11-（乙酰硫基）十一酸-d20 | 6974-31-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 11-（乙酰硫基）十一酸-d20
• 英文名称: 11-(acetylthio)undecanoic acid
• 英文别名: 11-(Acetylsulfanyl)undecanoic acid；11-acetylsulfanylundecanoic acid
• CAS: 6974-31-8
• 化学式: C₁₃H₂₄O₃S
• 分子量: 260.398
• InChiKey: DHKWYRRJFXRZOA-UHFFFAOYSA-N

物化性质

• 熔点：
  57.5-58.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  393.4±15.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  11-（乙酰硫基）十一酸-d20 在 双氧水 、 溶剂黄146 作用下， 生成 11-sulfonic undecanoic acid
  参考文献：
  名称：

  Preparation of Sulfonic Acids from Unsaturated Compounds¹

  摘要：

  DOI：

  10.1021/jo01055a031
• 作为产物：
  描述：

  1,11-十一烷二醇 在 chromium(VI) oxide 、 氢溴酸 作用下， 以 正辛烷 为溶剂， 生成 11-（乙酰硫基）十一酸-d20
  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

• Sodium Borohydride–Mediated Transesterification
  作者：Grigoriy Sereda、Swetha Pothula、James Dreessen

  DOI：10.1080/00397910903072438

  日期：2010.4.12

  presence of sodium borohydride, esters react with alcohols with formation of the corresponding esters. The reaction is sensitive to the solvent, structure of the ester, and is often concurrent with reduction. Thioesters containing an ester group can be selectively cleaved by the reagent. Both esters and thioesters attached to solid support are resistant toward sodium borohydride. The in situ prepared

  在硼氢化钠存在下，酯与醇反应形成相应的酯。该反应对溶剂、酯的结构敏感，并且通常与还原同时发生。含有酯基的硫酯可以被试剂选择性地裂解。附着在固体支持物上的酯和硫酯都耐硼氢化钠。引入原位制备的四烷氧基硼酸钠作为酯交换的有效试剂和催化剂。
• Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
  作者：Jie Luo、Michael Rauch、Liat Avram、Yehoshoa Ben-David、David Milstein

  DOI：10.1021/jacs.0c10884

  日期：2020.12.30

  Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex

  硫酯与 H2 的直接氢化提供了一种简便且无废物的方法来获得醇和硫醇。然而，没有记录该反应的报告，可能是因为生成的硫醇与典型的氢化催化剂不相容。在这里，我们报告了硫酯的有效和选择性氢化。该反应由无添加剂的吖啶基钌配合物催化。各种硫酯被完全氢化成相应的醇和硫醇，对酰胺、酯和羧酸基团具有优异的耐受性。硫代氨基甲酸酯和硫代酰胺也在类似条件下进行氢化，大大扩展了有机硫化合物氢化的应用。
• A photolabile protection strategy for terminal alkynes
  作者：Tina A. Gschneidtner、Kasper Moth-Poulsen

  DOI：10.1016/j.tetlet.2013.07.144

  日期：2013.10

  Several photo-caged alcohols were synthesized via mild copper(II)-catalyzed substitution between tertiary propargylic alcohols and 2-nitrobenzyl alcohol to build up robust, base stable o-nitrobenzyl (NB) photo-cleavable compounds. We compare the new photolabile protecting group with the commonly used alkyne protecting group, 2-methyl-3-butyn-2-ol and the results show that NB ethers are stable under the

  我们提出了一种对末端炔烃进行光不稳定保护的策略。通过在叔炔丙醇和2-硝基苄醇之间的轻度铜（II）催化取代反应合成了几种光笼蔽的醇，以建立坚固的，碱稳定的邻硝基苄基（NB）可光裂解的化合物。我们将新的光不稳定保护基团与常用的炔烃保护基团2-甲基-3-丁炔-2-醇进行了比较，结果表明，NB醚在裂解条件下对甲基丁炔醇保护的炔烃的裂解是稳定的。另外，我们提出了含有硫醇基团的光可裂解的NB衍生物的合成，该衍生物可以用作光诱导的表面官能化反应的试剂。
• Scope and limitations of ruthenium-catalyzed metathesis of simple polymer-bound alkenes
  作者：Peter G Breed、James A Ramsden、John M Brown

  DOI：10.1139/v01-045

  日期：2001.5.1

  Synthetic procedures for the preparation of two types of functional resin are described, both based on 2% cross-linked polystyrene with a high density (>60%) of side-chains and terminated by a primary alcohol. In the first case the C₁₁ side-chain is linked to the polymer through a sulfide, and in the second an ether linkage is employed to incorporate a (CH₂CH₂O)₄ unit. In both cases the resins have ¹³C NMR spectra that are informative in the chain terminus region without special operating conditions. Model intermolecular metathesis reactions were carried out on allylcarbamic acid tert-butyl ester and various alkenes with Grubbs' catalyst. On the basis of these experiments, gel-phase metathesis was successfully demonstrated between a polymer-bound allyl ether and simple symmetrical disubstituted alkenes, monitoring the extent of reaction by ¹³C NMR. These reactions did not go to completion even with recycling and some evidence for competing interchain metathesis is presented, based on the increased broadening and reduced mobility of the ensuing polymer.Key words: alkene metathesis, ruthenium, gel-phase, ¹³C NMR.

  合成两种功能树脂的制备方法被描述，两种树脂均基于2%交联聚苯乙烯，具有高密度（>60%）的侧链，并以一次醇为终止基团。在第一种情况下，C11侧链通过硫醚与聚合物连接，而在第二种情况下，采用醚键连接以包含一个（CH2CH2O）4单元。在这两种情况下，树脂具有13C NMR谱，在不需要特殊操作条件下，这些谱在链末端区域提供了信息。对烯丙基氨基甲酸叔丁酯和各种烯烃与Grubbs催化剂进行了模型分子间重排反应。基于这些实验，成功地展示了聚合物结合的烯丙基醚与简单对称二取代烯烃之间的凝胶相重排反应，并通过13C NMR监测反应程度。这些反应即使进行回收也没有完全进行，同时提供了一些竞争性链间重排反应的证据，这是基于随后聚合物的增加变宽和减少流动性。关键词：烯烃重排反应，钌，凝胶相，13C NMR。
• Gold nanoparticles functionalised with fast water exchanging Gd³⁺ chelates: linker effects on the relaxivity
  作者：Miguel F. Ferreira、Janaina Gonçalves、Bibimaryam Mousavi、Maria I. M. Prata、Sérgio P. J. Rodrigues、Daniel Calle、Pilar López-Larrubia、Sebastian Cerdan、Tiago B. Rodrigues、Paula M. Ferreira、Lothar Helm、José A. Martins、Carlos F. G. C. Geraldes

  DOI：10.1039/c4dt03210a

  日期：——

  great potential for further investigation as MRI contrast agents. This study contributes to a better understanding of the effect of linker length on the relaxivity of gold nanoparticles functionalized with Gd3+ complexes. It is a relevant contribution towards “design rules” for nanostructures functionalized with Gd3+ chelates as Contrast Agents for MRI and multimodal imaging.

  固定在金纳米颗粒上的Gd 3+螯合物显示出的弛豫性是纳米颗粒大小，水交换速率和螯合物结构之间复杂相互作用的结果。在这项工作中，我们研究了ω-硫代烷基接头的长度，将快速交换水的Gd 3+螯合物固定在金纳米颗粒上对固定螯合物的弛豫性的影响。制备了用巯基癸酸的Gd 3+螯合物和DO3A - N-（α-氨基）丙酸酯螯合剂的脂酰酰胺共轭物官能化的金纳米颗粒，并将其作为MRI的潜在CA。每个螯合物的高弛豫度，数量级为28–38 mM -1 s -1（30 MHz，25°C），得益于同时优化了旋转相关时间和水交换速率。固定螯合剂围绕连接接头的快速局部旋转运动（内部柔韧性）仍然限制了可达到的松弛度。固定的螯合物的内部柔韧性程度似乎与连接接头的长度无关。小鼠的生物分布和MRI研究表明，金纳米颗粒的体内行为主要由大小决定。较小的纳米颗粒（HD = 3.9 nm）经历快速的肾脏清除和避免RES器官，而较大的纳米颗粒（HD