undec-1-en-11-ylpenta(ethylene glycol) | 130727-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: undec-1-en-11-ylpenta(ethylene glycol)
• 英文别名: 2-[2-[2-[2-(2-undec-10-enoxyethoxy)ethoxy]ethoxy]ethoxy]ethanol
• CAS: 130727-47-8
• 化学式: C₂₁H₄₂O₆
• 分子量: 390.561
• InChiKey: QLLUWSCSZOLBQD-UHFFFAOYSA-N

物化性质

• 沸点：
  471.1±35.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  27.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  undec-1-en-11-ylpenta(ethylene glycol) 在 盐酸 、 偶氮二异丁腈 作用下， 以 甲醇 为溶剂， 反应 126.0h， 生成 (1-mercaptoundec-11-yl)penta(ethylene glycol)
  参考文献：
  名称：

  Formation of self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)mOH on gold

  摘要：

  This paper describes the preparation of oligo(ethylene glycol)-terminated alkanethiols having structure HS-(CH2)11(OCH2CH)m(OH) (m = 3-7) and their use in their use in the formation of self-assembled monolayers (SAMs) on gold. A combination of experimental evidence derived from X-ray photoelectron spectroscopy (XPS), measurement of contact angles, and ellipsometry implies substantial disorder in the oligo(ethylene glycol)-containing segment. The order in the -(CH2)11-group is not defined by the available evidence. The SAMs are moderately hydrophilic: theta-a(H2O) = 34-38-degrees; theta-r(H2O) = 22-25-degrees. A study of monolayers containing mixtures of HS(CH2)11CH3 and HS(CH2)11(OCH2CH2)6OH suggests that the oligo(ethylene glycol) moieties are effective at preventing underlying methylene groups from influencing wetting by water. A limited study demonstrates that these oligo(ethylene glycol)-containing SAMs resist that adsorption of protein from solution and suggests that SAMS will be a useful model system model for studying the adsorption of proteins onto organic surfaces.

  DOI：

  10.1021/ja00001a002
• 作为产物：
  描述：

  羟丙基淀粉磷酸酯 、 11-溴-1-十一烯 在 sodium hydroxide 作用下， 反应 24.0h， 以78%的产率得到undec-1-en-11-ylpenta(ethylene glycol)
  参考文献：
  名称：

  Formation of self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)mOH on gold

  摘要：

  This paper describes the preparation of oligo(ethylene glycol)-terminated alkanethiols having structure HS-(CH2)11(OCH2CH)m(OH) (m = 3-7) and their use in their use in the formation of self-assembled monolayers (SAMs) on gold. A combination of experimental evidence derived from X-ray photoelectron spectroscopy (XPS), measurement of contact angles, and ellipsometry implies substantial disorder in the oligo(ethylene glycol)-containing segment. The order in the -(CH2)11-group is not defined by the available evidence. The SAMs are moderately hydrophilic: theta-a(H2O) = 34-38-degrees; theta-r(H2O) = 22-25-degrees. A study of monolayers containing mixtures of HS(CH2)11CH3 and HS(CH2)11(OCH2CH2)6OH suggests that the oligo(ethylene glycol) moieties are effective at preventing underlying methylene groups from influencing wetting by water. A limited study demonstrates that these oligo(ethylene glycol)-containing SAMs resist that adsorption of protein from solution and suggests that SAMS will be a useful model system model for studying the adsorption of proteins onto organic surfaces.

  DOI：

  10.1021/ja00001a002

文献信息

• Grafting Nitrilotriacetic Groups onto Carboxylic Acid-Terminated Self-Assembled Monolayers on Gold Surfaces for Immobilization of Histidine-Tagged Proteins
  作者：Jungkyu K. Lee、Yang-Gyun Kim、Young Shik Chi、Wan Soo Yun、Insung S. Choi

  DOI：10.1021/jp0378236

  日期：2004.6.1

  In this paper, we report a common intermediate method to present nitrilotriacetic acid (NTA) groups on gold surfaces for immobilizing His-tagged proteins onto the surfaces, and a full characterization of self-assembled monolayers (SAMs) terminating in carboxylic acids [HS(CH2)(15)COOH (C15-COOH), HS(CH2)(11)(OCH2CH2)(3)-OCH2COOH (EG3-COOH), and HS(CH2)(11)(OCH2CH2)(5)OCH2COOH (EG5-COOH)] and coupling reactions of an NTA-containing primary amine [(1S)-N-(5-amino-l-carboxypentyl)iminodiacetic acid; NTA-NH2] with the carboxylic acid on surfaces. The lateral packing densities of the COOH-terminated SAMs were calculated to be 4.32 (for C15-COOH), 3.49 (for EG3-COOH), and 2.65 (for EG5-COOH) molecules/nm(2). The packing densities were decreased by incorporating a relatively flexible ethylene glycol (EG) group into the backbone of alkanethiols and increasing the number of the EG groups in the backbone of alkanethiols. The NTA group was then attached by coupling NTA-NH2 with the COOH group on the surfaces, followed by a Ni(II) complexation. The coupling reaction was characterized by FT-IR spectroscopy, ellipsometry, and XPS, and the coupling efficiency ("yield") was estimated by comparing the experimentally determined N 1s to S 2p (N/S) ratio of XPS data with the N/S ratio calculated for the functionalization of the SAMs presenting NTANi(II): the coupling yields were 30% (for C15-COOH) and 25% (for EG3-COOH and EG5-COOH). Preliminary experiments on the binding of His-tagged proteins onto the surfaces were also performed.