2-(benzyloxy)-2,5-dihydrofuran | 212270-74-1

• 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: 2-(benzyloxy)-2,5-dihydrofuran
• 英文别名: 2-Phenylmethoxy-2,5-dihydrofuran
• CAS: 212270-74-1
• 化学式: C₁₁H₁₂O₂
• mdl: MFCD09033575
• 分子量: 176.215
• InChiKey: VOQNTNBPPNLFJF-UHFFFAOYSA-N

物化性质

• 沸点：
  272.4±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 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：

  2-(benzyloxy)-2,5-dihydrofuran 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以75%的产率得到benzyl β-D-erythroside
  参考文献：
  名称：

  Development of Noviomimetics as C-Terminal Hsp90 Inhibitors

  摘要：

  KU-32 and KU-596 are novobiocin-derived, C terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.

  DOI：

  10.1021/acsmedchemlett.5b00331
• 作为产物：
  描述：

  trans-2-(benzyloxy)-3-(phenylselenyl)tetrahydrofuran 在 吡啶 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到2-(benzyloxy)-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis and Ring-Opening Reactions of the Diastereoisomericcis- andtrans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199808)1998:8<1675::aid-ejoc1675>3.0.co;2-b

文献信息

• Synthesis of Mono- and Dihydroxylated Furanoses, Pyranoses, and an Oxepanose for the Preparation of Natural Product Analogue Libraries
  作者：Xiao Ming Yu、Huijong Han、Brian S. J. Blagg

  DOI：10.1021/jo050558v

  日期：2005.7.1

  Numerous biologically active natural products contain furanoses and pyranoses with mono- and dihydroxylated substituents. However, much of the structure−activity studies on such molecules is gathered on the aglycons without attention to the corresponding carbohydrate components. Consequently, there are few synthetic procedures that enable the rapid preparation of mono- and dihydroxyfuranoses and mono-

  许多具有生物活性的天然产物都含有呋喃糖酶和带有单羟基和二羟基取代基的吡喃糖酶。但是，对此类分子的许多结构活性研究都是在糖苷配基上进行的，而没有关注相应的碳水化合物成分。因此，几乎没有能够快速制备单和二羟基呋喃糖酶和单和二羟基吡喃糖的合成方法，也没有关于3，4-二羟基氧戊糖的报道。在本文中，我们报告了正交保护的五元，六元和七元碳水化合物衍生物的实用合成。合成这些分子的简洁方式允许快速制备类似物，旨在发现吡喃糖骨架上的环大小和单个羟基部分的作用。
• Development of Noviomimetics as C-Terminal Hsp90 Inhibitors
  作者：Mercy Anyika、Mason McMullen、Leah K. Forsberg、Rick T. Dobrowsky、Brian S. J. Blagg

  DOI：10.1021/acsmedchemlett.5b00331

  日期：2016.1.14

  KU-32 and KU-596 are novobiocin-derived, C terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.
• Synthesis and Ring-Opening Reactions of the Diastereoisomericcis- andtrans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1002/(sici)1099-0690(199808)1998:8<1675::aid-ejoc1675>3.0.co;2-b

  日期：1998.8