3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid | 916441-89-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid
• 英文别名: 3-[Tert-butyl(dimethyl)silyl]oxy-5-dodecoxy-5-oxopentanoic acid；3-[tert-butyl(dimethyl)silyl]oxy-5-dodecoxy-5-oxopentanoic acid
• CAS: 916441-89-9
• 化学式: C₂₃H₄₆O₅Si
• 分子量: 430.701
• InChiKey: JXMQRDAPFNGSHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid 在 吡啶 、 四丁基氟化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 8.66h， 生成
  参考文献：
  名称：

  古菌脂质的跨膜大环双亲脂质模拟物

  摘要：

  72 元大环四酯双亲分子的合成是通过六个化学步骤从市售的起始材料中完成的，使用铜加速叠氮化物-炔烃偶联以高产率闭合大环。还制备了相关的二酯两亲物和无环四酯双亲物。带有硝基苯基磷酸酯头部基团的一组脂质被掺入磷脂囊泡中，但在碱性条件下不能进行磷酸酯水解，在竞争中被有效消除。带有磷酸盐连接的硝基苯并恶二唑 (NBD) 头部基团的相同脂质核心也结合到磷脂囊泡中，并且 NBD 荧光被钴离子淬灭。跨膜双亲分子的比例由存在和不存在去污剂时钴淬灭的比率确定。大环 bolaamphiphile 结合到磷脂囊泡中，使得 48 ± 4% 的 NBD 头基位于外层...

  DOI：

  10.1139/cjc-2016-0252
• 作为产物：
  描述：

  十二烷醇 、 3-叔丁基二甲硅氧基戊二酸酐 以 甲苯 为溶剂， 反应 24.0h， 以95%的产率得到3-(tert-butyldimethylsilyloxy)-5-oxo-5-(dodecyloxy)pentanoic acid
  参考文献：
  名称：

  古菌脂质的跨膜大环双亲脂质模拟物

  摘要：

  72 元大环四酯双亲分子的合成是通过六个化学步骤从市售的起始材料中完成的，使用铜加速叠氮化物-炔烃偶联以高产率闭合大环。还制备了相关的二酯两亲物和无环四酯双亲物。带有硝基苯基磷酸酯头部基团的一组脂质被掺入磷脂囊泡中，但在碱性条件下不能进行磷酸酯水解，在竞争中被有效消除。带有磷酸盐连接的硝基苯并恶二唑 (NBD) 头部基团的相同脂质核心也结合到磷脂囊泡中，并且 NBD 荧光被钴离子淬灭。跨膜双亲分子的比例由存在和不存在去污剂时钴淬灭的比率确定。大环 bolaamphiphile 结合到磷脂囊泡中，使得 48 ± 4% 的 NBD 头基位于外层...

  DOI：

  10.1139/cjc-2016-0252

文献信息

• Solid-phase synthesis of a library of linear oligoester ion-channels
  作者：Thomas Murray Fyles、Horace Luong

  DOI：10.1039/b816648j

  日期：——

  A solid-phase synthesis protocol was used to prepare fifteen new linear tetra-, and penta-esters structurally related to an active lead compound. The structures were assembled from three types of hydroxyl protected building blocks: monoalkyl esters of hydroxyglutaric acid, ω-hydroxyacids, and α-hydroxymethylalkanoic acids. The standard methodology gave acceptable quantities of material free of small molecule impurities. Mass spectrometric analysis revealed the presence of deletions due to incomplete coupling, as well as additions and macrolactones due to partial acidic rearrangement on release from the solid-support. The amount of these impurities could be estimated from the 1H NMR spectra, and their implications for subsequent activity analysis are discussed.

  采用固相合成协议制备了十五种新的线性四酯和五酯，这些化合物的结构与一种活性先导化合物相关。结构由三种类型的羟基保护构建块组装而成：羟基戊二酸的单烷基酯、ω-羟基酸和α-羟基甲基烷酸。标准方法得到了数量可接受、未含小分子杂质的材料。质谱分析揭示了因耦合不完全而导致的缺失，以及因从固体支持释放后的部分酸重排而引起的附加物和大环内酯的存在。通过1H NMR光谱可以估计这些杂质的数量，并讨论它们对后续活性分析的影响。
• Synthesis, transport activity, membrane localization, and dynamics of oligoester ion channels containing diphenylacetylene units
  作者：Joanne M. Moszynski、Thomas M. Fyles

  DOI：10.1039/c0ob00194e

  日期：——

  Four new linear oligoesters containing a diphenylacetylene unit were prepared by fragment coupling sequences and the ion channel forming ability of the compounds was investigated. Activity in vesicles was very strongly controlled by overall length; the longest compound was effectively inactive. Planar bilayer studies established that all compounds are able to form channels, but that regular step changes in conductance depend on the location of the diphenylacetylene unit within the oligoester and on the electrolyte. The intrinsic fluorescence of the diphenylacetylene unit was used to probe aggregation and membrane localization. Both monomer (320 nm) and excimer (380 nm) emissions are quenched by copper ions; quenching of the excimer emission from an aqueous aggregate is very efficient. Time-dependent changes in the intensities of monomer and excimer emission show slow transfer of diphenylacetylene units from an aqueous aggregate to a membrane-bound monomer with subsequent growth of emission from a membrane-bound excimer. The latter species is not quenched by aqueous copper ions. The implications of these species and processes for the mechanism of ion channel formation by simple oligoesters are discussed.

  制备了四种新型线性寡聚酯，其中包含二苯乙炔单元，并研究了这些化合物的离子通道形成能力。囊泡中的活性受到整体长度的强烈影响；最长的化合物几乎是非活性的。平面双层研究表明，所有化合物都能够形成通道，但导电性发生规律性阶跃变化取决于二苯乙炔单元在寡聚酯中的位置以及电解质的影响。利用二苯乙炔单元的内在荧光来探测聚集和膜定位。单体（320nm）和激基（380nm）发射均被铜离子猝灭；来自水相聚集体的激基发射被猝灭的效果非常显著。单体和激基发射强度的时间依赖变化表明，二苯乙炔单元从水相聚合物缓慢转移到膜结合的单体中，随后膜结合的激基发射逐渐增强。后者物种不受水相铜离子的猝灭。这些物种和过程对简单寡聚酯形成离子通道机制的影响进行了讨论。
• Solid-Phase Synthesis of Oligoester Ion Channels
  作者：Thomas M. Fyles、Chi-Wei Hu、Horace Luong

  DOI：10.1021/jo0615753

  日期：2006.10.1

  A simple synthesis of oligoesters from TBDMS-protected-beta- and THP-protected-omega-hydroxycarboxylic acids using a solid-phase synthesis protocol is reported. Procedures were optimized for the efficient production of ion channel candidates in high purity with minimal purification. The product oligoesters were evaluated for ion transport activity using a fluorescent dye/vesicle assay. Oligoesters produced by this strategy show structure-dependent activity; the most active compounds are closely comparable to previously known oligoesters, but are available at a fraction of the synthetic effort.
• A membrane-spanning macrocyclic bolaamphiphile lipid mimic of archaeal lipids
  作者：Gavin M. Mitchell、Amelia Hesketh、Christie Lombardi、Cally Ho、Thomas M. Fyles

  DOI：10.1139/cjc-2016-0252

  日期：2017.3

  in six chemical steps from commercially available starting materials using copper-accelerated azide–alkyne coupling to close the macrocycle in high yield. Related diester amphiphiles and an acyclic tetraester bolaamphiphile were also prepared. The set of lipids bearing nitrophenyl phosphate head groups were incorporated into phospholipid vesicles but failed to undergo phosphate hydrolysis in basic conditions

  72 元大环四酯双亲分子的合成是通过六个化学步骤从市售的起始材料中完成的，使用铜加速叠氮化物-炔烃偶联以高产率闭合大环。还制备了相关的二酯两亲物和无环四酯双亲物。带有硝基苯基磷酸酯头部基团的一组脂质被掺入磷脂囊泡中，但在碱性条件下不能进行磷酸酯水解，在竞争中被有效消除。带有磷酸盐连接的硝基苯并恶二唑 (NBD) 头部基团的相同脂质核心也结合到磷脂囊泡中，并且 NBD 荧光被钴离子淬灭。跨膜双亲分子的比例由存在和不存在去污剂时钴淬灭的比率确定。大环 bolaamphiphile 结合到磷脂囊泡中，使得 48 ± 4% 的 NBD 头基位于外层...