乙醇,2-[2-[2-[(苯基甲基)硫代]乙氧基]乙氧基]- | 187279-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙醇,2-[2-[2-[(苯基甲基)硫代]乙氧基]乙氧基]-
• 英文名称: 2-{2-[2-(benzylsulfanyl)ethoxy]ethoxy}ethanol
• 英文别名: 2-[2-(2-benzylsulfanylethoxy)ethoxy]ethanol；8-benzylthio-3,6-dioxaoctanol
• CAS: 187279-51-2
• 化学式: C₁₃H₂₀O₃S
• 分子量: 256.366
• InChiKey: PKRVNDXFEIDFDG-UHFFFAOYSA-N

物化性质

• 沸点：
  397.5±32.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇,2-[2-[2-[(苯基甲基)硫代]乙氧基]乙氧基]- 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 camphor-10-sulfonic acid 、 D(+)-10-樟脑磺酸 、 四丁基硫酸氢铵 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 167.0h， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (1-phenyl-5,8,11,14,17,20,23,26,29,32,35-undecaoxa-2-thiaheptatriacontan-37-yl)carbamate
  参考文献：
  名称：

  The design and synthesis of simple molecular tethers for binding biomembranes to a gold surface

  摘要：

  Molecular tethers have been synthesised for fixing biomembranes to a gold surface. These are comprised of a thiol at one end to bind to the gold, a polyethylenoxy chain of defined length (two, six or twelve ethylenoxy units) in the middle and a cholesteryl residue at the other end to insert into the biomembrane. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00698-4
• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 、 苄硫醇 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以90%的产率得到乙醇,2-[2-[2-[(苯基甲基)硫代]乙氧基]乙氧基]-
  参考文献：
  名称：

  Carbohydrate–protein interactions at interfaces: synthesis of thiolactosyl glycolipids and design of a working model for surface plasmon resonance

  摘要：

  用于碳水化合物-蛋白质结合研究的硫代半乳糖脂已经合成。其中一种代表被选用于与植物凝集素RCA120（蓖麻的凝集素）结合的研究。使用BIAcore表面等离子共振仪器实时定量测量了相互作用。用β-半乳糖苷酶从硫代半乳糖脂中原位去除大部分半乳糖表明凝集素结合具有高度特异性。1-{2-[2-(2-[β-D-半乳糖基-(1 → 4)-1-硫代-β-D-吡喃葡萄糖基]乙氧基)乙氧基]乙氧基}十八烷30的解离常数KD=8.77×10-8 M，比溶液中与乳糖结合的解离常数高四个数量级。需要浓度大于80mM的乳糖才能阻止凝集素与新膜中的硫代半乳糖脂结合。

  DOI：

  10.1039/b210672h

文献信息

• Carbohydrate–protein interactions at interfaces: comparison of the binding of Ricinus communis lectin to two series of synthetic glycolipids using surface plasmon resonance studies
  作者：P. Critchley、G. J. Clarkson

  DOI：10.1039/b306784j

  日期：——

  Two C-lactosyl lipids and the related C-galactosyl lipids have been synthesised and their binding to RCA120 plant lectin was compared with a second series of thiolactosylethoxyalkanes. The interactions were measured quantitatively in real time by surface plasmon resonance (BIAcore) at a range of concentrations and temperatures from 5 to 30 °C. The C-galactosyl lipid (1,3-dimethyl-5-[β-D-galactopyranosyl]-5-(4-octadecyloxybenzyl)pyrimidine-2,4,6-trione) bound much more weakly with a KA = 8.86 × 105 than the corresponding C-lactosyl lipid (1,3-dimethyl-5-[β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl]-5-(4-octadecyloxybenzyl)pyrimidine-2,4,6-trione) (KA = 2.31 × 107). The influence of the linker region of the two different series of lactosyl lipids was clearly demonstrated by the differences in the binding to RCA120 lectin. The changes in kinetic values and in the enthalpic and entropic contribution to the free energy of binding reflected the importance of the linker and the hydrocarbon anchor holding the synthetic glycolipids in the neomembrane.

  合成了两种C-乳糖脂和相关的C-半乳糖脂，并将它们与RCA120植物凝集素的结合情况与第二系列的硫乳糖乙氧烷进行比较。通过表面等离子共振（BIAcore）在5至30°C范围内的不同浓度和温度下实时定量测量了互动。C-半乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）与RCA120的结合明显较弱，结合常数KA = 8.86 × 10^5，远低于相应的C-乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基-(1→4)-β-D-葡萄糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）（KA = 2.31 × 10^7）。两种不同系列乳糖脂的连接区域对RCA120凝集素结合的影响清晰可见，结合的动力学值以及自由能中焓和熵的变化反映了连接器及持有合成糖脂在新膜中的烃锚的重要性。
• Synthesis of a Potential 10E4 Tetrasaccharide Antigen Involved in Scrapie Pathogenesis
  作者：Pascal Bindschädler、Christian Noti、Eva Castagnetti、Peter H. Seeberger

  DOI：10.1002/hlca.200690234

  日期：2006.11

  To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2 + 2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biological role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using

  为了检验四糖3参与瘙痒病发病机理的假说，合成了在还原端用胺连接基官能化的四糖衍生物32。选择（2 + 2）糖基化方法以完全保护的形式提供目标化合物。为了研究其生物学作用，使用Traut试剂将四糖32进一步官能化为相应的硫醇33。在合成过程中，N，N-二乙酰基保护基被证明对自由基和酸性条件不稳定。
• Improved Preparation and Application of Poly(Ethylene Glycol) Vinyl Sulfone
  作者：Afzal Khan、Andrew Marsh

  DOI：10.1080/00397910008087425

  日期：2000.7

  An improved synthesis of poly(ethylene glycol) vinyl sulfone is presented and its reactions with nucleophiles reported.
• Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes
  作者：Matthew R. Hicks、Atvinder K. Rullay、Rosa Pedrido、David H. Crout、Teresa J. T. Pinheiro

  DOI：10.1080/00397910802213794

  日期：2008.10.22

  We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.
• N,N′-Disuccinimidyl carbonate as a coupling agent in the synthesis of thiophospholipids used for anchoring biomembranes to gold surfaces
  作者：Neville Boden、Richard J. Bushby、Quanying Liu、Stephen D. Evans、A.Toby A. Jenkins、Peter F. Knowles、Robert E. Miles

  DOI：10.1016/s0040-4020(98)00674-7

  日期：1998.9

  N,N'-Disuccinimidyl carbonate has been used to couple diacylglycerophosphatidylethanolamine with bis-omega-hydroxypolyethylenoxydisulfide. The resultant thiophospholipids can be used for anchoring biomembranes to gold surfaces. (C) 1998 Elsevier Science Ltd. All rights reserved.