3-methoxy-4-phenoxymethylbromobenzene | 1373511-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-4-phenoxymethylbromobenzene
• 英文别名: 4-Bromo-2-methoxy-1-(phenoxymethyl)benzene
• CAS: 1373511-82-0
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: ZEVDQRSGYAQEJD-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±27.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3-methoxy-4-phenoxymethylbromobenzene 在 正丁基锂 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 7.33h， 生成 (3-methoxy-4-phenoxylmethylphenyl)carbamic acid allyl ester
  参考文献：
  名称：

  A Self-Immolative Spacer That Enables Tunable Controlled Release of Phenols under Neutral Conditions

  摘要：

  A current challenge in the area of responsive materials is the design of reagents and polymers that provide controlled release of phenols in environments that are less polar than water. In these contexts, a molecular strategy that enables release of nearly any phenol with predictable and tunable rates and without complication from background hydrolysis would substantially increase the precision with which materials can be designed to respond to a particular signal. This Article addresses this problem at the fundamental level by describing the design, synthesis, and physical-organic characterization of two small molecule self-immolative spacers that are capable of releasing phenols in organic and mixed organic aqueous solutions. The rate of release from these small molecule model systems is predictable and tunable, such that nearly any type of phenol, regardless of pK(a) value, can be released in neutral solutions without complications from nonspecific background release due to hydrolysis. Furthermore, the release properties of the spacers can be predicted from bond length and conformation data (obtained from crystal structures). On the basis of these results, it should now be possible to incorporate these design elements into materials to enable precise response properties in environments that are not 100% aqueous.

  DOI：

  10.1021/jo300400q
• 作为产物：
  描述：

  4-溴-2-甲氧基苯甲醇 、 苯酚 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 2.17h， 以49%的产率得到3-methoxy-4-phenoxymethylbromobenzene
  参考文献：
  名称：

  A Self-Immolative Spacer That Enables Tunable Controlled Release of Phenols under Neutral Conditions

  摘要：

  A current challenge in the area of responsive materials is the design of reagents and polymers that provide controlled release of phenols in environments that are less polar than water. In these contexts, a molecular strategy that enables release of nearly any phenol with predictable and tunable rates and without complication from background hydrolysis would substantially increase the precision with which materials can be designed to respond to a particular signal. This Article addresses this problem at the fundamental level by describing the design, synthesis, and physical-organic characterization of two small molecule self-immolative spacers that are capable of releasing phenols in organic and mixed organic aqueous solutions. The rate of release from these small molecule model systems is predictable and tunable, such that nearly any type of phenol, regardless of pK(a) value, can be released in neutral solutions without complications from nonspecific background release due to hydrolysis. Furthermore, the release properties of the spacers can be predicted from bond length and conformation data (obtained from crystal structures). On the basis of these results, it should now be possible to incorporate these design elements into materials to enable precise response properties in environments that are not 100% aqueous.

  DOI：

  10.1021/jo300400q