632-02-0Relevant articles and documents
Preparation method of optically active N-(halogenated propyl) amino acid derivative
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Paragraph 0061-0063, (2021/08/14)
The invention provides a preparation method of an optically active N-(halogenated propyl) amino acid derivative, namely the N-(halogenated propyl) amino acid derivative represented by a formula (I) is obtained by reacting an optically active alanine ester
An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols
Zinin,Stepanova,Jost,Kondakov,Shpirt,Chizhov,Torgov,Kononov
, p. 304 - 312 (2017/07/11)
Efficient multigram two-step syntheses of 4-(2-chloroethoxy)phenol and 4-(3-chloropropoxy)phenol in >70% yields starting from 4-hydroxybenzaldehyde and reagents with general formula Cl(CH2)nX (X = Cl, n = 2; X = OTs, n = 3) are proposed. 4-(2-Chloroethoxy)phenol can also be conveniently prepared from 4-methoxyphenol and 1,2-dichloroethane. The compounds thus obtained can be used in carbohydrate chemistry to synthesize glycosides bearing "universal" 4-(ω-chloroalkoxy)phenyl aglycons.
Development and Kilogram-Scale Synthesis of a D2/5-HT2A Receptor Dual Antagonist (±)-SIPI 6360
Chen, Xiao-Wen,Liu, Yu,Jin, Xun-Qi,Sun, Yuan-Yuan,Gu, Shun-Lin,Fu, Lei,Li, Jian-Qi
, p. 1662 - 1667 (2016/09/23)
The kilogram-scale synthesis of a D2/5-HT2A receptor dual antagonist (±)-SIPI 6360 was developed as an alternative treatment for schizophrenia. Specifically, three conditions were modified and optimized, including the Vilsmeier condi
Membrane-targeting dcap analogues with broad-spectrum antibiotic activity against pathogenic bacteria
Hurley, Katherine A.,Heinrich, Victoria A.,Hershfield, Jeremy R.,Demons, Samandra T.,Weibel, Douglas B.
supporting information, p. 466 - 471 (2015/04/27)
We performed a structure-activity relationship study of 2-((3-(3,6-dichloro-9H-carbazol-9-yl)-2-hydroxypropyl)amino)-2-(hydroxymethyl)propane-1,3-diol (DCAP), which is an antibacterial agent that disrupts the membrane potential and permeability of bacteri
Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth
Taguri, Tomonori,Yamakawa, Rei,Adachi, Yasushi,Mori, Kenji,Ando, Tetsu
experimental part, p. 119 - 124 (2010/04/26)
Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce a novel sex pheromone composed of three methyl-branched ketones: 6-methyl-2-octade-canone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). Their structures were confirmed by syntheses accomplished by a different route for each component. In order to obtain a sufficient amount of the synthetic pheromone, we developed new routes via methyl-branched 1-alkenes: 6-methyl-l-octa-decene (1), 14-methyl-l-octadecene (2), and 6,14-di-methyl-1-octadecene (3). Compound 1 was synthesized by coupling between a C10-chain bromide and a 3-methyl-branched C8 unit (A) prepared from 3-methyl-1,5-pentanediol, 2, by coupling between a C 11-chain bromide and a 3-methyl-branched C7 unit (B) prepared from 2-hexanone, and 3, by connecting A and B, using propargyl alcohol as a C3 linchpin. The use of 3-chloro-1-propanol and tert-butyl acetoacetate as the linchpin was also examined to connect the two synthetic blocks in the synthesis of 3. Components I-III were obtained by Wacker oxidation of the corresponding 1-alkenes 1-3 in good yields.
New syntheses of 1,7-dimethylnonyl propanoate, the western corn rootworm pheromone, in four different ways via cross metathesis, alkylation and coupling reactionsss
Mori, Kenji
experimental part, p. 595 - 600 (2011/04/23)
A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an alkynide anion, and (iv) Grignard coupling in the presence of dilithium tetrachlorocuprate. Although the cross metathesis approaches enabled two short syntheses (4 or 6 steps) of the pheromone to be achieved, the cheapest and most efficient synthesis was possible via Grignard coupling to give the desired pheromone in a 40% overall yield based on 2-methyl-1-butanol (8 steps).
Nitrogenous macrocyclic compounds
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, (2011/08/10)
PCT No. PCT/US96/04215 Sec. 371 Date Sep. 19, 1997 Sec. 102(e) Date Sep. 19, 1997 PCT Filed Mar. 27, 1996 PCT Pub. No. WO96/30377 PCT Pub. Date Oct. 3, 1996Novel macrocyclic compounds are constructed to include large cyclic structures that are interrupted by at least one ring system. Each interrupting ring system includes two bridgehead atoms. Bridgehead atoms are bonded to one or more bridges that interconnect one or more ring systems thereby forming a large cyclic structure. Located in each bridge are two or more nitrogenous moieties that are derivatized with chemical functional groups. The ring systems can include further nitrogenous moieties, either as ring atoms or on pendant groups attached to the ring. These can also be derivatized with chemical functional groups. The totality of the chemical functional groups imparts certain conformational and other properties to the macrocyclic compounds. In accordance with certain embodiments of the invention, libraries of such macrocyclic compounds are prepared utilizing permutations and combinations of the chemical functional groups and the nitrogenous moieties to build complexity into the library.
Use of organoboranes in the synthesis of pheromones: A convenient synthesis of (Z)-6-heneicosen-11-one and (Z)-5-undecen-2-one, pheromones from the Douglas Fir Tussock Moth and the Bontebok, respectively
White,Whiteley
, p. 1141 - 1144 (2007/10/02)
Treatment of thexylborane with a halomagnesiumdialkylcuprate afforded the corresponding (R-alkyl)thexylborane in favourable yields. A second reaction with a halomagnesiumdialkenylcuprate produced the totally mixed (R-alkyl)(E-alkenyl)thexylborane. Subsequent treatment with sodium cyanide and benzoyl chloride followed by alkaline peroxide yielded an unsaturated ketone. In this way, (Z)-6-heneicosen-11-one, a sex pheromone of the Douglas Fir Tussock Moth, and (Z)-5-undecen-2-one, a pheromone from the pedal gland of the Bontebok, were prepared.
Synthesis of a New P2N2 Ligand N,N'-Bispropane-1,3-diamine, H2L2, and some of its Complexes with Elements of the Nickel Triad and Rhodium: X-Ray Structure Analyses of the Neutral Complex 2> and the tr
Cooper, Mervyn K.,Duckworth, Paul A.,Hambley, Trevor W.,Organ, Gregory J.,Henrick, Kim,et al.
, p. 1067 - 1074 (2007/10/02)
The new multidentate phosphorus-nitrogen P2N2 hybride ligand N,N'-bispropane-1,3-diamine, H2L2, has been prepared by demetallation of its neutral deprotonated nickel complex 2>, (1a), obtained from th