58885-60-2Relevant articles and documents
Self-Assembly of C3 Symmetric Rigid Macrolactams into Very Polar and Porous Trigonal Crystals
Marmin, Thomas,Dory, Yves L.
, p. 6707 - 6711 (2019)
Cyclohexane and cyclotri-β-alanyl have been used as scaffolds for the design of new C3-symmetric rings incorporating conjugated alkenes and dienes. All three C3-symmetric lactams share the same triangular shape and their crystal system is trigonal. They all belong to the R3 space group, R3m, R3 and R3c, for the increasingly large 12-, 18- and 24-membered rigid rings, respectively. All lactams stack on top of each other, through H-bonds and van der Waals noncovalent interactions, leading to endless supramolecular cylinders and tubes. The largest member of the family leads to tubes, the central pores of which is wide enough to let water in. A common feature of all the lactams is their very large dipole, of around 9 D, according to DFT calculations. Surprisingly, all the resulting cylinders and tubes pack side by side in the crystals, with all the dipoles pointing to the same direction. As a result, all three crystals are anisotropic and appear to be the first members of a new kind of highly polar crystals.
Asymmetric total synthesis of novel pentacyclic indole alkaloid, kopsiyunnanine E, isolated from Kopsia arborea
Kitajima, Mariko,Murakami, Yosuke,Takahashi, Nobuaki,Wu, Yuqiu,Kogure, Noriyuki,Zhang, Rong-Ping,Takayama, Hiromitsu
, p. 5000 - 5003 (2014)
A new pentacyclic indole alkaloid, kopsiyunnanine E, was isolated from Yunnan Kopsia arborea, and its structure, which was inferred from spectroscopic data, was established by a 16-step asymmetric total synthesis that proved that the natural alkaloid was not enantiomerically pure.
Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
Lorton, Charlotte,Saleh, Nidal,Voituriez, Arnaud
, p. 3340 - 3344 (2021/06/26)
Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.
Novel method for synthesizing 2-(1-methylimidazole-5-yl) ethylamine hydrochloride
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, (2021/04/28)
The invention discloses a novel method for synthesizing 2-(1-methylimidazole-5-yl) ethylamine hydrochloride, which comprises the following steps: 1, reacting 3-amino propanol serving as an initial raw material with di-tert-butyl dicarbonate to obtain 3-(Boc-amino) propanol; 2, carrying out Swen oxidation reaction: carrying out Swen oxidation on the obtained 3-(Boc-amino) propanol to obtain 3-(Boc-amino) propionaldehyde; 3, cyclization reaction: reacting the obtained 3-(Boc-amino) propionaldehyde with a methylamine methanol solution to generate Schiff base, and directly carrying out Van Lessel reaction on the Schiff base and p-toluenesulfonyl methyl isocyanide without separation to synthesize 2-(1-methyl-1H-imidazole-5-yl) tert-butyl ethylcarbamate; and 4, reacting the obtained 2-(1-methyl-1H-imidazole-5-yl) tert-butyl ethylcarbamate with a hydrogen chloride isopropanol solution to remove Boc, thereby obtaining the final product 2-(1-methylimidazole-5-yl) ethylamine hydrochloride. The method has the beneficial effects that the method is prepared from cheap raw materials which are easy to obtain, the reaction yield is high, the total steps are few, the operation is simple, the production cost is low, and industrialization is easy to realize.
