Copper(I) acetylide (Cu2C2) is a reddish, explosive solid, produced by passing acetylene through copper(I) chloride solution.
Carbodiimide 1 reacts with acyl chloride 3 to generate N-acylimide salt 5. Alkyne 2 is immediately converted to acetylide copper 4 in the presence of triethylamine, and 1 equivalent of triethylamine acid salt is released. Subsequently, 4 undergoes nucleophilic attack on 5 to obtain the target product 6, and the copper catalyst is released, completing the catalytic cycle.
Cavicularin is a complex natural product isolated from the liverwort Cavicularia densa. It belongs to the class of macrocyclic bis(bibenzyl) compounds and features a unique, strained 14-membered macrocyclic ether ring incorporating two ethano bridges and multiple hydroxyl groups.
Synthetic strategy to cavicularin (1).
Total synthesis of cavicularin (1) and riccardin C (20). Ts =p-toluenesulfonyl, TTMSS=tris(trimethylsilyl)silane, AIBN=azo-bis(isobutyronitrile).
5-Phenyl-1H-tetrazole is a heterocyclic compound characterized by a phenyl group attached to a tetrazole ring. It's a white to light beige powder.
Thermolysis of 5-Phenyltetrazole
Photolysis of 5-Phenyltetrazole 2
IR difference spectrum after 1 min photolysis (254 nm) of 5-phenyltetrazole 2 in Ar matrix at 12 K. Positive peaks: photolysis products, largely benzonitrile imine 6; the peak near 1700 cm−1 is due to an impurity on the deposition window. Negative peaks: reacted tetrazole 2.
(Left) Partial IR difference spectra of 5-phenyltetrazole 2 at 12 K in Ar matrix at different photolysis times, showing peaks due to the photolysis products. Peaks at 2129 and 2166 cm−1 are due to PhN=C=NH 5. The peak at 2073 cm−1 is assigned to PhCNNH 6. Ordinate in absorbance units. (Right) Plots of IR absorbances at different wavelengths versus photolysis time. Ordinate in relative absorbance units.
Cerasonine is a natural product that has been isolated from the stem bark of the plant Polyalthia cerasoides. It belongs to a class of compounds called oxoprotoberberine alkaloids.
Structure of the Protoberberine Alkaloid, Cerasonine
(2E)-3-Phenyl-2-propenenitrile, also known as cinnamonitrile or (E)-cinnamyl nitrile. Structurally, it consists of a phenyl group (C₆H₅–) attached to a propenenitrile chain (CH=CH–CN), where the double bond between the second and third carbon atoms is in the E (trans) configuration. This gives the molecule a linear geometry across the double bond, contributing to its stability and unique chemical reactivity. It appears as a colorless to pale yellow liquid and is used primarily as an intermediate in organic synthesis, including the production of pharmaceuticals, agrochemicals, and fragrances. Its nitrile group contributes to moderate polarity and can participate in various chemical transformations such as reduction, hydrolysis, or cyclization.
Biotransformation of cinnamonitrile using E. coli JM101 (pTEZ30) in shake flasks. Reaction was performed usingrestingcells (1.29 gcdw/L) in 20-mL shake flasks.
Biotransformation of cinnamonitrile using E. coli JM101 (pTEZ30) in a bioreactor on a 2-L scale.
Biotransformation of cinnamonitrile using E. coli JM101 (pTEZ30) in a bioreactor with a 30-L workingvol-ume.
Volumetric productivities of biotransformation of cinnamonitrile using E. coli JM101 (pTEZ30) in shake-flasks, and in reactors on 2-L and 30-L scales, and the specific growth rate of the cells in a 30-L reactor.