2-(3,5-difluorophenyl)-2-hydroxy-1-phenylethanone | 607391-74-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(3,5-difluorophenyl)-2-hydroxy-1-phenylethanone
• 英文别名: 3',5'-Difluorobenzoin
• CAS: 607391-74-2
• 化学式: C₁₄H₁₀F₂O₂
• 分子量: 248.229
• InChiKey: HVOMFRZRGBVXFL-UHFFFAOYSA-N

物化性质

• 沸点：
  353.7±37.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-difluorophenyl)-2-hydroxy-1-phenylethanone 在 硝酸铵 、 copper diacetate 、 溶剂黄146 作用下， 反应 2.5h， 以100%的产率得到1-(3,5-difluorophenyl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  [EN] HYDANTOINS THAT MODULATE BACE-MEDIATED APP PROCESSING
  [FR] HYDANTOÏNE MODULANT LE TRAITEMENT D'APP MÉDIÉ PAR BACE

  摘要：

  在某些实施例中，本文提供了一些有效抑制BACE对APP活性的咪唑烷酮化合物。在没有受限于特定理论的情况下，据信此处识别的咪唑烷酮的活性似乎与结合到BACE和/或APP有关，特别是当这些基团形成BACE/APP复合物时。因此，据信本文描述的化合物代表了一类新的化合物，被称为APP结合BACE抑制剂（ABBIs），并提供了一种新的机制来调节APP的加工。这里描述的咪唑烷酮似乎显示出改善的脑透过性和功能性BACE抑制作用。

  公开号：

  WO2014127042A1
• 作为产物：
  描述：

  2-苯基-1,3-二噻烷 在 正丁基锂 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 2-(3,5-difluorophenyl)-2-hydroxy-1-phenylethanone
  参考文献：
  名称：

  [EN] HYDANTOINS THAT MODULATE BACE-MEDIATED APP PROCESSING
  [FR] HYDANTOÏNE MODULANT LE TRAITEMENT D'APP MÉDIÉ PAR BACE

  摘要：

  在某些实施例中，本文提供了一些有效抑制BACE对APP活性的咪唑烷酮化合物。在没有受限于特定理论的情况下，据信此处识别的咪唑烷酮的活性似乎与结合到BACE和/或APP有关，特别是当这些基团形成BACE/APP复合物时。因此，据信本文描述的化合物代表了一类新的化合物，被称为APP结合BACE抑制剂（ABBIs），并提供了一种新的机制来调节APP的加工。这里描述的咪唑烷酮似乎显示出改善的脑透过性和功能性BACE抑制作用。

  公开号：

  WO2014127042A1

文献信息

• HYDANTOINS THAT MODULATE BACE-MEDIATED APP PROCESSING
  申请人：Buck Institute for Research on Aging

  公开号：US20140371283A1

  公开（公告）日：2014-12-18

  In certain embodiments hydantoin compounds are provided herein that are effective to inhibit BACE activity against APP. Without being bound to a particular theory, it is believed the activity of the hydantoins identified herein appears to be associated with binding to BACE and/or to APP particularly when these moieties form a BACE/APP complex. Accordingly, it is believed the compounds described herein represent a new class of compounds designated herein as APP-Binding-BACE Inhibitors (ABBIs) and provide a new mechanism to modulate APP processing. The hydantoins described herein appear to show improved brain permeability and functional BACE inhibition.

  本文提供了某些咪唑二酮化合物，其有效抑制BACE对APP的活性。虽然没有受到特定理论的约束，但人们认为，在这里识别的咪唑二酮的活性似乎与其与BACE和/或APP结合有关，尤其是当这些基团形成BACE/APP复合物时。因此，认为本文所描述的化合物代表了一类新的化合物，被称为APP结合BACE抑制剂（ABBIs），并提供了一种调节APP加工的新机制。本文所描述的咪唑二酮似乎表现出改善的脑渗透性和功能性BACE抑制作用。
• Hydantoins that modulate bace-mediated app processing
  申请人：Buck Institute for Research on Aging

  公开号：US10202355B2

  公开（公告）日：2019-02-12

  In certain embodiments hydantoin compounds are provided herein that are effective to inhibit BACE activity against APP. Without being bound to a particular theory, it is believed the activity of the hydantoins identified herein appears to be associated with binding to BACE and/or to APP particularly when these moieties form a BACE/APP complex. Accordingly, it is believed the compounds described herein represent a new class of compounds designated herein as APP-Binding-BACE Inhibitors (ABBIs) and provide a new mechanism to modulate APP processing. The hydantoins described herein appear to show improved brain permeability and functional BACE inhibition.

  在某些实施方案中，本文提供的海因化合物可有效抑制 BACE 对 APP 的活性。在不拘泥于特定理论的前提下，我们认为本文所确定的海因的活性似乎与 BACE 和/或 APP 的结合有关，特别是当这些分子形成 BACE/APP 复合物时。因此，我们认为本文所述的化合物代表了一类新的化合物，本文将其命名为 APP 结合-BACE 抑制剂 (ABBI)，并提供了一种调节 APP 处理过程的新机制。本文所述的 hydantoins 似乎具有更好的脑渗透性和功能性 BACE 抑制作用。
• Hydantoins that modulate BACE-mediated APP processing
  申请人：Buck Institute for Research on Aging

  公开号：US10766867B2

  公开（公告）日：2020-09-08

  In certain embodiments hydantoin compounds are provided herein that are effective to inhibit BACE activity against APP. Without being bound to a particular theory, it is believed the activity of the hydantoins identified herein appears to be associated with binding to BACE and/or to APP particularly when these moieties form a BACE/APP complex. Accordingly, it is believed the compounds described herein represent a new class of compounds designated herein as APP-Binding-BACE Inhibitors (ABBIs) and provide a new mechanism to modulate APP processing. The hydantoins described herein appear to show improved brain permeability and functional BACE inhibition.

  在某些实施方案中，本文提供的海因化合物可有效抑制 BACE 对 APP 的活性。在不拘泥于特定理论的前提下，我们认为本文所确定的海因的活性似乎与 BACE 和/或 APP 的结合有关，特别是当这些分子形成 BACE/APP 复合物时。因此，我们认为本文所述的化合物代表了一类新的化合物，本文将其命名为 APP 结合-BACE 抑制剂 (ABBI)，并提供了一种调节 APP 处理过程的新机制。本文所述的 hydantoins 似乎具有更好的脑渗透性和功能性 BACE 抑制作用。
• Hydantoins that modulate BACE-mediated app processing
  申请人：BUCK INSTITUTE FOR RESEARCH ON AGING

  公开号：US11091444B2

  公开（公告）日：2021-08-17

  In certain embodiments hydantoin compounds are provided herein that are effective to inhibit BACE activity against APP. Without being bound to a particular theory, it is believed the activity of the hydantoins identified herein appears to be associated with binding to BACE and/or to APP particularly when these moieties form a BACE/APP complex. Accordingly, it is believed the compounds described herein represent a new class of compounds designated herein as APP-Binding-BACE Inhibitors (ABBIs) and provide a new mechanism to modulate APP processing. The hydantoins described herein appear to show improved brain permeability and functional BACE inhibition.

  在某些实施方案中，本文提供的海因化合物可有效抑制 BACE 对 APP 的活性。在不拘泥于特定理论的前提下，我们认为本文所确定的海因的活性似乎与 BACE 和/或 APP 的结合有关，特别是当这些分子形成 BACE/APP 复合物时。因此，我们认为本文所述的化合物代表了一类新的化合物，本文将其命名为 APP 结合-BACE 抑制剂 (ABBI)，并提供了一种调节 APP 处理过程的新机制。本文所述的 hydantoins 似乎具有更好的脑渗透性和功能性 BACE 抑制作用。
• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.