(4-methoxyphenoxymethyl)-(4-fluorophenyl)-ketone | 248256-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-methoxyphenoxymethyl)-(4-fluorophenyl)-ketone
• 英文别名: 1-(4-Fluorophenyl)-2-(4-methoxyphenoxy)ethanone
• CAS: 248256-02-2
• 化学式: C₁₅H₁₃FO₃
• mdl: MFCD03361480
• 分子量: 260.265
• InChiKey: CGKZZHLBZSHRBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenoxymethyl)-(4-fluorophenyl)-ketone 在 氢溴酸 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 3-(4-fluorophenyl)benzofuran-5-ol
  参考文献：
  名称：

  Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

  摘要：

  Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1) participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5) and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29) as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

  DOI：

  10.1016/j.bmc.2019.04.028
• 作为产物：
  描述：

  4-氟苯乙酮 在 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL 、 polymer-supported pyridinium bromide perbromide 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 (4-methoxyphenoxymethyl)-(4-fluorophenyl)-ketone
  参考文献：
  名称：

  使用聚合物支持的试剂三步合成一系列取代的苯并呋喃

  摘要：

  通过用聚合物负载的溴化吡啶鎓过溴化物（PSPBP）将苯乙酮溴化为α-溴苯乙酮，可以实现一种有效的组合方法，以取代3-苯基苯并呋喃。随后使用1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD-P）将所得的溴化物彻底替换为苯酚，并使用Amberlyst 15将所得的α-苯氧基乙酰苯酮环化脱水，得到的纯产品不含需要任何色谱纯化步骤。

  DOI：

  10.1039/a904384e

文献信息

• Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and S_NAr Chemistry
  作者：Kurt Polidano、Benjamin G. Reed-Berendt、Anaïs Basset、Andrew J. A. Watson、Jonathan M. J. Williams、Louis C. Morrill

  DOI：10.1021/acs.orglett.7b03441

  日期：2017.12.15

  A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice

  报道了一种通过电子芳烃活化对苯甲醇进行催化官能化的氢转移策略，该方法以优异的分离产率获得了各种定制的二芳基醚和芳基胺（38例，平均产率为70％）。利用氢转移方法，可以通过明智地选择简单和廉价的添加剂来选择功能化产物的氧化水平。
• Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels–Alder reaction: Synthesis and cytotoxicity evaluation
  作者：Yu-Dong Shen、Yuan-Xin Tian、Xian-Zhang Bu、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2009.04.016

  日期：2009.10

  oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation–cycloaddition–aromatization procedure. The regiospecific Diels–Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization

  通过IBX氧化-环加成-芳构化方法，从容易获得的苯并呋喃醇和N-取代的二烯中合成了一系列新的天然丹参酮样氧杂环稠合的邻醌衍生物。N-二烯的区域特异性Diels–Alder环加成反应可通过多种亲双烯体有效实现。发现通过控制芳构化条件可以保留或消除分子中的酰胺部分。选定的氧杂环稠合的邻醌以及几种硫杂环稠合的邻醌我们评估了之前获得的对苯二酚对不同癌细胞系的细胞毒性，并讨论了结构-活性关系（SAR）。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• Tribenzoyl compounds
  申请人：Chevron Phillips Chemical Company LP

  公开号：US20030062505A1

  公开（公告）日：2003-04-03

  An oxygen scavenging composition or system is provided comprising an oxygen scavenging material, a photoinitiator, and at least one catalyst effective in catalyzing an oxygen scavenging reaction, wherein the photoinitiator comprises a benzophenone derivative containing at least two benzophenone moieties. A film, a multi-phase composition, a multi-layer composition, a multi-layer film, an article comprising the oxygen scavenging composition, a method for preparing the oxygen scavenging composition, and a method for scavenging oxygen are also provided. Non-extractable benzophenone derivative photoinitiators and methods for preparing same are also provided.

  提供了一种氧气清除组合物或系统，包括一个氧气清除材料、一个光引发剂和至少一个催化剂，有效地催化氧气清除反应，其中光引发剂包括至少两个苯并苯酮基团的苯并苯酮衍生物。还提供了一种薄膜、多相组合物、多层组合物、多层薄膜、包括氧气清除组合物的物品，制备氧气清除组合物的方法以及清除氧气的方法。还提供了不可提取的苯并苯酮衍生物光引发剂及其制备方法。
• Electrochemical Dearomative Amination of Phenol Derivatives: Access to Spirooxazolidinones
  作者：Jin-Lin Wan、Jing-Mei Huang

  DOI：10.1002/adsc.202300118

  日期：——

  An electrochemical oxidative approach to spirooxazolidinones from phenol derivatives via intramolecular dearomative amination reactions is developed. This reaction proceeds without metal catalysts and external chemical oxidants, and shows broad substrate scope and diverse functional group compatibility. The synthetic utility of this strategy is further exhibited by the gram-scale synthesis and late-stage

  开发了一种通过分子内脱芳胺化反应从苯酚衍生物中制备螺恶唑烷酮的电化学氧化方法。该反应在没有金属催化剂和外部化学氧化剂的情况下进行，并显示出广泛的底物范围和不同的官能团相容性。克级合成和后期功能化进一步展示了该策略的合成效用。通过稍微调整反应条件，可以从苯酚衍生物中得到醇（1°、2° 和 3°），这是使对甲氧基苯基 (PMP) 脱保护以恢复醇功能的良好策略。