5070-13-3Relevant articles and documents
Photo-on-Demand Base-Catalyzed Phosgenation Reactions with Chloroform: Synthesis of Arylcarbonate and Halocarbonate Esters
Dai, Namin,Eda, Kazuo,Harada, Hidefumi,Hashimoto, Yuka,Hosokawa, Sasuga,Kakiuchi, Toshifumi,Liang, Fengying,Okazoe, Takashi,Suzuki, Yuto,Tana, Gegen,Tsuda, Akihiko
, p. 9811 - 9819 (2021/07/20)
Carbonate esters are utilized as solvents and reagents for C1 building blocks in organic synthesis. This study reports a novel photo-on-demand in situ synthesis of carbonate esters with CHCl3 solutions containing a mixture of an aromatic or haloalkyl alcohol having relatively high acidity, and an organic base. We found that the acid-base interaction of the alcohol and base in the CHCl3 solution plays a key role in enabling the photochemical reaction. This reaction allows practical syntheses of diphenyl carbonate derivatives, haloalkyl carbonates, and polycarbonates, which are important chemicals and materials in industry.
CARBONATE DERIVATIVE PRODUCTION METHOD
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Paragraph 0135-0136; 0143-0144, (2020/04/09)
The objective of the present invention is to provide a method for producing a carbonate derivative in a safe and efficient manner. The method for producing a carbonate derivative according to the present invention is characterized in comprising irradiating light on a composition containing a C1-4 halogenated hydrocarbon having one or more kinds of halogen atoms selected from the group consisting of a chlorine atom, a bromine atom and an iodine atom, a nucleophilic functional group-containing compound and the specific base in the presence of oxygen.
Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6 H)-carboxylates: A practical alternative to chloroformates for the synthesis of symmetric and asymmetric carbonates
Moon, Hyun Kyung,Sung, Gi Hyeon,Yoon, Yong-Jin,Yoon, Hyo Jae
supporting information, p. 1577 - 1581 (2016/06/14)
Symmetric and asymmetric carbonates were synthesized by using alkyl or aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates. Five aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were converted into the corresponding diaryl carbonates in good to excellent yields by treatment with potassium carbonate in refluxing THF. When the 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were treated with aliphatic or aromatic alcohols in the presence of potassium tert-butoxide in toluene at room temperature, they gave the corresponding symmetric or asymmetric carbonates in moderate to excellent yields. Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates are therefore efficient, stable, and ecofriendly alternatives to chloroformates.
Synthesis of organic carbonates with alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl3under ambient condition
Sung, Gi Hyeon,Bo, Ram Kim,Ryu, Ki Eun,Kim, Jeum-Jong,Yoon, Yong-Jin
, p. 2758 - 2764 (2015/04/22)
We demonstrated the synthesis of organic carbonates using alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and alcohol in the presence of aluminum chloride. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates were reacted with alcohol in the presence of AlCl3 in toluene at room temperature to afford the corresponding unsymmetric and symmetric organic carbonates in good to excellent yields. These are efficient and convenient processes. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates are solid, stable and non-toxic CO2/CO2R(Ar) source. It is noteworthy that the reaction is carry out under an ambient and acidic conditions, the easy-to prepare and readily available starting materials and the quantitative isolation of reusable 4,5-dichloropyridazin-3(2H)-one.
Study of the kulinkovich synthesis of 1-methylcyclopropanol and its conversion into 1-methylcyclopropyl 4-nitrophenyl carbonate
Wright, Stephen W.,Darout, Etzer,Stevens, Benjamin D.
, p. 2481 - 2484 (2013/09/23)
A detailed investigation of the preparation of 1-methylcyclopropanol via the Kulinkovich reaction is presented. Reaction and workup parameters were optimized to provide a reproducible procedure for the synthesis of multigram quantities of 1-methylcyclopropanol. Key improvements were the use of titanium tetra(2-ethyl)hexyloxide as catalyst, reduction in the volume of reaction solvent, addition of the methyl acetate starting material in portions, and azeotropic distillation to remove by-products. The preparation of the 4-nitrophenyl carbonate ester was likewise studied and optimized. Georg Thieme Verlag Stuttgart New York.
Photochemical molecular storage of Cl2, HCl, and COCl 2: Synthesis of organochlorine compounds, salts, ureas, and polycarbonate with photodecomposed chloroform
Kuwahara, Yuki,Zhang, Ailing,Soma, Haruka,Tsuda, Akihiko
supporting information; experimental part, p. 3376 - 3379 (2012/08/08)
Chloroform is available as not only an organic solvent but also photochemical molecular storage for synthetically important chemicals such as Cl2, HCl, and COCl2. We have succeeded in synthesizing organochlorine compounds, hydrochloric salt of amines, ureas, organic carbonates, and polycarbonate in practical high yields with photodecomposed chloroform.
Protein micro- and nanopatterning using aminosilanes with protein-resistant photolabile protecting groups
Alang Ahmad, Shahrul A.,Wong, Lu Shin,Ul-Haq, Ehtsham,Hobbs, Jamie K.,Leggett, Graham J.,Micklefield, Jason
, p. 2749 - 2759 (2011/04/23)
An approach to the integration of nanolithography with synthetic chemical methodology is described, in which near-field optical techniques are used to selectively deprotect films formed by the adsorption of aminosilanes protected by modified 2-nitrophenylethoxycarbonyl (NPEOC) groups. The NPEOC groups are functionalized at the m- or p-position with either a tetraethyleneglycol or a heptaethylene glycol adduct. We describe the synthesis of these bioresistant aminosilanes and the characterization of the resulting photoreactive films. Photodeprotection by exposure to UV light (λ = 325 nm) yielded the amine with high efficiency, at a similar rate for all four adsorbates, and was complete after an exposure of 2.24 J cm-2. Following photodeprotection, derivatization by trifluoroacetic anhydride was carried out with high efficiency. Micropatterned samples, formed using a mask, were derivatized with aldehyde-functionalized polymer nanoparticles and, following derivatization with biotin, were used to form patterns of avidin-coated polymer particles. Fluorescence microscopy and atomic force microscopy data demonstrated that the intact protecting groups conferred excellent resistance to nonspecific adsorption. Nanometer-scale patterns were created using scanning near-field photolithography and were derivatized with biotin. Subsequent conjugation with avidin-functionalized polymer nanoparticles yielded clear fluorescence images that indicated dense attachment to the nanostructures and excellent protein resistance on the surrounding surface. These simple photocleavable protecting group strategies, combined with the use of near-field exposure, offer excellent prospects for the control of surface reactivity at nanometer resolution in biological systems and offer promise for integrating the top-down and bottom-up molecular fabrication paradigms.
Structural features of phenoxycarbonylimino neonicotinoids acting at the insect nicotinic receptor
Ohno, Ikuya,Tomizawa, Motohiro,Miyazu, Nozomi,Kushibiki, Gohito,Noda, Kumiko,Hasebe, Yasunori,Durkin, Kathleen A.,Miyake, Taiji,Kagabu, Shinzo
scheme or table, p. 5933 - 5935 (2010/11/18)
Substituted-phenoxycarbonylimino neonicotinoid ligands with an electron-donating group showed significantly higher affinity to the insect nicotinic receptor relative to that of the analogue with an electron-withdrawing substituent, thereby establishing in silico binding site interaction model featuring that the phenoxy ring of neonicotinoids and the receptor loop D tryptophan indole plane form a face-to-edge aromatic interaction.
Stereoselective synthesis of α-Keto-deoxy-D-glycero-D- galactononulosonic acid glycosides by means of the 4,5-O-carbonate protecting group
Crich, David,Navuluri, Chandrasekhar
supporting information; experimental part, p. 3049 - 3052 (2010/07/05)
(Figure Presented) Unrivaled: A 1-adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5-O-carbonate protecting group, is a highly efficient and a-selective KDN donor when activated using N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylates conducted with this protecting group do not suffer from competing glycal formation.
Telluroxides exhibit hydrolysis capacity
Dong, Zeyuan,Li, Xiangqiu,Liang, Kai,Mao, Shizhong,Huang, Xin,Yang, Bing,Xu, Jiayun,Liu, Junqiu,Luo, Guimin,Shen, Jiacong
, p. 606 - 609 (2007/10/03)
It has long been known that tellurium compounds are rather toxic to living organisms, and tellurium has not been found in natural biomacromolecules to date. The principles of telluride toxicity in biological processes are still controversial partly because of the lack of information on the biochemical features of tellurium. In this contribution, we report our finding for the first time that telluroxides exhibit hydrolysis capacity. For instance, 6,6′-telluroxy-bis(6-deoxy-β-cyclodextrin) acts as a hydrolase mimic and shows a significant rate acceleration of 106 000 for the hydrolysis of 4,4′-dinitrodiphenyl carbonate.
