19448-36-3Relevant articles and documents
Photoinduced Molecular Transformations. Part 154. On the Mechanism of the Formation of the 5-Iodopentyl Formate in the Photolysis of Cyclopentanol Hypoiodite in Solution in the Presence of Mercury(II) Oxide-Iodine.
Suginome, Hiroshi,Senboku, Hisanori
, p. 13101 - 13112 (1994)
(18)O-labelling experiments established that the formation of 5-iodopentyl formate in the photolysis of cyclopentanol hypoiodite in the presence of excess mercury(II) oxide-iodine in benzene involves the following pathway: a) a β-scission of a cyclopentyloxy radical to rearrange to a primary 5-oxopentyl radical, which generates the corresponding carbocation by a metal ionassisted one-electron oxidation; b) an intramolecular addition of the 5-oxopentyl cation to the formyl oxygen to generate a tetrahydropyranyl cation; c) a combination of the tetrahydropyranyl cation with diiodine oxide (I2O) to form a lactol hypoiodite; d) generation of a carbon-centred radical by a selective β-scission of a carbon-carbon bond of an alkoxyl radical generated from the lactol hypoiodite; e) abstraction of an iodine by the carbon-centred radical from an iodine molecule to form the 5-iodopentyl formate. 5-Iodopentyl formate is also produced by prolonged irradiation of a solution of 5-iodopentanal in the presence of mercury(II) oxide and iodine in benzene with Pyrex-filtered light.The formate in this case should be formed through the generation of the 5-oxopentyl cation (mentioned above) by mercury-assisted ionization of its carbon-iodine bond, followed by the same pathway as that mentioned above.
Synthesis of dl-9(O)-methano-Δ6-prostaglandin I1
Iseki,Mase,Okazaki,et al.
, p. 4448 - 4455 (1983)
Biologically interesting 9(O)-methano-Δ6-prostaglandin I1 (9(O)-methano-Δ6-PGI1), a chemically stable analog of prostacyclin (PGI2), was efficiently synthesized from 1,3-cyclooctadiene with high stereo- and regiochemical control. In all three biological test systems examined, 9(O)-methano-Δ6-PGI1 was found to be considerably less active than prostaglandin E1 (PGE1).
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Efficient Synthesis of ω-[18F]Fluoroaliphatic Carboxylic Esters and Acids for Positron Emission Tomography
Belousov, Mikhail V.,Larkina, Mariia S.,Ozerskaya, Anastasia V.,Podrezova, Ekaterina V.,Tolmachev, Vladimir,Yusubov, Mekhman S.,Zhdankin, Viktor V.
, p. 6375 - 6381 (2020/10/20)
[18F]Fluoroaliphatic carboxylic acids are important PET tracers that have demonstrated a considerable potential to address the fatty acid oxidation-dependent processes in clinical patients. Herein, we report an efficient radiosynthetic approach to ω-[18F]fluoroaliphatic carboxylic esters and acids by nucleophilic radiofluorination of the readily available iodocarboxylic esters. Methyl 6-[18F]fluorohexanoate was further applied as a starting material for the preparation of the succinimide ester (NHS ester)-containing bifunctional radiofluorinated prosthetic group in two simple steps, 10 min each. The synthesized NHS ester of 6-[18F]fluorohexanoic acid can serve as an important reagent for a quick and efficient conjugation with peptides or proteins via amino groups of lysines.
Expedient synthesis of long-chain ω-substituted fatty acids and esters from cyclic ketones using iodine and hydrogen peroxide
Podrezova, Ekaterina V.,Larkina, Maria S.,Belousov, Mikhail V.,Kirschning, Andreas,Zhdankin, Viktor V.,Yusubov, Mekhman S.
, p. 4081 - 4088 (2018/10/15)
A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.
CHELATING COMPOUNDS AND IMMOBILIZED TETHERED CHELATORS
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, (2009/10/30)
Novel di- and tripodal compounds useful as chelators, intermediates for their production and a method for treating an aqueous solution to remove trivalent metal ions are presented.
Progressive-convergent elucidation of stereochemistry in complex polyols. The absolute configuration of (-)-sagittamide A
Lievens, Sarah C.,Molinski, Tadeusz F.
, p. 11764 - 11765 (2007/10/03)
The absolute stereostructure of sagittamide A (1), a O-hexacetyl long-chain hexahydroxy-α,ω-dicarboxylic acid, was assigned using a progressive-convergent approach that integrates three powerful regimens for stereochemical analysis of acyclic natural prod
Facile synthesis of (+)-biotin via Fukuyama coupling reaction
Shimizu, Toshiaki,Seki, Masahiko
, p. 5099 - 5101 (2007/10/03)
Treatment of a thiolactone 2 with a zinc reagent 3 in the presence of PdCl2(PPh3)2 (10 mol%) allowed installation of a C-2 side chain of (+)- biotin in a highly efficient manner, which enabled synthesis of (+)biotin in three steps from 2. (C) 2000 Elsevier Science Ltd.
CONTROLLING STEREOCHEMISTRY IN RADICAL ADDITION AND CYCLIZATION REACTIONS WITH OPPOLZER'S CAMPHOR SULTAM
Curran, Dennis P.,Shen, Wang,Zhang, Jiancun,Gieb, Steven J.,Lin, Chien-Hsing
, p. 1773 - 1788 (2007/10/02)
Acrylate derivatives of Oppolzer's camphor sultam exhibit good to excellent levels of stereoselectivity in typical radical allylations and alkene and alkyne cyclizations.
LACTONIZATION REACTIONS OF (Ω-CARBOXYALKYL)SULFONIUM SALTS
Nakamura, Takako,Matsuyama, Haruo,Takahashi, Masaya,Kamigata, Nobumasa
, p. 59 - 66 (2007/10/02)
The intramolecular cyclizations of sulfonium salts having an ω-carboxyalkyl group were investigated for the synthesis of five- to nine-membered lactones, and five- to seven-membered lactones were obtained in good yields from S-(ω-carboxyalkyl)thiolanium salts.The scope and limitations of the synthetic utility of the reaction are indicated by this study. Key words: Lactonization reactions; (ω-carboxyalkyl)diphenylsulfonium salts; S-(ω-carboxyalkyl)thiolanium salts; medium-sized lactones; large-sized lactones; sulfur-containing lactones.
