112-47-0Relevant articles and documents
The synthesis of phosphates of long-chain ω-hydroxyalkyl esters of 11-deoxyprostaglandin E1
Sokolov,Turovskii,Lukevits
, p. 62 - 64 (2002)
Di(p-methylbenzyl) phosphates of ω-hydroxyalkyl esters of 11-deoxyprostaglandin E1 were synthesized from disubstituted 1,10-decane and 1,22-docosane derivatives for studying the permeability of bilayer membranes.
Borane evolution and its application to organic synthesis using the phase-vanishing method
Soga, Nene,Yoshiki, Tomo,Sato, Aoi,Kawamoto, Takuji,Ryu, Ilhyong,Matsubara, Hiroshi
, (2021)
Although borane is a useful reagent, it is difficult to handle. In this study, borane was generated in situ from NaBH4 or nBu4NBH4 with several oxidants using a phase-vanishing (PV) method. The borane generated was directly reacted with alkenes, affording the desired alcohols in good yields after oxidation with H2O2 under basic conditions. The selective reduction of carboxylic acids with the evolved borane was examined. The organoboranes generated by the PV method successfully underwent Suzuki–Miyaura coupling. Using this PV system, reactions with borane can be carried out easily and safely in a common test tube.
From intermolecular interactions to texture in polycrystalline surfaces of 1,ω-alkanediols (ω = 10–13)
Luis-Raya, Gilgamesh,Ramírez-Cardona, Màrius,Luna-Bárcenas, Gabriel,Hernández-Landaverde, Martín A.,Jiménez-Nieto, Adair,García-Rivas, Jose Luis,Espa A-Sánchez, Beatriz Liliana,Sanchez, Isaac C.
, (2017)
Differences on herringbone molecular arrangement in two forms of long-chain 1,?-alkanediols (CnH2n+2O2 with n = 10, 11, 12, 13) are explained from the analysis of O-H···O hydrogen-bond sequences in infinite chains and the role of a C-H···O intramolecular hydrogen-bond in stabilization of a gauche defect, as well as the inter-grooving effectiveness on molecular packing. GIXD (Glancing Incidence X-ray Diffraction) experiments were conducted on polycrystalline monophasic samples. Diffracted intensities were treated with the multi-axial March-Dollase method to correlate energetic and geometrical features of molecular interactions with the crystalline morphology and textural pattern of samples. The monoclinic (P21/c, Z = 2) crystals of the even-numbered members (n = 10, 12; DEDOL and DODOL, respectively) are diametrical prisms with combined form {104}/{-104}/{001} and present a two-fold platelet-like preferred orientation, whereas orthorhombic (P212121, Z = 4) odd-numbered members (n = 11, 13; UNDOL and TRDOL, respectively) present a dominant needle-like orientation on direction [101] (fiber texture). We show that crystalline structures of medium complexity and their microstructures can be determined from rapid GIXD experiments from standard radiation, combined with molecular replacement procedure using crystal structures of compounds with higher chain lengths as reference data.
The head-to-head reductive coupling of homoallylic alcohols promoted by titanium(II)-olefin complexes
Isakov, Vladimir E.,Kulinkovich, Oleg G.
, p. 967 - 970 (2003)
Reaction of homoallylic alcohols 1a-e with i-PrMgBr in the presence of Ti(i-PrO)4 leads to the unbranched saturated diols 2a-e as the main products in moderate to good yields. The head-to-head regioselectivity in reductive coupling of 4-penten-
Pheromones of insects and their analogs. LII. Sythesis of dodec-9-en-1-yl and tetradec-11-en-1-yl acetates from the products of the partial ozonolysis of cycloocta-1z,5z-diene and cyclodeca-1e,5z-diene
Odinokov,Botsman,Gladysheva
, p. 381 - 383 (1996)
A new approach to the synthesis of octane-1,8-and decane-1,10-diols based on the partial ozonolysis of cyclic oligomers has been developed.
ELECTROCHEMICAL REDUCTIONS IN LIQUID AMMONIA: ELECTROLYTIC BIRCH REACTIONS AND CHEMICAL BOND FISSIONS
Chaussard, J.,Combellas, C.,Thiebault, A.
, p. 1173 - 1174 (1987)
A procedure of electrochemical reduction in liquid ammonia using a single-compartment cell equiped with a soluble anode is described and illustrated in the case of aromatic compounds and esters.
Hydroboration Reaction and Mechanism of Carboxylic Acids using NaNH2(BH3)2, a Hydroboration Reagent with Reducing Capability between NaBH4and LiAlH4
Wang, Jin,Ju, Ming-Yue,Wang, Xinghua,Ma, Yan-Na,Wei, Donghui,Chen, Xuenian
, p. 5305 - 5316 (2021/04/12)
Hydroboration reactions of carboxylic acids using sodium aminodiboranate (NaNH2[BH3]2, NaADBH) to form primary alcohols were systematically investigated, and the reduction mechanism was elucidated experimentally and computationally. The transfer of hydride ions from B atoms to C atoms, the key step in the mechanism, was theoretically illustrated and supported by experimental results. The intermediates of NH2B2H5, PhCH= CHCOOBH2NH2BH3-, PhCH= CHCH2OBO, and the byproducts of BH4-, NH2BH2, and NH2BH3- were identified and characterized by 11B and 1H NMR. The reducing capacity of NaADBH was found between that of NaBH4 and LiAlH4. We have thus found that NaADBH is a promising reducing agent for hydroboration because of its stability and easy handling. These reactions exhibit excellent yields and good selectivity, therefore providing alternative synthetic approaches for the conversion of carboxylic acids to primary alcohols with a wide range of functional group tolerance.
Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)
Matsuoka, Keitaro,Komami, Narumi,Kojima, Masahiro,Mita, Tsuyoshi,Suzuki, Kimichi,Maeda, Satoshi,Yoshino, Tatsuhiko,Matsunaga, Shigeki
, p. 103 - 108 (2021/01/13)
Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.
