12-(acetylthio)dodecanoic acid | 352439-40-8

• 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: 12-(acetylthio)dodecanoic acid
• 英文别名: 12-Acetylsulfanyldodecanoic acid
• CAS: 352439-40-8
• 化学式: C₁₄H₂₆O₃S
• 分子量: 274.425
• InChiKey: UDIHINGPFGORMG-UHFFFAOYSA-N

物化性质

• 沸点：
  406.8±18.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-(acetylthio)dodecanoic acid 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以85%的产率得到12-巯基癸酸
  参考文献：
  名称：

  A bola-phospholipid bearing tetrafluorophenylazido chromophore as a promising lipid probe for biomembrane photolabeling studies

  摘要：

  为了通过光标记方法研究生物膜，我们合成了一种在跨膜二酰链中间带有四氟苯基叠氮发色团的波拉磷脂探针，并对其进行了表征。该探针显示了波拉脂在巨囊形成过程中的稳定性优势，以及四氟苯叠氮发色团带来的优异光化学特性，因此是一种很有希望用于生物膜光标记研究的探针。

  DOI：

  10.1039/c3ob40659h
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 chromium(VI) oxide 作用下， 生成 12-(acetylthio)dodecanoic acid
  参考文献：
  名称：

  Multiple Electron Tunneling Paths across Self-Assembled Monolayers of Alkanethiols with Attached Ruthenium(II/III) Redox Centers

  摘要：

  Alkanethiol monolayers with pendant redox centers are deposited on gold electrolytes by self-assembly. The monolayers are composed of both an electroactive thiol, HS(CH2)(n)C(O)NHCH(2)pyRu(NH3)(5)(2+/3+), with 10-15 methylene groups, and a diluent thiol, HS(CH2)mCoOH, also with 10-15 methylene groups. The monolayers are classified as ''matched'' (n = m), ''exposed'' (n = 15, m = 10-14), and ''buried'' (n = 10, m = 11-15) according to the relative position of the redox center. Cyclic voltammograms in aqueous Na2SO4 indicate that the monolayers are close-packed with the redox centers residing in the aqueous phase in all but the most buried cases. Measurements of electron transfer kinetics by several methods (cyclic voltammetry, ac impedance spectroscopy, chronoamperometry) yield an internally consistent set of kinetic parameters, the standard rate constant k degrees, and the reorganization energy lambda of the redox centers. The reorganization energies are in good agreement with the theoretically predicted value of 1.0 eV for the pyRu(NH3)(5) redox centers. Plots of ln(k degrees) vs m are linear in all three cases. The slopes of the linear regression fit provide tunneling parameters (beta, where k degrees approximate to e(-beta m)) of 0.97 +/- 0.03 (matched cases), 0.83 +/- 0.03 (exposed cases) and 0.16 +/- 0.02 (buried cases) per methylene. This pattern of beta's is interpreted in terms of electronic coupling between the redox center and the electrode via both the redox thiol and the proximate diluent thiols, with the coupling via the diluent thiols dominating in the exposed cases.

  DOI：

  10.1021/jp962831q

文献信息

• Carboxylate−Imidazole Cooperativity in Dipeptide-Functionalized Gold Nanoparticles with Esterase-like Activity
  作者：Paolo Pengo、Stefano Polizzi、Lucia Pasquato、Paolo Scrimin

  DOI：10.1021/ja043547c

  日期：2005.2.1

  We report here the first example of peptide-functionalized gold nanoparticles hydrolytically active against carboxylate esters. The active units are constituted by His-Phe-OH terminating thiols. The confinement of the catalytic units in the monolayer covering the nanoparticles triggers a cooperative hydrolytic mechanism operative at pH < 7 in which a carboxylate and an imidazolium ion act as general

  我们在这里报告了第一个对羧酸酯具有水解活性的肽官能化金纳米粒子的例子。活性单元由His-Phe-OH封端硫醇构成。催化单元在覆盖纳米颗粒的单层中的限制触发了在 pH < 7 时起作用的协同水解机制，其中羧酸盐和咪唑鎓离子分别充当一般碱和一般酸。类似的单体二肽不存在这种机制，这导致在功能性纳米粒子存在的情况下，在低 pH 值下水解过程的速率加速超过 300 倍。
• Synthesis of a Series of Oligo(ethylene glycol)-Terminated Alkanethiol Amides Designed to Address Structure and Stability of Biosensing Interfaces
  作者：Sofia Svedhem、Carl-Åke Hollander、Jing Shi、Peter Konradsson、Bo Liedberg、Stefan C. T. Svensson

  DOI：10.1021/jo0012290

  日期：2001.6.1

  oligo(ethylene glycols) with up to 12 units were prepared. Selective monoacylation of the symmetrical tetra- and hexa(ethylene glycol) diols as their mesylates with the use of silver(I) oxide was performed. The synthetic approach was based on carbodiimide couplings of various oligo(ethylene glycol) derivatives to omega-(acetylthio) carboxylic acids via a terminal amino or hydroxyl function. SAM structures on gold

  一系列密切相关的寡聚（乙二醇）末端链烷硫醇酰胺（主要是HS（CH（2））（m）CONH（CH（2）CH（2）O）（n）H; m的合成策略＝ 2、5、11、15，n ＝ 1、2、4、6、8、10、12），并且已经开发出类似的酯。制备这些化合物是为了研究金上自组装单分子膜（SAMs）的结构和稳定性，以期设计出新的生物传感界面。为此，制备了具有多达12个单元的单分散性杂官能低聚（乙二醇）。使用氧化银（I）对对称的四和六（乙二醇）二醇作为甲磺酸酯进行选择性单酰化。合成方法基于各种低聚（乙二醇）衍生物的碳二亚胺通过末端氨基或羟基官能团与ω-（乙酰硫基）羧酸的偶联。研究了金的SAM结构的厚度，润湿性（水接触角约为30度）和构象。对于单层厚度（d）与低聚（乙二醇）链中单元数（n）之间的关系，获得了很好的拟合：d = 2.8n + 21.8（A）。有趣的是，相应的红外光谱分析表明寡聚链的构象从全反式（n =
• Novel Versatile Fullerene Synthons
  作者：Konstantinos Kordatos、Tatiana Da Ros、Susanna Bosi、Ester Vázquez、Massimo Bergamin、Claudia Cusan、Federica Pellarini、Véronique Tomberli、Benedetta Baiti、Davide Pantarotto、Vasilios Georgakilas、Giampiero Spalluto、Maurizio Prato

  DOI：10.1021/jo015608k

  日期：2001.7.1

  We report the synthesis of three novel, versatile fullerene intermediates whose main feature is the presence of an amino end group. Simple condensation reactions of these intermediates under standard conditions produce new derivatives that are useful for applications in materials science and medicinal chemistry.

  我们报告了三种新颖，通用的富勒烯中间体的合成，其主要特征是氨基端基的存在。这些中间体在标准条件下的简单缩合反应会产生新的衍生物，可用于材料科学和药物化学中。
• Thermoresponsive Supramolecular Polymer Network Comprising Pyrene-Functionalized Gold Nanoparticles and a Chain-Folding Polydiimide
  作者：Rajendran Vaiyapuri、Barnaby W. Greenland、Stuart J. Rowan、Howard M. Colquhoun、Joanne M. Elliott、Wayne Hayes

  DOI：10.1021/ma300796w

  日期：2012.7.10

  A thermoresponsive, supramolecular nanocomposite has been prepared by the addition of pyrenyl functionalized gold nanoparticles (AuNPs) to a polydiimide that contains receptor residues designed to form defined complexes with pyrene. The novel pyrenyl-functionalized AuNPs (P-AuNPs) were characterized by transmission electron microscopy, with surface functionalization confirmed by infrared and UV–visible

  通过将pyr烯基官能化的金纳米颗粒（AuNPs）添加到聚二酰亚胺中来制备热响应性超分子纳米复合材料，该聚二酰亚胺包含旨在与pyr形成确定的络合物的受体残基。新型pyr基官能化的AuNPs（P-AuNPs）通过透射电子显微镜进行了表征，其表面功能化已通过红外和紫外可见光谱分析得到了证实。P-AuNPs和π电子缺陷的聚二酰亚胺的混合溶液导致形成电子互补，链折叠和π-π堆积的复合物，因此提供了从溶液中沉淀出来的新的超分子纳米复合物网络。P-AuNP通过π-π堆积相互作用与聚二酰亚胺结合，形成超分子交联。紫外可见光谱分析证实了络合过程的热可逆性，并使用透射电子显微镜（TEM），红外光谱（IR）和差示扫描量热法（DSC）表征了超分子-纳米复合材料。超分子聚合物网络在室温下不溶，但在高于60°C的温度下可能会溶解。该系统的热可逆性在五个加热/冷却循环中得以保持，而不会降低网络特性。与单个组分相比，纳米
• Synthesis of Conjugated Diacetylene, Metal-Chelating Monomers for Polymerizable Monolayer Assemblies
  作者：Bidhan C. Roy、Sanku Mallik

  DOI：10.1021/ol015931+

  日期：2001.6.1

  [GRAPHICS]Self-assembled monolayers (SAMs) of thiols on gold have been used for numerous applications. For protein targeting applications, one successful strategy is to use a metal chelating SAM. It has also been demonstrated that polymerized SAMs are much more stable than non polymerized counterparts. We report herein, the synthesis of several polymerizable, metal-chelating thiols capable of complexing luminescent lanthanide ions.