2-(tert-butyldiphenylsilyloxy-propan-1'-yl)-furan | 738604-46-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(tert-butyldiphenylsilyloxy-propan-1'-yl)-furan
• 英文别名: 2-(3-tert-butyldiphenylsilyloxypropyl)furan；tert-Butyl-(3-furan-2-yl-propoxy)-diphenyl-silane；2-[3-(t-butyldiphenylsilyloxy)propyl]furan；Tert-butyl-[3-(furan-2-yl)propoxy]-diphenylsilane
• CAS: 738604-46-1
• 化学式: C₂₃H₂₈O₂Si
• 分子量: 364.56
• InChiKey: AQCPAOKJBLPLCD-UHFFFAOYSA-N

物化性质

• 沸点：
  424.9±37.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldiphenylsilyloxy-propan-1'-yl)-furan 在 palladium (II) hydroxide on carbon 氢气 、 叔丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 正戊烷 为溶剂， 反应 52.0h， 生成 5-(3'-tert-butyldiphenylsilyloxy-propan-1'-yl)-2-(4-hydroxy-butan-1'-yl)-furan
  参考文献：
  名称：

  级联自由基介导的环化反应，使用共轭ynone电泳。一种合成类固醇和其他新型环稠合多环碳环化合物的方法。

  摘要：

  与碘二烯酮16b的级联自由基介导的Diels-Alder反应产生了三环酮17（22％）。相比之下，用Bu（3）SnH-AIBN处理取代的呋喃36和47分别导致四环化合物44和58，而不是预期的雌激素，即38和48。在另一项研究中，尝试了级联自由基-由邻芳基取代的碘二烯酮72和73介导的环化反应，最终导致环D芳族甾体7取代，分别给出大环酮76或新型桥联三环77/82，这取决于是使用苯还是庚烷作为溶剂在反应中。

  DOI：

  10.1039/b703373g
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 2,2'-联吡啶 、 正丁基锂 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 2-(tert-butyldiphenylsilyloxy-propan-1'-yl)-furan
  参考文献：
  名称：

  The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.05.035

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. 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。
• Synthesis and complete assignment of the 1H and 13C NMR spectra of 6-substituted and 2,6-disubstituted pyridazin-3(2H)-ones
  作者：Pedro Besada、Tamara Costas、Noemi Vila、Carla Chessa、Carmen Terán

  DOI：10.1002/mrc.2755

  日期：2011.7

  Several pyridazin‐3(2H)‐one derivatives were synthesized starting from alkyl furans using oxidation with singlet oxygen to give 4‐methoxy or 4‐hydroxybutenolides, key intermediates of the synthetic strategy followed. For all pyridazinones reported, a complete assignment of the 1H and 13C NMR spectra using one‐ and two‐dimensional NMR spectroscopic methods, which included NOE, DEPT, COSY, HSQC and HMBC

  以烷基呋喃为原料，用单线态氧氧化得到 4-甲氧基或 4-羟基丁烯内酯，合成了几种哒嗪-3(2H)-酮衍生物，随后是合成策略的关键中间体。对于所有报道的哒嗪酮，使用一维和二维 NMR 光谱方法（包括 NOE、DEPT、COSY、HSQC 和 HMBC 实验）完成了 1H 和 13C NMR 光谱的完整分配。分析了杂环原子的化学位移与 N-2 和 C-6 上的取代基之间的相关性。版权所有 © 2011 John Wiley & Sons, Ltd.
• Use of Ionic Liquid as Solvent in the Oxidation of Furans with Singlet Oxygen
  作者：Yagamare Fall、Alioune Fall、Massène Sène、Emilia Tojo、Generosa Gómez

  DOI：10.1055/s-0030-1258211

  日期：2010.10

  The photocatalytic oxidation of a furan to a hydroxybutenolide in good yield is the first step of a one-pot synthesis of a γ-substituted α,β-unsaturated γ-butyrolactone in the ionic liquid 1-hexyl-3-methylimidazolium chloride ([HMIM][Cl]).

  在离子液体 1-hexyl-3-methylimidazolium chloride ([HMIM][Cl])中，通过光催化将呋喃氧化成羟基丁烯内酯，并获得良好的收率，这是一步法合成δ-取代的δ±,δ-不饱和δ-丁内酯的第一步。
• 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.