tetrahydropyranyl ether of 2-thiophenemethanol | 121851-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tetrahydropyranyl ether of 2-thiophenemethanol
• 英文别名: 2-(Thiophen-2-ylmethoxy)oxane
• CAS: 121851-24-9
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: SRLBYEMUZMUHSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetrahydropyranyl ether of 2-thiophenemethanol 在 ammonium cerium(IV) nitrate 作用下， 以 alkaline aq. solution 、 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到2-噻吩甲醇
  参考文献：
  名称：

  Remarkable deprotection of THP and THF ethers catalysed by cerium ammonium nitrate (CAN) under neutral conditions

  摘要：

  The catalytic deprotection of a range of functionalised THP and THF ethers can be efficiently performed, under neutral conditions, using as little as 3 mol% CAN in MeCN/borate buffer (pH = 8). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01043-6
• 作为产物：
  描述：

  2-噻吩甲醇 、 3,4-二氢-2H-吡喃 在 ammonium cerium(IV) nitrate 、 1-butylpyridinium tetrachloroferrate(III) 作用下， 反应 0.5h， 以88%的产率得到tetrahydropyranyl ether of 2-thiophenemethanol
  参考文献：
  名称：

  Efficient and Convenient Procedure for Protection of Hydroxyl Groups to the THP, THF and TMS Ethers and Oxidation of these Ethers to their Aldehydes or Ketones in [BPy]FeCl₄ as a Low Cost Room Temperature Ionic Liquid

  摘要：

  醇类在1-丁基吡啶氯铁介质中被转化为相应的THP、THF或TMS醚，产率高至极好。这是一种稳定且低成本的室温离子液体。此外，在这种离子液体中，这些醚被氧化为它们的醛或酮，而没有发生任何过氧化反应。

  DOI：

  10.1515/znb-2006-0313

文献信息

• A Mild, Efficient and Sustainable Tetrahydropyranylation of Alcohols Promoted by Acidic Natural Deep Eutectic Solvents
  作者：Davide Arnodo、Eugenio De Nardo、Simone Ghinato、Salvatore Baldino、Marco Blangetti、Cristina Prandi

  DOI：10.1002/cssc.202202066

  日期：2023.2.8

  A simple, scalable, and sustainable access to tetrahydropyranyl (THP) ethers from alcohols was achieved exploiting the dual role of acidic natural deep eutectic solvents (NADESs) both as catalysts and reaction media, working under bench-type and mild reaction conditions. The easy scalability of the process and the recyclability of the NADES add great value in terms of efficiency and environmentally

  利用酸性天然低共熔溶剂 (NADES) 作为催化剂和反应介质的双重作用，在工作台型和温和的反应条件下，实现了从醇中获取四氢吡喃 (THP) 醚的简单、可扩展且可持续的途径。该过程的轻松可扩展性和 NADES 的可回收性在效率和环境可持续性方面增加了巨大的价值。
• Crisp, Geoffrey T., Synthetic Communications, 1989, vol. 19, # 1, 2, p. 307 - 316
  作者：Crisp, Geoffrey T.

  DOI：——

  日期：——
• Novel protein kinase C inhibitors: synthesis and PKC inhibition of β-substituted polythiophene derivatives
  作者：Wei-Chu Xu、Qin Zhou、Curtis L. Ashendel、Ching-te Chang、Ching-jer Chang

  DOI：10.1016/s0960-894x(99)00375-3

  日期：1999.8

  A series of beta-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of alpha-terthiophene were potent PKC inhibitors (IC50 = 10(-7) M). (C) 1999 Elsevier Science Ltd. All rights reserved.
• GEOFFREY, GEOFFEREY T., SYNTH. COMMUN., 19,(1989) N-2, C. 307-316
  作者：GEOFFREY, GEOFFEREY T.

  DOI：——

  日期：——