33106-64-8Relevant articles and documents
Synthesis of a new asymmetric cyclopentadienyl ligand: application to the preparation of a trivalent samarium complex
Weghe, P. Van de,Bied, C.,Collin, J.,Marcalo, J.,Santos, I.
, p. 121 - 126 (1994)
A short synthesis of a new asymmetric cyclopentadienyl ligand 2 (Cp'H) substituted by a benzyl ether group in the β position on the side chain of the ring is described.Reaction of its potassium salt with samarium triiodide leads to the isolation of a triv
Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines
Moore, Lucas C.,Lo, Anna,Fell, Jason S.,Duong, Matthew R.,Moreno, Jose A.,Rich, Barry E.,Bravo, Martin,Fettinger, James C.,Souza, Lucas W.,Olmstead, Marilyn M.,Houk, Kendall N.,Shaw, Jared T.
, p. 12214 - 12220 (2019)
Diastereoselective Lewis acid-mediated additions of nucleophilic alkenes to N-sulfonyl imines are reported. The canonical polar Felkin–Anh model describing additions to carbonyls does not adequately describe analogous additions to N-sulfonyl imines. Herei
Preparation of Optically Active (S)-2-(Benzyloxy)propanal
Varelis, Peter,Johnson, Brian L.
, p. 1775 - 1780 (1995)
A convenient and large scale amenable preparation of optically active ethyl (S)-2-(benzyloxy)propionate (5) from ethyl (S)-lactate (4), and the conversion of the ester (5) by two alternative methods into (S)-2-(benzyloxy)propanal (1) are described.
6-HETEROARYLOXY BENZIMIDAZOLES AND AZABENZIMIDAZOLES AS JAK2 INHIBITORS
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Paragraph 0954; 0956, (2021/11/13)
The present disclosure provides 6-heteroaryloxy benzimidazole and azabenzimidazole compounds and compositions thereof useful for inhibiting JAK2.
Benzoxaborole Catalyst for Site-Selective Modification of Polyols
Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
supporting information, p. 1598 - 1602 (2020/02/11)
The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system
Lv, Jian,Liu, Yu,Zhu, Jia-Jia,Zou, Dapeng,Dong, Hai
supporting information, p. 1139 - 1144 (2020/03/11)
In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.
COMPOUNDS FOR USE IN THE TREATMENT OR PROPHYLAXIS OF PAIN, INFLAMMATION AND/OR AUTOIMMUNITY
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Page/Page column 15-16, (2020/08/13)
The present invention relates to a polymorphic form of (S,S)-2-N(3-O-(propan-2-ol)-1-propyl- 4-hydroxybenzene)-3-phenylpropylamide or synonymously named N-[2-(4-Hydroxy-phenyl)- -(2-hydroxy-propoxymethyl)-ethyl]-3-phenyl-propionamide and to the treatment
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors
Nakamura, Sho,Sayama, Misa,Uwamizu, Akiharu,Jung, Sejin,Ikubo, Masaya,Otani, Yuko,Kano, Kuniyuki,Omi, Jumpei,Inoue, Asuka,Aoki, Junken,Ohwada, Tomohiko
, p. 9990 - 10029 (2020/10/18)
Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of l-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure-activity relationship studies of more than 100 "glycol surrogate"derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1-and 2-acyl lysophospholipids.
A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes
Banerjee, Ankush,Maji, Modhu Sudan
supporting information, p. 11521 - 11527 (2019/08/16)
A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.
C -Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts
Siddiki, S. M. A. Hakim,Touchy, Abeda S.,Jamil, Md. A. R.,Toyao, Takashi,Shimizu, Ken-Ichi
, p. 3091 - 3103 (2018/04/14)
A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.
