- Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation
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Diimine (HN═NH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.
- Chen, Guoliang,He, Xiaoyan,Huang, Gang,Lu, Xiuhong,Wang, Jincheng,Yang, Zhenjiao,Zhang, Yongsheng,Zhang, Zeng
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p. 17696 - 17709
(2021/12/09)
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- Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
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Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
- Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
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supporting information
p. 2544 - 2550
(2019/11/13)
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- Novel Process for the Synthesis of Docosanol
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The present invention relates to a novel process for the preparation of Docosanol (I). More particularly, the invention relates to a novel process for the preparation of Docosanol (I) in a substantially pure form with a purity level of greater than 99.5%. The invention also relates to novel crystalline forms of Docosanol (I) and process for preparation thereof.
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- A PROCESS FOR THE PREPARATION OF DOCOSANOL
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The present invention provides a process for the preparation of Docosanol (I). The process comprises reducing cis-13-Docosenoic acid (V) to obtain Docosanoic acid (III), which is further reduced to obtain Docosanol (I).
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Page/Page column 8; 9
(2019/01/05)
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- Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent
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In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.
- Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro
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p. 604 - 608
(2014/01/23)
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- METHOD FOR THE PRODUCTION OF PRIMARY LONG-CHAIN ALCOHOLS
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The invention relates to a method for the production of linear long-chain alcohols with 20 to 40 carbon atoms by means of a growth reaction with ethylene on aluminium compounds.
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Page/Page column 11-12
(2010/02/15)
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- A Convenient Method for Protection and Deprotection of Alcohols and Phenols as Alkylsilyl Ethers Catalyzed by Iodine under Microwave Irradiation
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Irradiation of alcohols or phenols with tert-butyldimethylsilyl chloride (TBDMSCl) or trimethylsilyl chloride (TMSCl) in presence of catalytic amount (20 mol%) of iodine in a microwave oven for 2 min gives the corresponding silyl ethers in excellent yield. Iodine in methanol deprotects the silyl ether into its parent alcohol or phenol under similar reaction conditions.
- Saxena, Ira,Deka, Nabajyoti,Sarma, Jadab C.,Tsuboi, Sadao
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p. 4185 - 4191
(2007/10/03)
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- A facile synthesis of long chain acyclic alkanols via Kolbe coupling: 1-Docosanol and 1-triacontanol
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A convenient synthesis of long chain acyclic alkanols viz., 1-docosanol and 1-triacontanol has been devised via Kolbe radical coupling of mono-methyl azelate 2, which has been synthesized from azelaic acid 1. The dimer viz. dimethyl thapsate 3, on Ba(OH)2 hydrolysis affords mono-methyl thapsate 4, which upon mixed Kolbe coupling with appropriate alkanoic acid [CH3(CH)2)nCOOH, n = 6 for 1-docosanol and n = 14 for 1-tri-acontanol] gives the cross coupled products methyl docosanoate 7 and methyl triacontanoate 8 along with the radical dimers dimethyl triacontanedioate 4′ and tetradecane 5′/triacontane 6′ as byproducts. Compounds 7 and 8 on LAH reduction in dry THF yield 1-docosanol 9 and 1- triacontanol 10, respectively in high yields. The mixed anodic coupling has been studied by varying parameters viz. degree of neutralization and molar ratio of compounds 4 and C8/C16 alkanoic acid, current density, anode material etc.
- Yadav, Ashok K.,Singh, Arpita
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p. 1724 - 1726
(2007/10/03)
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- Microwave assisted catalytic protection and deprotection of alcohols with 3,4-dihydro-2h-pyran
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Protection of alcohols as their 2-tetrahydropyranyl ethers and their subsequent hydrolysis can be easily achieved through a microwave irradiated reaction catalysed by iodine.
- Deka,Sarma
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p. 4435 - 4441
(2007/10/03)
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- Copper(II) chloride dihydrate: A catalytic agent for the deprotection of tetrahydropyranyl ethers (THP ethers) and 1-ethoxyethyl ethers (EE ethers)
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Tetrahydropyranyl ethers (THP groups) and 1-ethoxyethyl ethers (EE groups) are removed upon refluxing in 95% EtOH or Me2CO-H2O (95:5) in the presence of a catalytic amount of copper(II) chloride dihydrate (2-5 mol%).
- Wang, Jianbo,Zhang, Chao,Qu, Zhaohui,Hou, Yihua,Chen, Bei,Wu, Peng
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p. 294 - 295
(2007/10/03)
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- Magnesium-tin(II) chloride dihydrate: A new system for chemoselective reduction of aldehydes into alcohols in the presence of ketones, ketalization of ketones and dehalogenation of benzyl halides
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Magnesium-tin (II) chloride dihydrate in THF efficiently reduced aldehydes into their corresponding alcohols chemoselectively in the presence of ketones, formed ketals with ketones and glycol and dehalogenated benzyl halides.
- Bordoloi, Manobjyoti,Sharma, Ram P.,Chakraborty, Vaishali
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p. 2501 - 2506
(2007/10/03)
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- Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
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The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.
- Alonso, Emma,Ramon, Diego J.,Yus, Miguel
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p. 14355 - 14368
(2007/10/03)
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- Synthesis of 1-docosanol
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The synthesis of 1-docosanol 1, starting from palmitaldehyde 2 by dithiane 3 and Wittig approach, is described.
- Deshmukh,Veeresh
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p. 1239 - 1241
(2007/10/03)
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- Higher alkanol compositions and the use thereof in treatment of prostate disorders
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This invention is concerned with a therapeutic composition intended in particular for the treatment of secretory disorders of the prostate gland, containing a pharmaceutically active quantity of at least one higher alkanol with 16 or more carbon atoms or one of its esters in association with a physiologically acceptable vehicle.
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