104-52-9Relevant articles and documents
An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2
Pluempanupat, Wanchai,Chavasiri, Warinthorn
, p. 6821 - 6823 (2006)
A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.
Remarkable interaction effects of molecular packing on site- and stereoselectivity in photocycloaddition of 2-pyrones with maleimide in the solid state
Obata, Toru,Shimo, Tetsuro,Yasutake, Mikio,Shinmyozu, Teruo,Kawaminami, Masaru,Yoshida, Ryosuke,Somekawa, Kenichi
, p. 1531 - 1541 (2001)
Solid-state photoirradiation of 1:1 complex crystals of 4-[ω-(2-furyl)alkyloxy]-6-methyl-2-pyrones 1b, 1c or 4-(ω-arylalkyloxy)-6-methyl-2-pyrones 1d-j with maleimide 2 gave [2+2]cycloadducts 3b-f, 3i, 3j with exclusive stereoselectivity. The high reaction selectivity was confirmed by X-ray structure analyses and MO method of the complex crystals, which were composed of two sets of a 1:1 complex between 1 and 2, arising from an CH-π interaction between 2 and the aromatic rings of 1, and/or π-π stacking between the aromatic rings in addition to four kinds of hydrogen bonding between the ground state 2-pyrone moieties and 2.
Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 8059 - 8064 (2020)
While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Preparation method of 3-phenylpropylamine
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Page/Page column 4-6, (2019/10/08)
The embodiment of the invention discloses a preparation method of 3-phenylpropylamine. The method comprises the following steps: 2-(3-phenylpropyl)isoindoline-1,3-diketone is obtained through 1-chloro-3-phenylpropane under the action of a phthalimide salt compound and a base; then the 2-(3-phenylpropyl)isoindoline-1,3-diketone is subjected to hydrazinolysis through hydrazine hydrate; after alkalization, recrystallization is performed to obtain the 3- phenylpropylamine. According to the preparation method of the 3-phenylpropylamine disclosed by the embodiment of the invention, 3- phenylpropanol is used as a raw material, substitution reaction is performed to obtain the 1-chloro-3-phenylpropane, the 1-chloro-3-phenylpropane is reacted with the phthalimide salt to obtain the 2-(3-phenylpropyl)isoindoline-1,3-diketon, and then hydrazine hydrate hydrolysis is performed to obtain the 3-phenylpropylamine. The preparation method disclosed by the embodiment of the invention has the beneficial effects that the raw material required is cheap and easy to obtain, the reaction conditions are simple, the operation is simple and convenient, the toxicity and the pollution are small, the yield and the purity are high, and the method is suitable for industrial production.