[5-[4-[2-(Aziridin-1-yl)ethoxy]phenyl]-6-pyridin-3-yl-7,8-dihydronaphthalen-2-yl] trifluoromethanesulfonate | 186970-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [5-[4-[2-(Aziridin-1-yl)ethoxy]phenyl]-6-pyridin-3-yl-7,8-dihydronaphthalen-2-yl] trifluoromethanesulfonate
• CAS: 186970-81-0
• 化学式: C₂₆H₂₃F₃N₂O₄S
• 分子量: 516.541
• InChiKey: KCEATWNUJKUHJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [5-[4-[2-(Aziridin-1-yl)ethoxy]phenyl]-6-pyridin-3-yl-7,8-dihydronaphthalen-2-yl] trifluoromethanesulfonate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到1-[4-(2-aziridinylethoxy)phenyl]-6-hydroxy-2-(3-pyridyl)-3,4-dihydronaphthalene
  参考文献：
  名称：

  1-Aryl-2-pyridyl-3,4-dihydronaphthalenes:  Photofluorogenic Ligands for the Estrogen Receptor

  摘要：

  Three 1,2-substituted-3,4-dihydronaphthalenes that are pyridine analogs of the antiestrogen desmethylnafoxidine were prepared and evaluated as fluorescent ligands for the estrogen receptor. These compounds represent a class of fluorescent probes that we term ''photofluorogenic'', denoting their ability to exist initially as a high affinity though weakly fluorescent stilbazole form which can be photocyclized-oxidized to a highly fluorescent though low affinity azaphenanthrenoid form. These probes also contain an aziridine function that provides a means for their permanent, covalent attachment to the receptor. The three dihydronaphthalene systems were prepared by efficient routes from alpha-(2-, 3-, and 4-pyridyl)acetophenone precursors. They demonstrate high apparent affinity for the estrogen receptor and show time-dependent irreversible inactivation, consistent with their covalent attachment to the receptor via the aziridine function. Each system is converted into an azaphenanthrene by photocyclization-oxidation of the cis-stilbazole unit. The absorbance and fluorescence emission spectra of the dihydronaphthalene precursors and azaphenanthrene products have been characterized, and they display marked sensitivity to both solvent polarity and pH. The azaphenanthrenoids derived from the 2- and 4-pyridyl isomers exhibit intense emission at wavelengths that exceed 500 nn under certain conditions and appear to be well suited as fluorescent probes for the estrogen receptor.

  DOI：

  10.1021/jo9618029
• 作为产物：
  描述：

  1-[4-(2-Phenylmethoxyethoxy)phenyl]-2-pyridin-3-ylethanol 在 2,6-二甲基吡啶 、 jones reagent 、 甲烷磺酸 、 碘代三甲硅烷 、 sodium hydride 、 苯硫酚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 126.25h， 生成 [5-[4-[2-(Aziridin-1-yl)ethoxy]phenyl]-6-pyridin-3-yl-7,8-dihydronaphthalen-2-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  1-Aryl-2-pyridyl-3,4-dihydronaphthalenes:  Photofluorogenic Ligands for the Estrogen Receptor

  摘要：

  Three 1,2-substituted-3,4-dihydronaphthalenes that are pyridine analogs of the antiestrogen desmethylnafoxidine were prepared and evaluated as fluorescent ligands for the estrogen receptor. These compounds represent a class of fluorescent probes that we term ''photofluorogenic'', denoting their ability to exist initially as a high affinity though weakly fluorescent stilbazole form which can be photocyclized-oxidized to a highly fluorescent though low affinity azaphenanthrenoid form. These probes also contain an aziridine function that provides a means for their permanent, covalent attachment to the receptor. The three dihydronaphthalene systems were prepared by efficient routes from alpha-(2-, 3-, and 4-pyridyl)acetophenone precursors. They demonstrate high apparent affinity for the estrogen receptor and show time-dependent irreversible inactivation, consistent with their covalent attachment to the receptor via the aziridine function. Each system is converted into an azaphenanthrene by photocyclization-oxidation of the cis-stilbazole unit. The absorbance and fluorescence emission spectra of the dihydronaphthalene precursors and azaphenanthrene products have been characterized, and they display marked sensitivity to both solvent polarity and pH. The azaphenanthrenoids derived from the 2- and 4-pyridyl isomers exhibit intense emission at wavelengths that exceed 500 nn under certain conditions and appear to be well suited as fluorescent probes for the estrogen receptor.

  DOI：

  10.1021/jo9618029