1,3-二噁戊环,2-亚乙基-4-甲基- | 182550-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 中文名称: 1,3-二噁戊环,2-亚乙基-4-甲基-
• 英文名称: 2-ethylidene-4-methyl-1,3-dioxolane
• 英文别名: EMD
• CAS: 182550-87-4
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: DLVBGWQRCHNXFU-UHFFFAOYSA-N

物化性质

• 沸点：
  159.9±20.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,3-二噁戊环,2-亚乙基-4-甲基- 、 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， 以80%的产率得到
  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：

  2-乙烯基-4-甲基-1,3-二氧戊环 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 1,3-二噁戊环,2-亚乙基-4-甲基-
  参考文献：
  名称：

  用侧基侧酯容易合成酸不稳定的聚合物

  摘要：

  这项工作提出了一种简便的方法，用于制备带有侧链环酯的酸不稳定和生物相容性聚合物，该方法基于环状烯酮缩醛（CKA）与羟基之间的有效且温和的反应。分别从CKA制备了三个CKA，2-亚乙基-1,3-二氧戊环（EDO），2-亚乙基-1,3-二氧戊环（EDL）和2-亚乙基-4-甲基-1,3-二氧戊环（EMD）。通过双键的催化异构化得到相应的环状乙烯基缩醛。使用痕量对甲苯磺酸作为催化剂，检查了CKA与不同醇和二醇的反应。对于一羟基醇，通过与乙醇简单地向CKA加成羟基，即可形成环状原酸酯，与异氰酸酯相比，其反应活性要大得多。-丙醇。当使用1,2-或1,3-二醇与CKA反应时，除了简单的加成产物外，我们还观察到了异构化的环状原酸酯。然后用CKA改性生物相容性多元醇，即聚丙烯酸2-羟乙酯（PHEA）和聚乙烯醇（PVA），并且可以通过改变进料比轻松调节侧链原酸酯的取代度。小分子原酸酯和经CKA改性的聚合物均显

  DOI：

  10.1021/bm201410c

文献信息

• Krompiec; Maslinska-Solich; Suwinski, Polish Journal of Chemistry, 1996, vol. 70, # 8, p. 1087 - 1090
  作者：Krompiec、Maslinska-Solich、Suwinski、Macionga

  DOI：——

  日期：——
• 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.
• Facile Synthesis of Acid-Labile Polymers with Pendent Ortho Esters
  作者：Jing Cheng、Ran Ji、Shi-Juan Gao、Fu-Sheng Du、Zi-Chen Li

  DOI：10.1021/bm201410c

  日期：2012.1.9

  p-toluenesulfonic acid as a catalyst. For the monohydroxyl alcohols, cyclic ortho esters were formed by simple addition of the hydroxyl group toward CKAs with ethanol showing a much greater reactivity than iso-propanol. When 1,2- or 1,3-diols were used to react with the CKAs, we observed the isomerized cyclic ortho esters besides the simple addition products. Biocompatible polyols, that is, poly(2-hydroxyethyl

  这项工作提出了一种简便的方法，用于制备带有侧链环酯的酸不稳定和生物相容性聚合物，该方法基于环状烯酮缩醛（CKA）与羟基之间的有效且温和的反应。分别从CKA制备了三个CKA，2-亚乙基-1,3-二氧戊环（EDO），2-亚乙基-1,3-二氧戊环（EDL）和2-亚乙基-4-甲基-1,3-二氧戊环（EMD）。通过双键的催化异构化得到相应的环状乙烯基缩醛。使用痕量对甲苯磺酸作为催化剂，检查了CKA与不同醇和二醇的反应。对于一羟基醇，通过与乙醇简单地向CKA加成羟基，即可形成环状原酸酯，与异氰酸酯相比，其反应活性要大得多。-丙醇。当使用1,2-或1,3-二醇与CKA反应时，除了简单的加成产物外，我们还观察到了异构化的环状原酸酯。然后用CKA改性生物相容性多元醇，即聚丙烯酸2-羟乙酯（PHEA）和聚乙烯醇（PVA），并且可以通过改变进料比轻松调节侧链原酸酯的取代度。小分子原酸酯和经CKA改性的聚合物均显