2-[2-[2-(2-Prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl 4-(dodecanoyloxymethyl)-3-nitrobenzoate | 1355155-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-[2-(2-Prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl 4-(dodecanoyloxymethyl)-3-nitrobenzoate
• 英文别名: 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl 4-(dodecanoyloxymethyl)-3-nitrobenzoate
• CAS: 1355155-08-6
• 化学式: C₃₁H₄₇NO₁₁
• 分子量: 609.714
• InChiKey: QQMJSNMNARGNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-[2-[2-(2-Prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl 4-(dodecanoyloxymethyl)-3-nitrobenzoate 生成 13-oxo-3,6,9,12-tetraoxapentadec-14-en-1-yl 4-formyl-3-nitrosobenzoate
  参考文献：
  名称：

  Stabilized Vesicles Consisting of Small Amphiphiles for Stepwise Photorelease via UV Light

  摘要：

  A small amphiphile consisting of hydrophilic tetraethylene glycol monoacrylate and hydrophobic alkyl chain which were connected by an o-nitrobenzyl unit, a photolabile group, was designed and synthesized. The critical aggregate concentration of the synthesized amphiphile was determined to be about 3 x 10(-5) M by the fluorescence probe technique. Nanosized vesicles were prepared and stabilized by in-situ radical polymerization without altering the morphology. The polymeric vesicle was highly stable which retained vesicular shape under dilution or UV irradiation. Hydrophobic guests can be encapsulated within the vesicle membrane and released out of the vesicle by UV stimulus through splitting the amphiphilic structure of the amphiphile. Distinguished dose-controlled photorelease of the polymeric vesicle is achieved due to the maintenance of the vesicular shape integrity which makes the guest release depend on the cleavage amount of amphiphilic structure during UV irradiation. This study provides a promising strategy to develop stable drug delivery systems for sustained and phototriggered release.

  DOI：

  10.1021/la203829d
• 作为产物：
  描述：

  三缩四乙二醇 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 25.0h， 生成 2-[2-[2-(2-Prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl 4-(dodecanoyloxymethyl)-3-nitrobenzoate
  参考文献：
  名称：

  Stabilized Vesicles Consisting of Small Amphiphiles for Stepwise Photorelease via UV Light

  摘要：

  A small amphiphile consisting of hydrophilic tetraethylene glycol monoacrylate and hydrophobic alkyl chain which were connected by an o-nitrobenzyl unit, a photolabile group, was designed and synthesized. The critical aggregate concentration of the synthesized amphiphile was determined to be about 3 x 10(-5) M by the fluorescence probe technique. Nanosized vesicles were prepared and stabilized by in-situ radical polymerization without altering the morphology. The polymeric vesicle was highly stable which retained vesicular shape under dilution or UV irradiation. Hydrophobic guests can be encapsulated within the vesicle membrane and released out of the vesicle by UV stimulus through splitting the amphiphilic structure of the amphiphile. Distinguished dose-controlled photorelease of the polymeric vesicle is achieved due to the maintenance of the vesicular shape integrity which makes the guest release depend on the cleavage amount of amphiphilic structure during UV irradiation. This study provides a promising strategy to develop stable drug delivery systems for sustained and phototriggered release.

  DOI：

  10.1021/la203829d

文献信息

• Stabilized Vesicles Consisting of Small Amphiphiles for Stepwise Photorelease via UV Light
  作者：Jianming Dong、Yi Zeng、Zhiqing Xun、Yongbin Han、Jinping Chen、Ying-Ying Li、Yi Li

  DOI：10.1021/la203829d

  日期：2012.1.24

  A small amphiphile consisting of hydrophilic tetraethylene glycol monoacrylate and hydrophobic alkyl chain which were connected by an o-nitrobenzyl unit, a photolabile group, was designed and synthesized. The critical aggregate concentration of the synthesized amphiphile was determined to be about 3 x 10(-5) M by the fluorescence probe technique. Nanosized vesicles were prepared and stabilized by in-situ radical polymerization without altering the morphology. The polymeric vesicle was highly stable which retained vesicular shape under dilution or UV irradiation. Hydrophobic guests can be encapsulated within the vesicle membrane and released out of the vesicle by UV stimulus through splitting the amphiphilic structure of the amphiphile. Distinguished dose-controlled photorelease of the polymeric vesicle is achieved due to the maintenance of the vesicular shape integrity which makes the guest release depend on the cleavage amount of amphiphilic structure during UV irradiation. This study provides a promising strategy to develop stable drug delivery systems for sustained and phototriggered release.