4-(2-(benzyloxy)ethoxy)benzonitrile | 186970-30-9

• 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: 4-(2-(benzyloxy)ethoxy)benzonitrile
• 英文别名: 4-(2-Phenylmethoxyethoxy)benzonitrile
• CAS: 186970-30-9
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: WBROAYFNPGXNOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-(benzyloxy)ethoxy)benzonitrile 在 2,6-二甲基吡啶 、 盐酸 、 甲烷磺酸 、 碘代三甲硅烷 、 sodium hydride 、 苯硫酚 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 106.17h， 生成 [5-[4-(2-Methylsulfonyloxyethoxy)phenyl]-6-pyridin-2-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
• 作为产物：
  描述：

  2-苄氧基乙醇 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 72.5h， 生成 4-(2-(benzyloxy)ethoxy)benzonitrile
  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

文献信息

• Monoamine oxidase inhibition by C4-substituted phthalonitriles
  作者：Clarina I. Manley-King、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bioorg.2011.10.003

  日期：2012.2

  studies suggested that the phthalimide ring forms numerous polar interactions with the polar region of the MAO-B substrate cavity while the C5 side chain extends to, and interacts via Van der Waals interactions with the hydrophobic regions of the enzyme entrance cavity. Interactions with both cavities appear to be requirements for high affinity binding. In the present study we have examined an analogs series

  最近有报道称，一系列C5取代的邻苯二甲酰亚胺是重组人单胺氧化酶（MAO）B的强效可逆抑制剂。建模研究表明，邻苯二甲酰亚胺环与MAO-B底物腔的极性区域形成许多极性相互作用，而C5侧链延伸至范德华相互作用，并通过范德华相互作用与酶进入腔的疏水区相互作用。与两个腔体的相互作用似乎是高亲和力结合的要求。在本研究中，我们已经研究了一系列C4取代的邻苯二甲腈作为潜在的人MAO抑制剂的类似物。发现邻苯二甲腈是高度有效的可逆MAO-B抑制剂，大多数类似物的IC 50均高数值在低nM范围内。邻苯二甲腈也与人MAO-A相互作用，尽管与MAO-B相比具有较低的结合亲和力。模型研究表明，邻苯二甲腈与MAO-B的高结合亲和力可能至少部分取决于腈官能团与酶底物腔之间极性相互作用的形成。对苯甲腈同系物系列的检查确定，对于相应的苯甲腈部分，邻苯二甲腈部分对MAO-B的抑制作用最佳，而与C4取代的苯甲腈相比，C3取代的苯
• Solvent-controlled synthesis of bulky and polar-bulky galactonoamidines
  作者：Susanne Striegler、Ifedi Orizu

  DOI：10.1016/j.carres.2022.108520

  日期：2022.3

  The goal of this study was the design and synthesis of bulky and polar-bulky galactonoamidines that have a potential to interact with both catalytic amino acids in the active site of human α-galactosidase. While a library of more than 25 compounds was previously synthesized following established protocols, the coupling of the selected amines with activated perbenzylated galactothionolactam yielded

  本研究的目的是设计和合成大块和极性大的半乳糖脒，它们有可能与人 α-半乳糖苷酶活性位点中的两种催化氨基酸相互作用。虽然先前按照既定方案合成了超过 25 种化合物的库，但所选胺与活化的过苄基化半乳糖硫内酰胺的偶联对于一些过苄基化目标仅产生少量。一种计算方法揭示了选定加合物的相对能量差异，并建议改变溶剂，然后成功合成 20-75% 的前体化合物。随后尝试通过 Pd 催化氢化对过苄基化半乳糖脒进行全局脱保护，导致不需要的 Pd 配位、不完全脱苄基化反应、部分化合物水解、甚至完全分解。在修改去苄基化条件后，制定了一个冗长的协议来纯化目标碳水化合物衍生物。
• 1-Aryl-2-pyridyl-3,4-dihydronaphthalenes:  Photofluorogenic Ligands for the Estrogen Receptor
  作者：Andrew W. Scribner、Serkos A. Haroutounian、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1021/jo9618029

  日期：1997.2.1

  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.