cis-1,2-bis(4-bromophenoxy)ethene | 255709-15-0

• 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: cis-1,2-bis(4-bromophenoxy)ethene
• 英文别名: 1-bromo-4-[(Z)-2-(4-bromophenoxy)ethenoxy]benzene
• CAS: 255709-15-0
• 化学式: C₁₄H₁₀Br₂O₂
• 分子量: 370.04
• InChiKey: MNUADKRHLDMWJC-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  cis-1,2-bis(4-bromophenoxy)ethene 在 正丁基锂 、 水 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.33h， 以95%的产率得到1,2-cis-diphenoxyethylene
  参考文献：
  名称：

  Synthesis of cis- and trans-1,2-Diphenoxyethenes and p,p‘-Disubstituted Diaryloxyethenes

  摘要：

  DOI：

  10.1021/jo9812577
• 作为产物：
  描述：

  1,2-双(4-溴苯氧基)乙烷 在 N-溴代丁二酰亚胺(NBS) 、 sodium iodide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 8.0h， 生成 cis-1,2-bis(4-bromophenoxy)ethene
  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

• Intramolecular site selectivity in cation radical Diels-Alder cycloadditions of difunctional and trifunctional dienophiles
  作者：Nathan L. Bauld、Jingkui Yang

  DOI：10.1002/1099-1395(200009)13:9<518::aid-poc288>3.0.co;2-9

  日期：2000.9

  moieties are included, two of them being of the styrene type and one of the 1,2-diaryloxyethene type, the reaction is again specific for the styrene moieties, giving only the bis-adduct. The high site selectivity observed in these reactions is especially noteworthy in view of the observation that monofunctional molecules containing all three of these moieties are found to be reactive toward Diels–Alder

  测定了在三（4-溴苯基）六氯锑酸铵催化下，几种双官能团和三官能团亲双烯体与 1,3-环戊二烯的阳离子自由基 Diels-Alder 反应。当两个反应位点都是 4-甲氧基苯乙烯类型时，反应在两个苯乙烯部分顺利发生，得到双加合物。然而，当一个反应性部分是苯乙烯类而一个是烯醇醚类时，即使在大量过量的环戊二烯存在下，反应也仅在苯乙烯部分发生以产生单加合物。当包括三个潜在的反应性部分时，其中两个是苯乙烯类型，一个是 1,2-二芳氧基乙烯类型，该反应再次对苯乙烯部分具有特异性，仅产生双加合物。在这些反应中观察到的高位点选择性特别值得注意，因为观察到包含所有这三个部分的单官能分子被发现在相同的反应条件下对 Diels-Alder 加合物的形成具有反应性，并且这些加合物在反应条件。版权所有 © 2000 John Wiley & Sons, Ltd.
• Synthesis of <i>cis</i>- and <i>trans</i>-1,2-Diphenoxyethenes and <i>p</i>,<i>p‘</i>-Disubstituted Diaryloxyethenes
  作者：Jingkui Yang、Nathan L. Bauld

  DOI：10.1021/jo9812577

  日期：1999.12.1
• Photosensitizer Drug Delivery via an Optical Fiber
  作者：Matibur Zamadar、Goutam Ghosh、Adaickapillai Mahendran、Mihaela Minnis、Bonnie I. Kruft、Ashwini Ghogare、David Aebisher、Alexander Greer

  DOI：10.1021/ja200840p

  日期：2011.5.25

  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.