S-(11-hydroxy-undecyl) thioacetate | 73768-96-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-(11-hydroxy-undecyl) thioacetate
• 英文别名: 11-thioacetate undecanol；11-thioacetylundecanol；11-hydroxyundecyl ethanethioate；11-thioacetylundecan-1-ol；thioacetic acid S-(11-hydroxy-undecyl) ester；11-thioacetoxyundecanol；11-Thioacetyl-1-undecanol；S-(11-hydroxyundecyl) ethanethioate
• CAS: 73768-96-4
• 化学式: C₁₃H₂₆O₂S
• 分子量: 246.414
• InChiKey: DKLAOYJVJSWTSI-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C(Solv: hexane (110-54-3))
• 沸点：
  348.7±15.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(11-hydroxy-undecyl) thioacetate 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 sodium thiomethoxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 90.75h， 生成 11-mercapto-undecyl E-3-(4-diethylamino-2-hydroxy-phenyl)propenoate
  参考文献：
  名称：

  Visible Light Excitation of CdSe Nanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands

  摘要：

  The photochemical properties of organic ligands on the surface of nanocrystalline CdSe particles were examined. A number of thiols carrying a substituted cinnamate tail was synthesized. In solution, these cinnamate compounds undergo light-induced ( 374 nm) E-Z isomerization, followed by a nonphotolytic lactonization to give highly fluorescent coumarin. The cinnamate-thiols were successfully exchanged onto the CdSe nanocrystal, and the photochemical behavior of these conjugates was studied. Upon aerobic photolysis at 374 nm, the surface cinnamates released coumarin accompanied by rapid nanocrystal degradation. This degradation was not observed under similar anaerobic conditions or when the organic ligands did not contain the cinnamate group. Surprisingly, very similar results were obtained upon irradiation at visible wavelengths at which the cinnamate has no absorption. With the aid of UV-visible absorption spectroscopy, fluorescence spectroscopy, and electrochemistry, a unified theory for both the increased photoinstability of the nanocrystal as well as the coumarin release was proposed. It involves cinnamate radical anions on the CdSe surface, formed upon electron transfer from the excited nanocrystal to the surface cinnamate, undergoing E-Z isomerization. Practically, this results in the remarkable ability to release coumarin from nanocrystal ligands simply by exciting the nanocrystal with visible light. This new photorelease protocol not only aids in the understanding of fundamental nanocrystal-ligand interactions but may also offer new opportunities in the areas of drug delivery and imaging.

  DOI：

  10.1021/ja063562c
• 作为产物：
  描述：

  1-bromoundecanol 、 potassium thioacetate 以 乙醇 为溶剂， 以53%的产率得到S-(11-hydroxy-undecyl) thioacetate
  参考文献：
  名称：

  一步合成环素的选择性单N-烷基化

  摘要：

  在这封信中，我们描述了使用一系列官能化的烷基卤化物进行的环己酮（1,4,7,10-四氮杂环十二烷）的选择性一步单N-烷基化。这种“易于使用”的合成方法产生了由各种卤代烷形成的环素单衍生物，或者，当使用烷基二卤化物时，产生了双环素衍生物，其中烷基将两个环素大环连接在一起。虽然反应条件要求使用化学计量比为1：4（卤代烷：环烷烃），但任何未反应的环糊精都可以通过水萃取法回收并成功地重复使用。发现该方法是非常通用的，特别适合于带有受保护的硫醇基团以及α-氯酰胺衍生的生色团的循环目标。这种细胞周期垂体生色团被用作镧系元素发光探针和传感器的触角。

  DOI：

  10.1016/j.tetlet.2007.09.022

文献信息

• Gold Glyconanoparticles: Synthetic Polyvalent Ligands Mimicking Glycocalyx-Like Surfaces as Tools for Glycobiological Studies
  作者：África G Barrientos、Jesús M. de la Fuente、Teresa C. Rojas、Asunción Fernández、Soledad Penadés

  DOI：10.1002/chem.200204544

  日期：2003.5.9

  methodology is described for tailoring sugar-functionalised gold nanoclusters (glyconanoparticles) that have 3D polyvalent carbohydrate display and globular shapes. This methodology allows the preparation of glyconanoparticles with biologically significant oligosaccharides as well as with differing carbohydrate density. Fluorescent glyconanoparticles have been also prepared for labelling cells in biological

  描述了一种简单通用的方法，用于定制具有3D多价碳水化合物展示和球状形状的糖官能化金纳米团簇（糖纳米颗粒）。该方法允许制备具有生物学上显着的低聚糖以及具有不同碳水化合物密度的糖纳米颗粒。还已经制备了荧光糖纳米颗粒以在生物测试中标记细胞。该材料是水溶性的，在生理条件下稳定，并且呈现出特别小的芯尺寸。所有这些都已通过（1）NMR，UV和IR光谱，TEM和元素分析进行​​了表征。它们的高度多价网络可以模拟糖鞘脂的聚集和质膜上的相互作用，从而为糖生物学研究提供了可控的系统。此外，
• Organo-soluble photoresponsive azo thiol monolayer-protected gold nanorods
  作者：Jouliana M. El Khoury、Xiaoli Zhou、Liangti Qu、Liming Dai、Augustine Urbas、Quan Li

  DOI：10.1039/b901826c

  日期：——

  Organo-soluble photoresponsive azothiol monolayer-protected gold nanorods were synthesized; the resulting gold nanorods encapsulated by thiols on their entire surface with strong covalent Au–S linkages were very stable in both organic solvents and in the solid state without aggregation or decomposition.

  有机溶剂可溶的光响应性偶氮硫醇单层保护金纳米棒已合成成功；这些整个表面被硫醇包裹并通过强共价Au-S键连接的金纳米棒，在有机溶剂和固态中都非常稳定，不发生聚集或分解。
• Functional aliphatic polyesters and nanoparticles prepared by organocatalysis and orthogonal grafting chemistry
  作者：Angela L. Silvers、Chia-Chih Chang、Todd Emrick

  DOI：10.1002/pola.26114

  日期：2012.9.1

  used for postpolymerization modification of diblock copolymers possessing alkene groups on one block and alkyne groups on the other block. The polyesters were crosslinked using azide/alkyne cycloaddition, by reaction of α,ω‐diazides with the pendent alkynes on the polyester backbone. This gave polyester nanoparticles possessing alkene functionality, which were subjected to further modification using thiol‐ene

  我们描述了将有机催化用于官能化内酯的开环聚合以及将所得脂肪族聚酯转化为带有可进一步修饰的附加官能团的交联纳米颗粒的方法。具体来说，通过1,5,7-三氮杂双环[4.4.0] dec-5-烯催化制备高官能度的脂肪族聚酯均聚物以及无规和嵌段共聚物，得到带有侧链和炔基的聚酯。叠氮化物炔炔点击和硫醇烯化学用于二嵌段共聚物的后聚合改性，该嵌段共聚物在一个嵌段上具有烯烃基，在另一个嵌段上具有炔基。聚酯通过叠氮化物/炔烃环加成反应，通过α，ω-二叠氮化物与聚酯骨架上的侧链炔反应而交联。这产生了具有烯烃官能度的聚酯纳米颗粒，使用硫醇烯反应对其进行了进一步修饰以引入其他官能度。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年
• An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates
  作者：Slawomir Lach、Sebastian Demkowicz、Dariusz Witt

  DOI：10.1016/j.tetlet.2013.10.056

  日期：2013.12

  We have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives 1 with functionalized alkyl thiolate anions, generated in situ from thioacetates 2 and sodium methoxide or butylamine. The developed

  我们已经开发了在温和条件下以非常高的收率合成功能化不对称二烷基二硫化物的便捷方法。设计的方法基于（5,5-二甲基-2-硫代氧杂1,3,2-二氧杂磷酰氨基-2-基）-二硫烷基衍生物1与硫代乙酸酯2和钠的原位生成的官能化硫代烷基磺酸盐的反应甲醇或丁胺。所开发的方法允许制备带有其他羟基，羧基，氨基，叠氮基，生物素或马来酰亚胺官能团的不对称二硫键。
• AuBr3 mediated glycosidations: synthesis of tetrasaccharide motif of the Leishmania donovani lipophosphoglycan
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1007/s10719-012-9400-7

  日期：2012.5

  Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr3 mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via ‘click’ reaction.

  在导致内脏利什曼病的唐氏利什曼原虫脂磷聚糖中存在的四糖帽被合成为完全保护的丙炔糖苷。在丙炔糖苷存在的情况下，采用 AuBr3 介导的丙炔 1,2-orthoester 选择性糖基化是获得含丙炔的低聚物的关键步骤。此外，丙炔四糖通过 "点击 "反应与位于两个末端的含有叠氮硫醇官能团的长链碳氢化合物连接。