2-ethylidene-4-hexyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-ethylidene-4-hexyl-1,3-dioxolane
• 英文别名: EHD
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: LMNRYVNJUITJDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethylidene-4-hexyl-1,3-dioxolane 、 β-环糊精 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Shell-Sheddable, pH-Sensitive Supramolecular Nanoparticles Based on Ortho Ester-Modified Cyclodextrin and Adamantyl PEG

  摘要：

  We report a new type of pH-sensitive supramolecular aggregates which possess a programmable character of sequential dePEGylation and degradation. As a platform of designing and building multifunctional supramolecular nanoparticles, a family of 6-OH ortho ester-modified beta-cyclodextrin (beta-CD) derivatives have been synthesized via the facile reaction between beta-CD and cyclic ketene acetals with different alkyl lengths. These asymmetric acid-labile beta-CD derivatives formed amphiphilic supramolecules with adamantane-modified PEG through host-guest interaction in polar solvents such as ethanol. The supramolecules can self-assemble in water to form acid-labile supramolecular aggregates. The results of TEM and light scattering measurements demonstrate that the size and morphology of the aggregates are influenced by the alkyl or PEG length and the host-guest feed ratio. By carefully balancing the alkyl and PEG lengths and adjusting the host-guest ratio, well-dispersed vesicles (50-100 nm) or sphere-like nanoparticles (200-500 nm) were obtained. Zeta potential measurements reveal that these supramolecular aggregates are capable of being surface-functionalized via dynamic host-guest interaction. The supramolecular aggregates were stable at pH 8.4 for at least 12 h as proven by the (1)H NMR and LLS measurements. However, rapid dePEGylation occurred at pH 7.4 due to the hydrolysis of the ortho ester linkages locating at the interface, which resulted in aggregation of the dePEGylated hydrophobic inner cores. Upon further decreasing the pH to 6.4, the hydrophobic cores were further degraded due to the acid-accelerated hydrolysis of the ortho esters. The incubation stability of the acid-labile supramolecular aggregates in neutral buffer could be improved by incorporating hydrophobic poly(e-caprolactone) into the core of the aggregates.

  DOI：

  10.1021/bm500711c
• 作为产物：
  描述：

  1,2-辛二醇 在 tris(triphenylphosphine)ruthenium(II) chloride 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 2-ethylidene-4-hexyl-1,3-dioxolane
  参考文献：
  名称：

  Shell-Sheddable, pH-Sensitive Supramolecular Nanoparticles Based on Ortho Ester-Modified Cyclodextrin and Adamantyl PEG

  摘要：

  We report a new type of pH-sensitive supramolecular aggregates which possess a programmable character of sequential dePEGylation and degradation. As a platform of designing and building multifunctional supramolecular nanoparticles, a family of 6-OH ortho ester-modified beta-cyclodextrin (beta-CD) derivatives have been synthesized via the facile reaction between beta-CD and cyclic ketene acetals with different alkyl lengths. These asymmetric acid-labile beta-CD derivatives formed amphiphilic supramolecules with adamantane-modified PEG through host-guest interaction in polar solvents such as ethanol. The supramolecules can self-assemble in water to form acid-labile supramolecular aggregates. The results of TEM and light scattering measurements demonstrate that the size and morphology of the aggregates are influenced by the alkyl or PEG length and the host-guest feed ratio. By carefully balancing the alkyl and PEG lengths and adjusting the host-guest ratio, well-dispersed vesicles (50-100 nm) or sphere-like nanoparticles (200-500 nm) were obtained. Zeta potential measurements reveal that these supramolecular aggregates are capable of being surface-functionalized via dynamic host-guest interaction. The supramolecular aggregates were stable at pH 8.4 for at least 12 h as proven by the (1)H NMR and LLS measurements. However, rapid dePEGylation occurred at pH 7.4 due to the hydrolysis of the ortho ester linkages locating at the interface, which resulted in aggregation of the dePEGylated hydrophobic inner cores. Upon further decreasing the pH to 6.4, the hydrophobic cores were further degraded due to the acid-accelerated hydrolysis of the ortho esters. The incubation stability of the acid-labile supramolecular aggregates in neutral buffer could be improved by incorporating hydrophobic poly(e-caprolactone) into the core of the aggregates.

  DOI：

  10.1021/bm500711c

文献信息

• Shell-Sheddable, pH-Sensitive Supramolecular Nanoparticles Based on Ortho Ester-Modified Cyclodextrin and Adamantyl PEG
  作者：Ran Ji、Jing Cheng、Ting Yang、Cheng−Cheng Song、Lei Li、Fu-Sheng Du、Zi-Chen Li

  DOI：10.1021/bm500711c

  日期：2014.10.13

  We report a new type of pH-sensitive supramolecular aggregates which possess a programmable character of sequential dePEGylation and degradation. As a platform of designing and building multifunctional supramolecular nanoparticles, a family of 6-OH ortho ester-modified beta-cyclodextrin (beta-CD) derivatives have been synthesized via the facile reaction between beta-CD and cyclic ketene acetals with different alkyl lengths. These asymmetric acid-labile beta-CD derivatives formed amphiphilic supramolecules with adamantane-modified PEG through host-guest interaction in polar solvents such as ethanol. The supramolecules can self-assemble in water to form acid-labile supramolecular aggregates. The results of TEM and light scattering measurements demonstrate that the size and morphology of the aggregates are influenced by the alkyl or PEG length and the host-guest feed ratio. By carefully balancing the alkyl and PEG lengths and adjusting the host-guest ratio, well-dispersed vesicles (50-100 nm) or sphere-like nanoparticles (200-500 nm) were obtained. Zeta potential measurements reveal that these supramolecular aggregates are capable of being surface-functionalized via dynamic host-guest interaction. The supramolecular aggregates were stable at pH 8.4 for at least 12 h as proven by the (1)H NMR and LLS measurements. However, rapid dePEGylation occurred at pH 7.4 due to the hydrolysis of the ortho ester linkages locating at the interface, which resulted in aggregation of the dePEGylated hydrophobic inner cores. Upon further decreasing the pH to 6.4, the hydrophobic cores were further degraded due to the acid-accelerated hydrolysis of the ortho esters. The incubation stability of the acid-labile supramolecular aggregates in neutral buffer could be improved by incorporating hydrophobic poly(e-caprolactone) into the core of the aggregates.