(Z)-(4,4′-(ethene-1,2-diylbis(oxy))bis(1,4-phenylene))dimethanol | 1307892-60-9

• 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: (Z)-(4,4′-(ethene-1,2-diylbis(oxy))bis(1,4-phenylene))dimethanol
• CAS: 1307892-60-9
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: PGRPWDQPTQDPCD-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-(4,4′-(ethene-1,2-diylbis(oxy))bis(1,4-phenylene))dimethanol 在 食用色素红色105号 、 氧气 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 以75%的产率得到3,4-bis(4-hydroxmethylphenoxy)-1,2-dioxetane
  参考文献：
  名称：

  与二氧化硅载体结合的敏化剂药物的自催化辅助光释放

  摘要：

  敏化剂从氟化二氧化硅表面的光释放是通过单线态氧与乙烯基醚键接头的反应以及二氧杂环丁烷中间体的断裂而发生的。对释放的敏化剂进行辐照会产生单线态氧，从而通过自催化反应加速更多敏化剂的释放。正丁醇和正辛醇中敏化剂释放的 Sigmoidal 行为发生在 20 °C 的最佳温度下。由于长寿命的二氧杂环丁烷和低效的断裂，光致剥离效率在低温下降低，其中敏化剂保留在表面上，并且在高温下也降低，因为1 O 2 的反应较慢与乙烯基醚键。立即加速是释放的敏化剂被用作掺杂剂以消除诱导步骤的结果，进一步暗示了自催化机制。然而，S形敏化剂的释放与溶剂粘度、热量或二氧杂环丁烷分解产生的光或氟化二氧化硅引起的O 2溶解度的轻微增强无关。此处收集的机理信息可用于帮助控制药物释放的速度；然而，基于自催化的药物递送系统是否比具有非 S 形动力学的药物递送系统具有优势还有待观察。

  DOI：

  10.1021/jo401266r
• 作为产物：
  描述：

  meso-1,2-dibromo-1,2-bis(4-bromophenoxy)ethane 在 甲醇 、 sodium tetrahydroborate 、 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 20.33h， 生成 (Z)-(4,4′-(ethene-1,2-diylbis(oxy))bis(1,4-phenylene))dimethanol
  参考文献：
  名称：

  Photosensitizer Drug Delivery via an Optical Fiber

  摘要：

  An optical fiber has been developed with a maneuverable miniprobe tip that sparges O-2 gas and photodetaches pheophorbide (sensitizer) molecules. Singlet oxygen is produced at the probe tip surface which reacts with an alkene spacer group releasing sensitizer upon fragmentation of a dioxetane intermediate. Optimal sensitizer photorelease occurred when the probe tip was loaded with 60 nmol sensitizer, where crowding of the pheophorbide molecules and self-quenching were kept to a minimum. The fiber optic tip delivered pheophorbide molecules and singlet oxygen to discrete locations. The 60 nmol sensitizer was delivered into petrolatum; however, sensitizer release was less efficient in toluene-d(8) (3.6 nmol) where most had remained adsorbed on the probe tip, even after the covalent alkene spacer bond had been broken. The results open the door to a new area of fiber optic-guided sensitizer delivery for the potential photodynamic therapy of hypoxic structures requiring cytotoxic control.

  DOI：

  10.1021/ja200840p

文献信息

• S,S-Chiral Linker Induced U Shape with a Syn-facial Sensitizer and Photocleavable Ethene Group
  作者：Goutam Ghosh、Sarah J. Belh、Callistus Chiemezie、Niluksha Walalawela、Ashwini A. Ghogare、Mariana Vignoni、Andrés H. Thomas、Sherri A. McFarland、Edyta M. Greer、Alexander Greer

  DOI：10.1111/php.13000

  日期：2019.1

  AbstractThere is a major need for light‐activated materials for the release of sensitizers and drugs. Considering the success of chiral columns for the separation of enantiomer drugs, we synthesized an S,S‐chiral linker system covalently attached to silica with a sensitizer ethene near the silica surface. First, the silica surface was modified to be aromatic rich, by replacing 70% of the surface groups with (3‐phenoxypropyl)silane. We then synthesized a 3‐component conjugate [chlorin sensitizer, S,S‐chiral cyclohexane and ethene building blocks] in 5 steps with a 13% yield, and covalently bound the conjugate to the (3‐phenoxypropyl)silane‐coated silica surface. We hypothesized that the chiral linker would increase exposure of the ethene site for enhanced 1O2‐based sensitizer release. However, the chiral linker caused the sensitizer conjugate to adopt a U shape due to favored 1,2‐diaxial substituent orientation; resulting in a reduced efficiency of surface loading. Further accentuating the U shape was π–π stacking between the (3‐phenoxypropyl)silane and sensitizer. Semiempirical calculations and singlet oxygen luminescence data provided deeper insight into the sensitizer's orientation and release. This study has lead to insight on modifications of surfaces for drug photorelease and can help lead to the development of miniaturized photodynamic devices.