1-methyl-3-(pentoxycarbonylmethyl)imidazolium octylsulfate | 911066-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-3-(pentoxycarbonylmethyl)imidazolium octylsulfate
• 英文别名: 3-methyl-1-(pentoxycarbonylmethyl)imidazolium octylsulfate；3-methyl-1-(pentoxycarbonylmethyl)imidazolium octyl sulfate；Octyl sulfate;pentyl 2-(3-methylimidazol-3-ium-1-yl)acetate
• CAS: 911066-18-7
• 化学式: C₈H₁₇O₄S*C₁₁H₁₉N₂O₂
• 分子量: 420.571
• InChiKey: YDARGFGOECQZLJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-methyl-3-(pentoxycarbonylmethyl)imidazolium bromide 、 sodium octyl sulphate 以 水 为溶剂， 反应 2.0h， 以96%的产率得到1-methyl-3-(pentoxycarbonylmethyl)imidazolium octylsulfate
  参考文献：
  名称：

  Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: A step towards ‘greener’ ionic liquids

  摘要：

  制备了一系列咪唑离子液体，并对7种细菌菌株进行了筛选。在酯侧链中引入醚基团与烷基酯衍生物相比显著降低了毒性。本文还提供了其中15种离子液体的生物降解数据，其中包括6个可归类为易生物降解的例子。

  DOI：

  10.1039/b812809j
• 作为试剂：
  描述：

  肉桂酸苄酯 在 palladium 10% on activated carbon 氢气 作用下， 以 1-methyl-3-(pentoxycarbonylmethyl)imidazolium octylsulfate 为溶剂， 反应 48.0h， 生成 Benzyl 3-phenylpropionate
  参考文献：
  名称：

  [EN] BIODEGRADABLE SOLVENTS FOR THE CHEMICAL INDUSTRY
  [FR] SOLVANTS BIODÉGRADABLES POUR L'INDUSTRIE CHIMIQUE

  摘要：

  这项发明涉及一种基于含有烷基-咪唑啉阳离子核心的离子液体溶剂，用于化学合成，这些离子液体相对于现有如1-丁基-3-甲基咪唑啉（bmmim）盐类的咪唑啉基离子液体，具有增强的生物降解性和降低的毒性。所描述的许多离子液体在生物降解性测试中，例如Sturm测试、封闭瓶测试（OECD 301D）或CO2顶空测试（ISO 14593）中，28天内生物降解率超过60%。本发明的离子液体包括一个在咪唑啉环的3位上带有-C=OX-侧链的烷基取代咪唑啉阳离子核心，其中X=O，NH，N或S，以及一个相关的反离子，其特征在于-C=OX侧链至少包含一个醚键。这些生物降解且无毒的离子液体可作为化学、制药、生物燃料和生物质工业的绿色溶剂。特别是，本发明的离子液体在氢化、周环和复分解反应中非常有用。

  公开号：

  WO2009024607A1

文献信息

• Further investigation of the biodegradability of imidazolium ionic liquids
  作者：Jitendra R. Harjani、Jeff Farrell、M. Teresa Garcia、Robert D. Singer、Peter J. Scammells

  DOI：10.1039/b900787c

  日期：——

  In continuation of our earlier investigations, this report presents a rationale behind the design of a series of imidazolium based ionic liquids and their biodegradation using the CO2 headspace test (ISO 14593 method, OECD 310). The effect on biodegradability of these salts through variation of the N-substituted side chains of imidazolium ions was examined further through incorporation of various functional groups and increased alkyl chain lengths. A series of anions containing moieties known to be biodegradable were also incorporated into a number of imidazolium based salts and examined in a similar fashion.

  本报告延续了我们之前的研究，介绍了一系列咪唑离子液体的设计原理，以及使用二氧化碳顶空试验（ISO 14593 方法，OECD 310）对其进行生物降解的情况。通过加入各种官能团和增加烷基链长度，进一步研究了咪唑离子 N 取代侧链的变化对这些盐类生物降解性的影响。一系列含有已知可生物降解分子的阴离子也被加入到一些咪唑盐中，并以类似的方式进行了研究。
• BIODEGRADABLE SOLVENTS FOR THE CHEMICAL INDUSTRY
  申请人：Gathergood Nick

  公开号：US20110201824A1

  公开（公告）日：2011-08-18

  This invention relates to ionic liquid (ILs) solvents for chemical synthesis based on an alkyl-imidazolium cation core containing ionic liquids which have enhanced biodegradability and reduced toxicity relative to existing imidazolium bases ILs such as 1-butyl-3-methylimidazolium (bmmim) salts. Many of the described ILs produce a score of over 60% biodegradability over 28 days in a biodegradability test such as the Sturm Test, the Closed Bottle Test (OECD 301D) or the CO 2 Headspace Test (ISO 14593). The ILs of the invention comprise an alkyl substituted imidazolium cationic core having a —C═OX— side chain in the 3-position of the imidazole ring, wherein X═O, NH, N or S and an associated counteranion characterized in that the —C═OX side chain comprises at least one ether linkage. The biodegradable and non-toxic IL may be used as green solvents for the chemical, pharmaceutical, biofuel and biomass industries. The ILs of the invention are particularly useful in hydrogenation, pericyclic and metathesis reactions.

  本发明涉及离子液体（ILs）溶剂用于基于含有增强生物降解性和降低毒性的烷基咪唑阳离子核心的化学合成的离子液体，相对于现有的咪唑基ILs，如1-丁基-3-甲基咪唑（bmmim）盐，许多所述的ILs在生物降解性测试中产生超过60％的生物降解性，如Sturm测试，闭瓶测试（OECD 301D）或CO2头空间测试（ISO 14593）。本发明的ILs包括一个烷基取代的咪唑阳离子核心，该核心在咪唑环的3位上具有一个—C═OX—侧链，其中X═O，NH，N或S，并且与之相关联的反离子的特征在于—C═OX侧链至少包含一个醚键。这种生物降解和无毒的IL可以用作化学，制药，生物燃料和生物质工业的绿色溶剂。本发明的ILs在氢化，周环和交换反应中特别有用。
• Ionic Liquid Solvents
  申请人：Gathergood Nicholas

  公开号：US20120071661A1

  公开（公告）日：2012-03-22

  A chiral ionic compound comprising an alkyl substituted imidazolium or pyridinium cationic core having an alkyl ester side chain (-alkyl-C(O)O—) directly linked to the core and an associated counter anion, characterized in that the —O— atom of the ester side chain is linked to an alpha, a beta or a gamma hydroxycarboxylic acid functionality via the alpha, beta or gamma hydroxy of the acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon, or characterized in that an —N═ atom of the alkyl substituted imidazolium or pyridinium cationic core is substituted with an alpha, a beta or a gamma hydroxy group of a alpha, a beta or a gamma hydroxycarboxylic acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon. The chiral ionic liquids (CILs) may be used as novel solvents, in particular for organic synthesis. The CILs have the potential to induce asymmetry into substrates or catalysts in a variety of organic transformations. A number of the compounds have low antimicrobial and low antifungal toxicities and are also biodegradable CILs.

  一种手性离子化合物，包括具有烷基取代的咪唑或吡啶阳离子核心，其具有直接连接到核心的烷基酯侧链（-alkyl-C（O）O-）和相关的对应阴离子。其特征在于酯侧链的-O-原子通过酸性官能团的α，β或γ羟基与α，β或γ羟基羟基羧酸官能团相连，并且羟基羧酸官能团具有至少一个不对称碳，或特征在于烷基取代的咪唑或吡啶阳离子核心的-N═原子被α，β或γ羟基羟基羧酸官能团的α，β或γ羟基取代，并且羟基羧酸官能团具有至少一个不对称碳。这些手性离子液体（CILs）可以作为新型溶剂，特别是用于有机合成。CILs有潜力在各种有机转化中引入对称性到底物或催化剂中。其中一些化合物具有低抗菌和低抗真菌毒性，并且也是可生物降解的CILs。
• Ionic liquid solvents
  申请人：Dublin City University

  公开号：EP2223915A1

  公开（公告）日：2010-09-01

  A chiral ionic compound comprising an alkyl substituted imidazolium cationic core having an alkyl ester side chain (-alkyl-C(O)O-) directly linked to the core and an associated counter anion, characterized in that the -O- atom of the ester side chain is linked to an alpha, a beta or a gamma hydroxycarboxylic acid functionality via the alpha, beta or gamma hydroxy of the acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon.The chiral ionic liquids (CILs)may be used as novel solvents for organic synthesis. The CILs have the potential to induce asymmetry into substrates or catalysts in a variety of organic transformations. A number of the compounds are biodegradable CILs.

  一种手性离子化合物，包括一个烷基取代的咪唑阳离子核心，该核心具有一个直接连接到核心的烷基酯侧链（-烷基-C(O)O-）和一个相关的反离子、 手性离子液体（CIL）可用作有机合成的新型溶剂。手性离子液体（CILs）可用作有机合成的新型溶剂。CILs 具有在各种有机转化过程中诱导底物或催化剂产生不对称的潜力。其中一些化合物是可生物降解的 CIL。
• IONIC LIQUID MEDIATED SOL-GEL SORBENTS
  申请人：Abdul Malik

  公开号：US20120128551A1

  公开（公告）日：2012-05-24

  Ionic liquid (IL)-mediated sol-gel hybrid organic-inorganic materials present enormous potential for effective use in analytical microextraction. One obstacle to materializing this prospect arises from high viscosity of ILs significantly slowing down sol-gel reactions. A method was developed which provides phosphonium-based, pyridinium-based, and imidazolium-based IL-mediated advanced sol-gel organic-inorganic hybrid materials for capillary microextraction. Scanning electron microscopy results demonstrate that ILs can serve as porogenic agents in sol-gel reactions. IL-mediated sol-gel coatings prepared with silanol-terminated polymers provided up to 28 times higher extractions compared to analogous sol-gel coatings prepared without any IL in the sol solution. This study shows that IL-generated porous morphology alone is not enough to provide effective extraction media: careful choice of the organic polymer and the precursor with close sol-gel reactivity must be made to ensure effective chemical bonding of the organic polymer to the created sol-gel material to be able to provide the desired sorbent characteristics.