(2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester | 716339-44-5

• 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: (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester
• CAS: 716339-44-5
• 化学式: C₂₅H₄₈O₇S
• 分子量: 492.718
• InChiKey: FOCAKXJOUKQPIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  33.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以78%的产率得到(2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid
  参考文献：
  名称：

  Grafting Nitrilotriacetic Groups onto Carboxylic Acid-Terminated Self-Assembled Monolayers on Gold Surfaces for Immobilization of Histidine-Tagged Proteins

  摘要：

  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.

  DOI：

  10.1021/jp0378236
• 作为产物：
  描述：

  2-{2-[2-(10-十一碳烯-1-基氧基)乙氧基]乙氧基}乙醇 在 4,4'-偶氮双(4-氰基戊酸) 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 (2-{2-[2-(11-Acetylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Grafting Nitrilotriacetic Groups onto Carboxylic Acid-Terminated Self-Assembled Monolayers on Gold Surfaces for Immobilization of Histidine-Tagged Proteins

  摘要：

  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.

  DOI：

  10.1021/jp0378236