41302-34-5Relevant academic research and scientific papers
Carboxylation of cyclohexanone with carbon dioxide and potassium phenoxide. Dependence of the reaction upon the amount of carbon dioxide complexed with potassium phenoxide
Mori,Satake
, p. 3469 - 3472 (1985)
The uptake of CO2 by potassium phenoxide (PhOK) in N,N-dimethylformamide (DMF) was investigated in a vacuum system. Further, the carboxylation of cyclohexanone by various amounts of CO2 complexed with PhOK was studied. The yield of the carboxylate at 30s increased with increase of M.R. (molar ratio of CO2 absorbed by PhOK to PhOK initially added) in the range of M.R. less than 0.41. However, in the range of M.R. above 0.60, it decreased with increase of M.R. The time required for completion of the reaction depended on the M.R., and the three ranges were distinguishable. The ultimate yield of the carboxylate in the carboxylation increased proportionally to M.R. value. It is considered that the source of CO2 for carboxylate formation was CO2 complexed with PhOK rather than uncomplexed CO2.
Efficient and reusable PdCl2(MeCN)2/CuCl 2/PEG-400 system for cyclization of alkenyl β-keto esters and amides
Li, Jin-Heng,Zhu, Qi-Ming,Liang, Yun,Yang, Dan
, p. 5347 - 5349 (2005)
PEG-400 [poly(ethylene glycol-400)] was found as an effective medium for the PdCl2(MeCN)2-catalyzed hydroalkylation cyclization of alkenyl β-keto esters and amides. In PEG-400, no additives such as Me 3SiCl and Ln(OTf)3 were required for the complete conversion of alkenyl β-keto esters. The results also snowed that CuCl 2 could promote the reaction. In the presence of PdCl 2(MeCN)2, CuCl2, and PEG-400, various alkenyl β-keto esters and amides underwent a selective cyclization reaction to give good to excellent yields of the desired six-membered-ring carbocycles. Furthermore, the PdCl2(MeCN)2/CuCl2/PEG-400 system could be recycled and reused five times without any loss of catalytic activity.
An improved synthesis of a hydroxymethyl tricyclic ketone from cyclohexanone, the key processes for the synthesis of a highly potent anti-inflammatory and cytoprotective agent
Saito, Akira,Zheng, Suqing,Takahashi, Motohiro,Li, Wei,Ojima, Iwao,Honda, Tadashi
, p. 3251 - 3254 (2013)
An improved synthesis of hydroxymethyl tricyclic ketone, (±)-(4aS,8aS)-8a-(hydroxymethyl)-1,1,4a-trimethyl-3,4,4a,6,7,8,8a,9,10, 10a-decahydrophenanthren-2(1H)-one, in five steps (34% yield) from cyclohexanone has been successfully established. Accordingly, 10 grams of a highly potent anti-inflammatory and cytoprotective agent, (±)-(4bS,8aR,10aS)-10a- ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octahydrophenanthrene-2, 6-dicarbonitrile (TBE-31), was obtained in 15 steps (9.2% overall yield) via the hydroxymethyl tricyclic ketone from 32 grams of cyclohexanone. Georg Thieme Verlag Stuttgart New York.
Highly Selective Difluoromethylations of β-Keto Amides with -TMSCF 2Br under Mild Conditions
Chen, Pengli,Fu, Yang,Hu, Yanqin,Wang, Shuaifei,Wang, Yakun,Zhang, Conghui,Zhang, Mingwei,Zhao, Ting
supporting information, p. 1123 - 1130 (2021/06/18)
Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF 2 Br reagent have been developed under mild conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high carbon/oxygen (C/O) regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled-up and the C-difluoromethylation product could be reduced into CF 2 H-containing amino alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis.
Novel BCL-2/BCL-XL inhibitor, pharmaceutical composition and application
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Paragraph 0045-0048; 0050-0051, (2020/11/12)
The invention relates to a compound for inhibiting the activity of Bcl-2/BCL-XL anti-apoptotic protein, a composition containing the compound and application of the compound serving as a synthetic drug, in particular to application of the compound serving as a drug for synthesizing a Bcl-2/BCL-XL anti-apoptotic protein inhibitor and application of the compound to cancer.
INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
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Paragraph 0274, (2020/01/24)
The present invention relates to compounds that have the ability to inhibit lysine biosynthesis via the diaminopimelate pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful. Applications of this type include the use of the compound as herbicides and/or anti-bacterial agents.
Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides
Rao, M.V. Krishna,Reddy, K. Nagarjuna,Sridhar,Reddy, B.V. Subba
supporting information, (2019/09/16)
α-Sulfonamidation of β-ketoesters with sulfonyl azide has been developed for the first time using a catalytic amount of Ru(II) complex to produce the 1-oxo-2-(sulfonamido)-2,3-dihydro-1H-indene-2-carboxylate and 1-oxo-2-(sulfonamido)-1,2,3,4-tetrahydronaphthalene-2-carboxylate derivatives in good yields. This method also works well with α-iodotetralones to afford the N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulphonamide derivatives under similar conditions.
Enantioselective Palladium-Catalyzed Decarboxylative Allylation of β-Keto Esters Assisted by a Thiourea
Qian, Hua,Gu, Guoxian,Zhou, Qinghai,Lu, Jiaxiang,Chung, Lung Wa,Zhang, Xumu
supporting information, p. 51 - 56 (2017/10/06)
Enantioselective intramolecular decarboxylative allylation of β-keto esters catalyzed by a palladium bis(phosphine)-thiourea complex is reported. This procedure is not only effective for β-keto esters, but also effective for β-keto amides. An intermolecular variant of the asymmetric decarboxylative allylation is also established. DFT calculations indicate that an outer-sphere mechanism is viable for the decarboxylative allylation of β-keto esters.
Novel KV7 ion channel openers for the treatment of epilepsy and implications for detrusor tissue contraction
Seefeld, Mark A.,Lin, Hong,Holenz, Joerg,Downie, Dave,Donovan, Brian,Fu, Tingting,Pasikanti, Kishore,Zhen, Wei,Cato, Matthew,Chaudhary, Khuram W.,Brady, Pat,Bakshi, Tania,Morrow, Dwight,Rajagopal, Sridharan,Samanta, Swapan Kumar,Madhyastha, Naveena,Kuppusamy, Bharathi Mohan,Dougherty, Robert W.,Bhamidipati, Ravi,Mohd, Zainuddin,Higgins, Guy A.,Chapman, Mark,Rouget, Céline,Lluel, Philippe,Matsuoka, Yasuji
supporting information, p. 3793 - 3797 (2018/10/20)
Neuronal voltage-gated potassium channels, KV7s, are the molecular mediators of the M current and regulate membrane excitability in the central and peripheral neuronal systems. Herein, we report novel small molecule KV7 openers that demonstrate anti-seizure activities in electroshock and pentylenetetrazol-induced seizure models without influencing Rotarod readouts in mice. The anti-seizure activity was determined to be proportional to the unbound concentration in the brain. KV7 channels are also expressed in the bladder smooth muscle (detrusor) and activation of these channels may cause localized undesired effects. Therefore, the impact of individual KV7 isoforms was investigated in human detrusor tissue using a panel of KV7 openers with distinct activity profiles among KV7 isoforms. KCNQ4 and KCNQ5 mRNA were highly expressed in detrusor tissue, yet a compound that has significantly reduced activity on homomeric KV7.4 did not reduce detrusor contraction. This may suggest that the homomeric KV7.4 channel plays a less significant role in bladder contraction and further investigation is needed.
Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award
Boumediene, Mehdi,Guignard, Rapha?l F.,Zard, Samir Z.
, p. 3678 - 3686 (2016/06/06)
Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.
