1-isobutyl-1,4-diazabicyclo[2.2.2]octan-1-ium bromide | 1185279-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-isobutyl-1,4-diazabicyclo[2.2.2]octan-1-ium bromide
• CAS: 1185279-18-8
• 化学式: Br*C₁₀H₂₁N₂
• 分子量: 249.194
• InChiKey: NONSNVXZNMSMJU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.21
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-isobutyl-1,4-diazabicyclo[2.2.2]octan-1-ium bromide 、 azepane dithiocarbamate(1-) 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到2-(4-isobutylpiperazin-1-yl)ethyl azepane-1-carbodithioate
  参考文献：
  名称：

  通过DABCO键裂解直接合成含二硫代氨基甲酸酯衍生物的哌嗪

  摘要：

  用二硫代氨基甲酸盐裂解DABCO键被用作直接合成途径，用于制备新型的含有二硫代氨基甲酸酯官能团的哌嗪。这种无金属且操作简单的方法可以很好地应用于良率和高选择性。此外，使用季铵化的奎尼丁和双季铵化的DABCO，通过相同的方案成功地制备了含有二硫代氨基甲酸酯基团的取代的双-哌嗪和哌啶。

  DOI：

  10.1016/j.tetlet.2020.152610
• 作为产物：
  描述：

  三乙烯二胺 、 溴代异丁烷 以 乙二醇 为溶剂， 反应 0.5h， 生成 1-isobutyl-1,4-diazabicyclo[2.2.2]octan-1-ium bromide
  参考文献：
  名称：

  1,4-二氮杂双环[2.2.2]辛烷（DABCO）衍生的季铵盐与酚和相关亲核试剂的开环反应。

  摘要：

  1,4-二氮杂双环[2.2.2]辛烷（DABCO）已被评估为合成1-烷基-4-（2-苯氧基乙基）哌嗪及其相关衍生物的原料。我们发现，由DABCO烷基化产生的1-烷基-1,4-二氮杂双环[2.2.2] octan-1-ium盐可在高温下与聚乙二醇（PEG）或二甘醇二甲醚中的多种亲核试剂有效反应，得到亲核开环反应产生的哌嗪产物。发现当使用1-苄基-1,4-二氮杂双环[2.2.2] octan-1-ium盐时，苄基化副反应与较软的亲核试剂有关，而未观察到其他类型的烷基化。一锅法可使用苯酚或其他亲核试剂和DABCO，直接从伯醇，卤代烷或磺酸盐直接合成哌嗪。

  DOI：

  10.1039/c1ob06676e

文献信息

• Polycationic Glycosides
  作者：Robert Engel、Ishrat Ghani、Diego Montenegro、Marie Thomas、Barbara Klaritch-Vrana、Alejandra Castaño、Laura Friedman、Jay Leb、Leah Rothman、Heidi Lee、Craig Capodiferro、Daniel Ambinder、Eva Cere、Christopher Awad、Faiza Sheikh、JaimeLee Rizzo、Lisa-Marie Nisbett、Erika Testani、Karin Melkonian

  DOI：10.3390/molecules16021508

  日期：——

  Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented.

  阳离子脂质早已被认为具有抗菌和抗真菌的作用。此前将阳离子脂质附着到碳水化合物基表面的研究表明，碳水化合物附着的阳离子脂质可能作为抗菌和抗真菌药物。为了理解这种可能性，我们合成了几系列与各种糖苷相连的阳离子脂质，旨在开发符合药物要求的抗微生物剂，特别是要求在非常低的浓度下有效，并且在被治疗的生物体内可降解。我们针对这一目标的初步结果已被呈现。
• Coordinated Anionic Inorganic Module—An Efficient Approach Towards Highly Efficient Blue‐Emitting Copper Halide Ionic Hybrid Structures
  作者：Haibo Li、Yi Lv、Zhennan Zhou、Hua Tong、Wei Liu、Gangfeng Ouyang

  DOI：10.1002/anie.202115225

  日期：2022.2.14

  A novel and facile strategy for the design and synthesis of highly luminescent copper halide hybrid structures by fabricating a coordinated anionic inorganic module in these ionic species is reported. By using this approach, a family of strongly blue-emitting copper halide hybrid ionic structures has been prepared with high internal quantum yields (IQYs) up to 98 %.

  报道了一种通过在这些离子物种中制造配位阴离子无机模块来设计和合成高发光卤化铜杂化结构的新颖而简便的策略。通过使用这种方法，已经制备了一系列强蓝光卤化铜杂化离子结构，其内部量子产率 (IQY) 高达 98%。
• One-pot four-component synthesis of novel isothiourea-ethylene-tethered-piperazine derivatives
  作者：Fatima Hajizadeh、Mohammad M. Mojtahedi、M. Saeed Abaee

  DOI：10.1039/d3ra06678a

  日期：——

  phenylisothiocyanate (PITC) and amines in a one-pot manner to give the target products. Initially, through two parallel nucleophilic paths, DABCO and the secondary amine adds to the alkyl bromide and PITC, respectively. The process is followed by the combination of the two respective intermediates to produce the final products by forming a new C-S bond with the expense of a C-N bond cleavage. Consequently, various

  开发了一种有效的无金属四组分方法，用于合成通过乙烯键连接到异硫脲基团的哌嗪衍生物。DABCO与各种烷基溴反应原位生成1,4-二氮杂双环[2.2.2]辛烷(DABCO)盐，与异硫氰酸苯酯(PITC)和胺类一锅法反应得到目标产物。最初，通过两条平行的亲核路径，DABCO 和仲胺分别加到烷基溴和 PITC 上。该过程随后将两种各自的中间体结合起来，通过形成新的 CS 键（以 CN 键断裂为代价）来生产最终产品。因此，在该方案中各种 DABCO 盐和仲胺具有良好的耐受性，能够以良好的收率提供异硫脲-乙烯-束缚-哌嗪化合物。
• Polycations. 17. Synthesis and properties of polycationic derivatives of carbohydrates
  作者：Marie Thomas、Diego Montenegro、Alejandra Castaño、Laura Friedman、Jay Leb、Mia Lace Huang、Leah Rothman、Heidi Lee、Craig Capodiferro、Daniel Ambinder、Eva Cere、Jessica Galante、JaimeLee Rizzo、Karin Melkonian、Robert Engel

  DOI：10.1016/j.carres.2009.04.021

  日期：2009.9

  In our continuing investigation of polycationic salts for purposes of antimicrobial action, ion-channel blocking, and construction of ionic liquids, we have prepared several series of polycationic salts derived from carbohydrate precursors. These salts are currently being investigated for optimal efficacy as antibacterials and antifungals, as well as for other applications. The syntheses of such series of salts are described here along with preliminary antibacterial testing results and a discussion of their properties indicating their potential utility for several purposes. (C) 2009 Elsevier Ltd. All rights reserved.
• Polycations. 18. The synthesis of polycationic lipid materials based on the diamine 1,4-diazabicyclo[2.2.2]octane
  作者：Robert Engel、JaimeLee Iolani Rizzo、Christina Rivera、Mariah Ramirez、Mia Lace Huang、Diego Montenegro、Craig Copodiferro、Valbona Behaj、Marie Thomas、Barbara Klaritch-vrana、Jeanne Fabian Engel

  DOI：10.1016/j.chemphyslip.2008.12.003

  日期：2009.3

  Herein is reported the preparation of several series of polyammonium salts that serve as cationic lipids or precursors thereof, and are structurally based on the parent diamine 1,4-diazabicyclo[2.2.2]octane (dabco).Through selective alkylation of dabco a variety of di-and tetracationic lipid species and precursors thereof have been prepared. The resultant materials are of significant interest for a variety of purposes, including serving as antimicrobial agents and antihydrophobic species, the details of which are provided in separate reports. (c) 2008 Elsevier Ireland Ltd. All rights reserved.