bis(12-hydroxydodecyl) disulfide | 187339-28-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: bis(12-hydroxydodecyl) disulfide
• 英文别名: 12-(12-Hydroxydodecyldisulfanyl)dodecan-1-ol；12-(12-hydroxydodecyldisulfanyl)dodecan-1-ol
• CAS: 187339-28-2
• 化学式: C₂₄H₅₀O₂S₂
• 分子量: 434.792
• InChiKey: XOALUBQUJSQWDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异烟酸 、 bis(12-hydroxydodecyl) disulfide 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 bis[12-((pyridinecarbonyl)oxy)dodecyl] disulfide
  参考文献：
  名称：

  细胞色素血红素单元与电极的直接连接：电化学研究

  摘要：

  展示了一种将细胞色素 c 固定在化学修饰电极表面的新策略，并用于研究蛋白质的电子转移动力学。链烷硫醇和欧米茄封端的链烷硫醇（以吡啶、咪唑或能够与血红素结合的腈基团封端）的混合单层膜用于将细胞色素 c 吸附到金电极的表面。与纯薄膜相比，使用混合薄膜可以使吸附的细胞色素的浓度保持稀释，并确保其环境具有更高程度的均匀性。使用电化学方法和扫描隧道显微镜研究吸附的蛋白质。

  DOI：

  10.1021/ja025518c
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 sodium hydroxide 、 碘 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 1.33h， 生成 bis(12-hydroxydodecyl) disulfide
  参考文献：
  名称：

  Quantum Interference Effects in Self-Assembled Asymmetric Disulfide Monolayers:  Comparisons between Experiment and ab Initio/Monte Carlo Theories

  摘要：

  Electron transfer measurements between solution redox probes and a Au electrode coated with self-assembled monolayers of symmetric and asymmetric omega-hydroxyalkane disulfides are used to probe the quantum interference between hydrocarbon chains of different lengths, While nb initio theory predicts a measurable destructive interference effect between hydrocarbon chains differing in length by a single methylene unit, electron transfer rates for the ferricyanide and horse heart cytochrome c are more consistent with rates estimated in the absence of the interference effect. The discrepancy between theory and experiment is discussed in light of possible interchain electronic coupling and phase segregation within the monolayers and limitations of the theoretical models.

  DOI：

  10.1021/jp962731k

文献信息

• Direct Wiring of Cytochrome <i>c</i>'s Heme Unit to an Electrode:  Electrochemical Studies
  作者：Jianjun Wei、Haiying Liu、Allison R. Dick、Hiromichi Yamamoto、Yufan He、David H. Waldeck

  DOI：10.1021/ja025518c

  日期：2002.8.1

  of cytochrome c on the surface of chemically modified electrodes is demonstrated and used to investigate the protein's electron-transfer kinetics. Mixed monolayer films of alkanethiols and omega-terminated alkanethiols (terminated with pyridine, imidazole, or nitrile groups that are able to ligate with the heme) are used to adsorb cytochrome c to the surface of gold electrodes. The use of mixed films

  展示了一种将细胞色素 c 固定在化学修饰电极表面的新策略，并用于研究蛋白质的电子转移动力学。链烷硫醇和欧米茄封端的链烷硫醇（以吡啶、咪唑或能够与血红素结合的腈基团封端）的混合单层膜用于将细胞色素 c 吸附到金电极的表面。与纯薄膜相比，使用混合薄膜可以使吸附的细胞色素的浓度保持稀释，并确保其环境具有更高程度的均匀性。使用电化学方法和扫描隧道显微镜研究吸附的蛋白质。
• Quantum Interference Effects in Self-Assembled Asymmetric Disulfide Monolayers:  Comparisons between Experiment and <i>ab Initio</i>/Monte Carlo Theories
  作者：Jun Cheng、Cary J. Miller

  DOI：10.1021/jp962731k

  日期：1997.2.1

  Electron transfer measurements between solution redox probes and a Au electrode coated with self-assembled monolayers of symmetric and asymmetric omega-hydroxyalkane disulfides are used to probe the quantum interference between hydrocarbon chains of different lengths, While nb initio theory predicts a measurable destructive interference effect between hydrocarbon chains differing in length by a single methylene unit, electron transfer rates for the ferricyanide and horse heart cytochrome c are more consistent with rates estimated in the absence of the interference effect. The discrepancy between theory and experiment is discussed in light of possible interchain electronic coupling and phase segregation within the monolayers and limitations of the theoretical models.