109-29-5Relevant articles and documents
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Mookherjee et al.
, p. 3846 (1972)
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A Simple Synthesis of trans-Δ9-Isoambrettolide, Dihydroambrettolide, and Methyl 16-Acetoxy-9-hexadecenoate
Villemin, Didier
, p. 154 - 155 (1987)
Δ9-Isoambrettolide (2) and methyl 16-acetoxy-9-hexadecenoate (3) are prepared from aleuritic acid and dimethylformamide dialkyl acetals by a one-pot reaction.Catalytic hydrogenation of products 2 and 3 affords dihydroambrettolide (6) and methyl 16-acetoxyhexadecanoate (7), respectively.
MACROCYCLIC LACTONES VIA BIOCATALYSIS IN NON-AQUEOUS MEDIA
Zhi-wei, Guo,Ngooi, T. K.,Scilimati, A.,Fuelling, Gerd,Sih, Charles J.
, p. 5583 - 5586 (1988)
The enantiospecificity of lipase-catalyzed lactonization of chiral (w-1)-hydroxy acids to form diolides in non-aqueous medium was investigated.
DMEAD: a new dialkyl azodicarboxylate for the Mitsunobu reaction
Hagiya, Kazutake,Muramoto, Natsuko,Misaki, Tomonori,Sugimura, Takashi
, p. 6109 - 6114 (2009)
Di-2-methoxyethyl azodicarboxylate (DMEAD) is prepared in 65% yield in two steps as a crystalline solid. Use of DMEAD in the Mitsunobu reaction of a variety of alcohols with pronucleophiles results in good yields of the products under sufficient stereospecificity of inversion, as conventional diisopropyl azodicarboxylate (DIAD) does. Isolation of the product is, however, much easier with DMEAD than that with DIAD, because the hydrazine produced from DMEAD is highly hydrophilic and is completely separable by a simple extraction into neutral water. Purification of the organic layer, after separation of the other by-product, triphenylphosphane oxide, by filtration, easily provides high purity of the product in a good yield. Concentration of the water layer yields the hydrazine, which can be reused for the preparation of DMEAD. One-step removal of the two by-products by the aqueous extraction was also possible when trimethylphosphane and DMEAD were employed.
Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties
Seemann, Alexandra,Panten, Johannes,Kirschning, Andreas
supporting information, p. 13924 - 13933 (2021/05/29)
Starting from small cyclic ketones, continuous flow synthesis is used to produce medium-sized rings and macrocycles that are relevant for the fragrance industry. Triperoxides are important intermediates in this process and are pyrolyzed at temperatures above 250 °C. The synthesis is carried out in two continuously operated flow reactors connected by a membrane-operated separator. The practicality of flow chemistry is impressively demonstrated in this work by the use of hazardous reagent mixtures (30% H2O2, 65% HNO3) and the pyrolysis of no less problematic peroxides. All new macrocycles were tested for their olfactory properties in relation to musk.
A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
Huy, Peter H.,Filbrich, Isabel
supporting information, p. 7410 - 7416 (2018/04/30)
A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.
