35071-67-1Relevant academic research and scientific papers
Method for manufacturing substituted cyclopentadiene
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Paragraph 0057-0061, (2021/11/24)
The present invention relates to a method for producing substituted cyclopentadiene using a strong base and an ether solvent having a high boiling point. Using this method, economical mass production of high purity alkyl substituted cyclopentadiene is possible.
Method for preparing gamma-thujaplicin by applying simulated moving bed chromatography
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Paragraph 0036; 0064; 0065; 0066; 0067, (2018/12/13)
The invention relates to a method for preparing gamma-thujaplicin by applying simulated moving bed chromatography. The method comprises the following steps: generating potassium cyclopentadiene by using cyclopentadiene and potassium hydroxide, carrying out a reaction between potassium cyclopentadiene and isopropyl bromide and heating under the condition of strong alkali and weak acid salt to prepare 2-isopropylcyclopentadiene; performing addition a reaction product of dichloracetyl chloride and triethylamine as well as 2-isopropylcyclopentadiene to prepare 2-isopropylcyclopentadiene ethenone addition product, and performing ring expansion reaction to synthesize a crude product of gamma-thujaplicin; applying a simulated moving bed chromatographic system to separate a crude product of the gamma-thujaplicin and applying a simulated moving bed to purify the gamma-thujaplicin, wherein the total yield of the gamma-thujaplicin is more than 60.0 percent and the purity is more than 97.0 percent. The method has the advantages of simple process, simple and convenient reaction condition, low cost, high yield and capability of meeting the environmental protection requirement.
A high-purity chinese juniper methyl alcohol of preparation method (by machine translation)
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Paragraph 0020; 0021; 0025; 0027; 0029; 0031; 0033; 0035, (2018/08/03)
The invention discloses a method for preparing high-purity chinese juniper methyl alcohol, cyclopentadiene activated reagent after activation with isopropyl bromine instead should be containing various isomers of the isopropyl cyclopentadiene, then in the isomer conversion catalyst under the action of the isomerization reaction to obtain 1 - isopropyl cyclopentadiene; 1 - isopropyl cyclopentadiene and [...] react 1 - isopropyl cyclopentadiene and 4, 4 - [...] 5 - one; 1 - isopropyl cyclopentadiene and 4, 4 - [...] 5 - ketone with triethylamine heating reflux generating ring enlargement reaction to obtain the target product chinese juniper methyl alcohol. The invention raw materials used are cheap and easily obtained, and the step A through the isomer of a hydrocarbon conversion catalyst in use significantly reduces the by-product 2 - isopropyl cyclopentadiene and 5 - isopropyl cyclopentadiene generation, improves the yield of products, and Ru (Ac)3 - ZSM - 5 can be repeatedly used for four times still maintains good catalytic activity; step B by adjusting reaction solution in glacial acetic acid, effectively prevent the emergence of the diketone by-product. (by machine translation)
Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde
Hatano, Manabu,Sakamoto, Tatsuhiro,Mizuno, Tomokazu,Goto, Yuta,Ishihara, Kazuaki
supporting information, p. 16253 - 16263 (2018/11/27)
The Diels-Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon-carbon bond formations, is one of the most powerful tools to synthesize versatile and unique six-membered rings. We show that chiral supramolecular U-shaped boron Lewis acid catalysts promote the unprecedented multiselective Diels-Alder reaction of propargyl aldehyde with cyclic dienes. Independent from the substrate control, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivities could be controlled by the present U-shaped catalysts. The obtained reaction products could access the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin. The results presented here might partially contribute to the development of artificial enzyme-like supramolecular catalysts for multiselective reactions, which will be able to target organic compounds that have thus far eluded synthesis.
A six-step total synthesis of α-thujone and: D 6-α-thujone, enabling facile access to isotopically labelled metabolites
Thamm, Irene,Richers, Johannes,Rychlik, Michael,Tiefenbacher, Konrad
supporting information, p. 11701 - 11703 (2016/10/04)
The short synthesis of α-thujone relies on the functionalization of the readily available dimethylfulvene. Furthermore, the three main metabolites of the natural product were also synthesized. Since d6-acetone can be used as a starting material, the route developed allows for the facile incorporation of isotopic labels which are required for detecting and quantifying trace amounts via GC/MS analysis.
REDUCTION OF 6,6-DISUBSTITUTED FULVENES WITH ALKALI METALS
Koshchutin, V. I.,Levchenko, V. M.,Koshchutina, L. L.
, p. 47 - 53 (2007/10/02)
Irrespective of the nature of the alkali metals and the solvent, the reduction of 6,6-disubstituted fulvenes with alkali metals is fairly selective and occurs at the exocyclic double bond to form substituted cyclopentadienes.The mechanism of such reactions is discussed.
