10160-24-4Relevant articles and documents
Functional group transformations of diols, cyclic ethers, and lactones using aqueous hydrobromic acid and phase transfer catalyst under microwave irradiation
Kad, Goverdhan L.,Kaur, Irvinder,Bhandari, Monica,Singh, Jasvinder,Kaur, Jasamrit
, p. 339 - 340 (2003)
Synthesis of bromoalkanols has been achieved from diols, ethers, and lactones using aq HBr (48%) and tetrabutylammonium iodide/bromide as phase transfer catalyst under microwave irradiation. This environmentally benign route provides enhanced yields of products and does away with the use of benzene as compared to existing conventional methods.
New synthesis of nematocidal natural products dithiocynates thiocyanatin A and 1,8,16-trihydroxyhexadecane
Singh, Ashima,Sharma,Singh, Jasvinder
, p. 1029 - 1034 (2009)
A new and short synthesis of nematocidal natural products, thiocyanatin A and 1,8,16-trihydroxyhexadecane, from readily available starting compounds 1,7-heptanediol and 1,9-nonanediol in six steps is described.
Rhodium-catalyzed reduction of esters to alcohols using diphenylsilane
Ohta, Tetsuo,Kamiya, Masahiro,Kusui, Keisuke,Michibata, Tsugumi,Nobutomo, Mami,Furukawa, Isao
, p. 6963 - 6966 (1999)
Carboxylic esters were reduced to alcohols by diphenylsilane catalyzed by a Rh complex at room temperature. For example, ethyl decanoate and ethyl phenylacetate were converted to decanol and 2-phenylethanol by [RhCl(cod)]2 / 4PPh3 for 72 hours in 98 and 92% yields, respectively. Wilkinson's catalyst is also usable, and the reduction of ethyl decanoate finished in 6 hours at room temperature. The bromo-substituent on ethyl 7-bromoheptanoate remained intact through this reduction.
New method for synthesis of methacrylate-type polymerizable ionic liquids
Pohako-Esko, Kaija,Taaber, Triinu,Saal, Kristjan,Lohmus, Ruenno,Kink, Ilmar,Maeeorg, Uno
, p. 2846 - 2852 (2013)
A new method for the synthesis of polymerizable ionic liquids bearing a methacrylate moiety was developed with the aim to avoid premature polymerization of synthesized compounds. Spacer length between the imidazolium cation and the polymerizable functional group varied from 2 to 10 carbon atoms. Different 1-(n-hydroxyalkyl)-3-methylimidazolium bromides and 1-[n-(methacryloyloxy)- alkyl]-3-methylimidazolium bromides were obtained with very good yields (more than 90%).
Simple but precise engineering of functional nanocapsules through nanoprecipitation
Yan, Xibo,Delgado, Marco,Fu, Amy,Alcouffe, Pierre,Gouin, Sebastien G.,Fleury, Etienne,Katz, Joseph L.,Ganachaud, Francois,Bernard, Julien
, p. 6910 - 6913 (2014)
A general, rapid, and undemanding method to generate at will functional oil-filled nanocapsules through nanoprecipitation is reported. On the basis of polymer and hexadecane/water/acetone phase diagrams, the composition can be set so that polymer chains p
Reduction of carboxylic acid derivatives using diphenylsilane in the presence of a Rh-PPh3 complex
Ohta, Tetsuo,Kamiya, Masahiro,Nobutomo, Mami,Kusui, Keisuke,Furukawa, Isao
, p. 1856 - 1861 (2005)
Reductions of carboxylic acid derivatives by silanes in the presence of rhodium complexes were studied. Carboxylic esters were reduced to alcohols by diphenylsilane catalyzed by [RhCl(cod)]2/4PPh3 or [RhCl(PPh3)3] at room temperature in up to 99% yields. For example, ethyl decanoate and ethyl phenylacetate were converted to decanol and 2-phenylethanol in 98 and 92% yields, respectively. Carboxylic acids were also reduced by this reducing system to the corresponding alcohols in high yields. Furthermore, N-monosubstituted amides were reduced to secondary amines in moderate to good yields. For sterically hindered amides, the yields were moderate, and imines were produced in competitive yields.
Stereoselective synthesis of the Paulownia bagworm sex pheromone
Sun, Zhi-Feng,Zhou, Lu-Nan,Zhang, Tao,Du, Zhen-Ting
, p. 558 - 562 (2017)
According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.
Total Synthesis of the Antitumor Depsipeptide FE399 and Its S-Benzyl Derivative: A Macrolactamization Approach
Tonoi, Takayuki,Ikeda, Miyuki,Sato, Teruyuki,Inohana, Takehiko,Kawahara, Ryo,Murata, Takatsugu,Shiina, Isamu
, p. 5119 - 5125 (2020)
An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.
Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella.
Mozuraitis, Raimondas,Buda, Vincas,Liblikas, Ilme,Unelius, Carl Rikard,Borg-Karlson, Anna-Karin
, p. 1191 - 1208 (2002)
We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E, 10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.
A mild and versatile method for the tetrahydropyranylation of alcohols and their detetrahydropyranylation
Yadav,Srinivas, Dale,Reddy, Gondi Sudershan
, p. 1399 - 1404 (1998)
An efficient and mild method for tetrahydropyranylation of alcohols and their detetrahydropranylation using NH4Cl is described. This protocol provides a useful alternative tetrahydropyranylation of alcohols and their deprotection at different pH.
