitor, and is a metabolite of the antimalarial drug proguanil; its formation in vivo has been thought to be primarily responsible for the antimalarial activity of proguanil. However, more recent work has indicated that, while proguanil is synergistic with the drug atovaquone, cycloguanil is in fact antagonistic to the effects of atovaquone, suggesting that, unlike cycloguanil, proguanil may have an alternative mechanism of antimalarial action besides dihydrofolate reductase inhibition.
Selenoxide elimination is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. It is mechanistically related to the Cope reaction.
Basketane is a polycyclic alkane with the chemical formula C10H12. The name is taken from its structural similarity to a basket shape. Basketane was first synthesized in 1966, independently by Masamune and Dauben and Whalen. A patent application published in 1988 used basketane, which is a hydrocarbon, as a source material in doping thin diamond layers because of the molecule's high vapor pressure, carbon ring structure, and fewer hydrogen-to-carbon bond ratio.
The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction. This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory University, Atlanta, Georgia, USA. There are three generations of this reaction, with the first generation shown below. The original transformation used catalytic Pd(0), TFP = tris(2-furyl)phosphine as an additional ligand and stoichiometric CuTC = copper(I) thiophene-2-carboxylate as a co-metal catalyst. The overall reaction scheme is shown below.
Metal carbon dioxide complexes are coordination complexes that contain carbon dioxide ligands. Aside from the fundamental interest in the coordination chemistry of simple molecules, studies in this field are motivated by the possibility that transition metals might catalyze useful transformations of CO2. This research is relevant both to organic synthesis and to the production of "solar fuels" that would avoid the use of petroleum-based fuels.
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. It was first described by Eduard Buchner and Theodor Curtius in 1885 and later by Fritz Schlotterbeck in 1907. Two German chemists also preceded Schlotterbeck in discovery of the reaction, Hans von Pechmann in 1895 and Viktor Meyer in 1905. The reaction has since been extended to the synthesis of β-keto esters from the condensation between aldehydes and diazo esters. The general reaction scheme is as follows:
In organic chemistry, carbonyl allylation describes methods for adding an allyl anion to an aldehyde or ketone to produce a homoallylic alcohol. The carbonyl allylation was first reported in 1876 by Alexander Zaitsev and employed an allylzinc reagent.
Peter Wipf is a distinguished university professor of chemistry at the University of Pittsburgh. His research interests focus on the total synthesis of natural products, the discovery of new transformations of strained molecules, and the development of new pharmaceuticals. He is a Fellow of the Royal Society of Chemistry (RSC), the American Association for the Advancement of Science (AAAS), and the American Chemical Society (ACS).
1,3-Diphenylisobenzofuran is a highly reactive diene that can scavenge unstable and short-lived dienophiles in a Diels-Alder reaction. It is furthermore used as a standard reagent for the determination of singlet oxygen, even in biological systems. Cycloadditions with 1,3-diphenylisobenzofuran and subsequent oxygen cleavage provide access to a variety of polyaromatics.
