5-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyloxy-5H-furan-2-one | 738604-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyloxy-5H-furan-2-one
• 英文别名: 5-[(3-(t-butyldiphenylsilyloxy)propyl)]-5-methoxy-5H-furan-2-one；5-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-5-methoxy-5H-furan-2-one；5-[3-[Tert-butyl(diphenyl)silyl]oxypropyl]-5-methoxyfuran-2-one
• CAS: 738604-49-4
• 化学式: C₂₄H₃₀O₄Si
• 分子量: 410.585
• InChiKey: YYYXQJOXEJWIQY-UHFFFAOYSA-N

物化性质

• 沸点：
  498.1±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyloxy-5H-furan-2-one 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 (2S*,3R*)-2-(2-hydroxyethyl)-3-hydroxytetrahydropyran
  参考文献：
  名称：

  呋喃对氧杂环的方法。第3部分：2,3-二取代的四氢吡喃的立体选择性合成

  摘要：

  基于呋喃环被单线态氧的氧化，使用高效的途径将可商购的呋喃1转化为2，3-反式和2，3-顺式-二取代的四氢吡喃2和3。四氢吡喃2和3可以通过柱色谱法轻松分离。

  DOI：

  10.1016/j.tet.2005.01.001
• 作为产物：
  描述：

  2-呋喃丙醇 在 咪唑 、 氧气 、 rose bengal 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyloxy-5H-furan-2-one
  参考文献：
  名称：

  呋喃对氧杂环的方法。第3部分：2,3-二取代的四氢吡喃的立体选择性合成

  摘要：

  基于呋喃环被单线态氧的氧化，使用高效的途径将可商购的呋喃1转化为2，3-反式和2，3-顺式-二取代的四氢吡喃2和3。四氢吡喃2和3可以通过柱色谱法轻松分离。

  DOI：

  10.1016/j.tet.2005.01.001

文献信息

• Cyclopentanone derivatives, method of synthesis and uses thereof
  申请人：Neuropharma S.A.

  公开号：EP1939192A1

  公开（公告）日：2008-07-02

  The present invention relates to cyclopentanone derivatives of formula (I), their method of synthesis and uses thereof. Concretely, the compounds disclosed have proved to be inhibitors of glycogen synthase kinase 3β, GSK-3 β, which is known to be involved in different disease and conditions, such as Alzheimer's disease or non-insulin dependent diabetes mellitus. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a GSK-3 mediated disease or condition.

  本发明涉及公式（I）的环戊酮衍生物，其合成方法及用途。具体来说，所披露的化合物已被证明是糖原合成酶激酶3β（GSK-3β）的抑制剂，GSK-3β已知参与不同疾病和病况，如阿尔茨海默病或非胰岛素依赖型糖尿病。本发明还涉及包含这些化合物的药物组合物。此外，本发明旨在将这些化合物用于制造治疗和/或预防GSK-3介导的疾病或病况的药物。
• The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles
  作者：Manuel Pérez、Pilar Canoa、Generosa Gómez、Carmen Terán、Yagamare Fall

  DOI：10.1016/j.tetlet.2004.05.035

  日期：2004.6

  We describe an efficient new approach for the synthesis of medium-size oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition. This present study enlarges the scope of the furan approach strategy for the synthesis of oxepanes. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthetic studies toward zoapatanol
  作者：Isela García、Manuel Pérez、Pedro Besada、Generosa Gómez、Yagamare Fall

  DOI：10.1016/j.tetlet.2007.12.088

  日期：2008.2

  The oxepane core of zoapatanol was efficiently synthesized from commercially available 1,2,4-butanetriol, and it was shown to be possible to introduce the angular methyl group at C2' by the reaction of an intermediate butenolide with diazomethane. (c) 2007 Elsevier Ltd. All rights reserved.
• New pyridazinone derivatives with vasorelaxant and platelet antiaggregatory activities
  作者：Tamara Costas、Pedro Besada、Alessandro Piras、Laura Acevedo、Matilde Yañez、Francisco Orallo、Reyes Laguna、Carmen Terán

  DOI：10.1016/j.bmcl.2010.09.031

  日期：2010.11

  New 6-substituted and 2,6-disubstituted pyridazinone derivatives were obtained starting from easily accessible alkyl furans by using oxidation with singlet oxygen to give 4-methoxy or 4-hydroxybutenolides, key intermediates of this synthetic strategy. The new pyridazinone derivatives have been studied as vasorelaxant and antiplatelet agents. Analysis of biological data revealed the silyl ethers (4a-i) and N,O-dibenzyl derivatives (6g-i) as the most active compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• The furan approach to oxacycles. Part 3: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans
  作者：David Alonso、Manuel Pérez、Generosa Gómez、Berta Covelo、Yagamare Fall

  DOI：10.1016/j.tet.2005.01.001

  日期：2005.2

  Commercially available furan 1 was converted to 2,3-trans and 2,3-cis-disubstituted tetrahydropyrans 2 and 3 using a highly efficient route to oxacycles, based on the oxidation of the furan ring with singlet oxygen. Tetrahydropyrans 2 and 3 could be easily separated by column chromatography.

  基于呋喃环被单线态氧的氧化，使用高效的途径将可商购的呋喃1转化为2，3-反式和2，3-顺式-二取代的四氢吡喃2和3。四氢吡喃2和3可以通过柱色谱法轻松分离。