1-(2-hydroxyethyl)-1-methylpiperidinium-bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2-hydroxyethyl)-1-methylpiperidinium-bromide
• 英文别名: N-(2-hydroxyethyl)-N-methylpiperidinium bromide；N-hydroxyethyl-N-methylpiperidine bromide；2-(1-Methylpiperidin-1-ium-1-yl)ethanol;bromide
• 化学式: Br*C₈H₁₈NO
• 分子量: 224.141
• InChiKey: LDHFANIBASKXBJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(trifluoromethane)sulfonimide lithium 、 1-(2-hydroxyethyl)-1-methylpiperidinium-bromide 以 水 为溶剂， 反应 1.0h， 以68%的产率得到N-(2-hydroxyethyl)-N-methylpiperidinium bis[(trifluoromethyl)sulfonyl]imide
  参考文献：
  名称：

  NMR氘核四极子耦合常数与盐桥和分子系统的比较，表征了离子液体中类似电荷的氢键。

  摘要：

  我们介绍了在结晶或玻璃态下表征两种氢键的羟基官能化离子液体（IL）的氘代四极偶合常数（DQCC），其特征在于两种类型的氢键：阳离子和阴离子之间的常规库仑增强氢键（ca），以及不寻常的氢阳离子与阳离子（cc）之间的键，尽管存在库仑排斥力，但它们仍然存在。我们通过固态NMR光谱法测量了这些敏感的氢键探针。将（ca）离子对和（cc）H键的DQCC与超分子络合物中的盐桥和分子液体中的DQCC进行比较。在低温下，（cc）物种成功地与（ca）离子对竞争，并主导了簇群。从分子动力学（MD）模拟获得的平衡常数表明van' 在不同氢键键合的物种之间具有小的过渡焓的Hoff行为。我们表明，阳离子簇的形成阻止了这些IL的结晶。随着冷却，（cc）氢键持续存在，导致过冷和玻璃形成。

  DOI：

  10.1002/anie.201912476
• 作为产物：
  描述：

  N-甲基哌啶 、 2-溴乙醇 以 乙醇 为溶剂， 以89%的产率得到1-(2-hydroxyethyl)-1-methylpiperidinium-bromide
  参考文献：
  名称：

  NMR氘核四极子耦合常数与盐桥和分子系统的比较，表征了离子液体中类似电荷的氢键。

  摘要：

  我们介绍了在结晶或玻璃态下表征两种氢键的羟基官能化离子液体（IL）的氘代四极偶合常数（DQCC），其特征在于两种类型的氢键：阳离子和阴离子之间的常规库仑增强氢键（ca），以及不寻常的氢阳离子与阳离子（cc）之间的键，尽管存在库仑排斥力，但它们仍然存在。我们通过固态NMR光谱法测量了这些敏感的氢键探针。将（ca）离子对和（cc）H键的DQCC与超分子络合物中的盐桥和分子液体中的DQCC进行比较。在低温下，（cc）物种成功地与（ca）离子对竞争，并主导了簇群。从分子动力学（MD）模拟获得的平衡常数表明van' 在不同氢键键合的物种之间具有小的过渡焓的Hoff行为。我们表明，阳离子簇的形成阻止了这些IL的结晶。随着冷却，（cc）氢键持续存在，导致过冷和玻璃形成。

  DOI：

  10.1002/anie.201912476

文献信息

• PROCESS FOR PRODUCING ETHYLENE GLYCOL CATALYZED BY IONIC LIQUID
  申请人：Zhang Suojiang

  公开号：US20130072727A1

  公开（公告）日：2013-03-21

  Disclosed is a process for producing ethylene glycol catalyzed by an ionic liquid, characterized in that the process includes the following three steps: (a) a carbonylation step of ethylene oxide and CO 2 catalyzed by an ionic liquid composite catalyst comprising a hydroxyl functionalized ionic liquid and an alkali metal salt under an aqueous condition to produce ethylene carbonate and ethylene glycol; (b) a hydrolysis step of reacting the reaction solution containing ethylene carbonate and the ionic liquid composite catalyst obtained in step (a) with water to produce ethylene glycol; (c) a purification step of dehydrating and refining ethylene glycol from the aqueous solution containing ethylene glycol and the catalyst produced in step (b). The present process has the following advantages: the catalyst has high activity, high suitability, and good stability, the reaction condition is wild, the conversion of ethylene oxide is high, the selectivity of ethylene glycol is high, and the process is simple.

  揭示了一种由离子液体催化生产乙二醇的过程，其特征在于该过程包括以下三个步骤：(a) 由含有羟基官能化离子液体和碱金属盐的离子液体复合催化剂在水相条件下催化乙烯氧化物和CO2的羰基化步骤，以产生碳酸乙烯酯和乙二醇；(b) 将步骤(a)中获得的含有碳酸乙烯和离子液体复合催化剂的反应溶液与水反应以产生乙二醇的水解步骤；(c) 从含有乙二醇和步骤(b)中产生的催化剂的水溶液中脱水和精制乙二醇的纯化步骤。该过程具有以下优点：催化剂活性高、适用性强、稳定性好，反应条件宽松，乙烯氧化物转化率高，乙二醇选择性高，过程简单。
• 一种羟基化离子液体型水合物抑制剂及其制 备方法
  申请人：中国科学院广州能源研究所

  公开号：CN106831651B

  公开（公告）日：2019-06-11

  本发明公开了一种结构式如式Ⅰ所示的羟基化离子液体型水合物抑制剂，该水合物抑制剂由N‑羟乙基‑N‑甲基哌啶阳离子和阴离子按摩尔比1:1构成；该抑制剂电导率高、热稳定性好、不易挥发、可生物降解、无毒、对环境友好且抑制性能高效，在0.5wt％～3.0wt％的低剂量浓度下可有效抑制水合物生成，试剂成本大大降低，具有广泛的适用性，既可以单独使用，也可以与商用动力学抑制混合使用，具有广阔应用的前景。其中R1为羟乙基，R2为甲基，X‑为Cl‑或者Br‑。
• Antileishmanial Ring-Substituted Ether Phospholipids
  作者：Nikos Avlonitis、Eleni Lekka、Anastasia Detsi、Maria Koufaki、Theodora Calogeropoulou、Efi Scoulica、Eleni Siapi、Ioanna Kyrikou、Thomas Mavromoustakos、Andrew Tsotinis、Simona Golic Grdadolnik、Alexandros Makriyannis

  DOI：10.1021/jm020972c

  日期：2003.2.1

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.
• Design and Synthesis of Potent Antileishmanial Cycloalkylidene-Substituted Ether Phospholipid Derivatives
  作者：Theodora Calogeropoulou、Panagiotis Angelou、Anastasia Detsi、Irene Fragiadaki、Effie Scoulica

  DOI：10.1021/jm701166b

  日期：2008.2.1

  Two series of novel ether phospholipids (EPs) have been synthesized. The first includes cyclodecylideneor cyclopentadecylidene-substituted EPs carrying N,N,N-trimethylammonium or N-methylpiperidino or N-methylmorpholino head groups. The second series encompasses more rigid head groups in combination with cycloalkylidene moieties in the lipid portion. In addition, hydrogenated derivatives were obtained. All the new analogues, except 33, were 1.5- to 62-fold more potent than miltefosine against the intracellular L. infantum, and the most active ones were also less cytotoxic against the human monocytic cell line THP1 and less hemolytic than miltefosine. The analogues that combine high potency with low cytotoxicity and hemolytic activity were 19, 37, 2123, 38, 39, and 40. Cyclopentadecylpentylphosphocholine (38) possesses an IC50 of 0.7 mu M against L. infantum amastigotes and is the least cytotoxic analogue, since it does not present toxicity against THP1 macrophages, even at a concentration that is 800-fold the antiparasitic IC50 value, and does not present significant hemolytic activity.
• Alkyl and Alkoxyethyl Antineoplastic Phospholipids
  作者：Maria Koufaki、Vanessa Polychroniou、Theodora Calogeropoulou、Andrew Tsotinis、Markus Drees、Heiner H. Fiebig、Sophie LeClerc、Hans R. Hendriks、Alexandros Makriyannis

  DOI：10.1021/jm9509152

  日期：1996.1.1

  Two series of phosphodiester ether lipid analogs with (N-methylmorpholino)ethyl or (N-methylpiperidino)ethyl polar head groups and long aliphatic or alkoxyethyl chains in the nonpolar portion of the molecule were synthesized as potential antineoplastic agents. The cytotoxic activity of these compounds (9-19) was evaluated in vitro against a panel of six human tumor xenografts and in two biochemical, mechanism-based screens (cdc2 kinase and cdc25 phosphatase). Analogs 13, 14, 17, and 19 showed activity in the in vitro tests. Specifically, 14 and 17 were more active than the reference compound hexadecylphosphocholine (Miltefosine, He-PC) while 13 and 19 possessed activity similar to that of the control. Of the analogs tested the one with the highest potency and least toxicity (17) has an N-methylpiperidino head group and a C-16 alkyl chain. In the mechanism-based tests 11 showed weak inhibitory activity in the cdc25 phosphatase screen.