3-(tert-butyldiphenylsilyloxymethyl)furan | 117657-55-3

• 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: 3-(tert-butyldiphenylsilyloxymethyl)furan
• 英文别名: Tert-butyl-(furan-3-ylmethoxy)-diphenylsilane
• CAS: 117657-55-3
• 化学式: C₂₁H₂₄O₂Si
• 分子量: 336.506
• InChiKey: XRMLFDGTSGAJMG-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±34.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  3-(tert-butyldiphenylsilyloxymethyl)furan 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到[2-(tert-Butyl-diphenyl-silanyl)-furan-3-yl]-methanol
  参考文献：
  名称：

  The 1,4 O→C silyl migrations of various 3-[(trialkylsilyl)oxymethyl]-furans and -thiophenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)96838-2
• 作为产物：
  描述：

  [2-(tert-Butyl-diphenyl-silanyl)-furan-3-yl]-methanol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以89%的产率得到3-(tert-butyldiphenylsilyloxymethyl)furan
  参考文献：
  名称：

  Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O → C and [1,4] C → O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings

  摘要：

  [1,4] O --> C and [1,4] C --> O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy)methyl)furans and -thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl)furans and -thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1,4] O --> C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1,4] O --> C silyl migration to provide 2-silylated-3-furoic acids in moderate to good yield when treated with a mixture of LDA and HMPA. Finally, the above silyl migrations were shown to be reversible. Treatment of 2-silylated-3-(hydroxymethyl)furans and -thiophenes with NaH in DMF provided 3-((silyloxy)methyl)furans and -thiophenes in excellent yields via a [1,4] C --> O silyl migration. The [1,4] C --> O silyl migration was also shown to be an intramolecular process by a crossover study.

  DOI：

  10.1021/jo971097j

文献信息

• Synthesis of the C3–C7 fragment of tylonolide by the γ-hydroxybutenolide approach
  作者：William H. Miles、Cassidy M. Madison、Michael L. Mastria、Pui-In Tang

  DOI：10.1016/j.tetlet.2016.07.060

  日期：2016.8

  The seven-step synthesis of the C3–C7 fragment from 3-furanmethanol is described. The key step is an asymmetric aldol reaction of a γ-hydroxybutenolide with the titanium enolate of an N-propionyloxazolidinone. The resulting lactone was reduced to give the C4–C6 stereotriad, with further selective reductions to differentiate the two termini and C20 as a protected acetal.

  描述了从3-呋喃甲醇中七步合成C3-C7片段的过程。关键步骤是γ-羟基丁烯内酯与N-丙酰基恶唑烷酮的烯醇钛的不对称醛醇缩合反应。将生成的内酯还原成C4-C6立体三单元，进一步选择性还原以区分两个末端和C20作为受保护的缩醛。
• Novel Pyridazin-3(2<i>H</i>)-one-Based Guanidine Derivatives as Potential DNA Minor Groove Binders with Anticancer Activity
  作者：María Carmen Costas-Lago、Noemí Vila、Adeyemi Rahman、Pedro Besada、Isabel Rozas、José Brea、María Isabel Loza、Elisa González-Romero、Carmen Terán

  DOI：10.1021/acsmedchemlett.1c00633

  日期：2022.3.10

  Novel aryl guanidinium analogues containing the pyridazin-3(2H)-one core were proposed as minor groove binders (MGBs) with the support of molecular docking studies. The target dicationic or monocationic compounds, which show the guanidium group at different positions of the pyridazinone moiety, were synthesized using the corresponding silyl-protected pyridazinones as key intermediates. Pyridazinone

  在分子对接研究的支持下，提出了含有 pyridazin-3(2 H )-one 核心的新型芳基胍类似物作为小沟粘合剂 (MGBs)。使用相应的甲硅烷基保护的哒嗪酮作为关键中间体，合成了在哒嗪酮部分不同位置显示胍基的目标双阳离子或单阳离子化合物。哒嗪酮支架被转化为足够的溴代烷基衍生物，通过与N , N' - di -Boc-保护的胍反应，然后酸水解，以良好的收率提供盐酸盐1-14。新哒哒嗪3( 2H )的能力)-one-based 胍作为 DNA 粘合剂通过 DNA 紫外热变性实验进行了研究。还在三种癌细胞系（NCI-H460、A2780 和 MCF-7）中探索了它们的抗增殖活性。具有双胍结构的化合物1-4显示出较弱的 DNA 结合亲和力，并在所研究的三种癌细胞系中表现出合理的细胞活力抑制百分比。
• PYRIDAZIN-3(2H)-ONE DERIVATIVES WHICH ARE SELECTIVE INHIBITORS OF THE ISOFORM B OF MONOAMINE OXIDASE
  申请人：Universidad de Vigo

  公开号：EP3115359B1

  公开（公告）日：2019-11-13
• New platelet aggregation inhibitors based on pyridazinone moiety
  作者：Tamara Costas、María Carmen Costas-Lago、Noemí Vila、Pedro Besada、Ernesto Cano、Carmen Terán

  DOI：10.1016/j.ejmech.2015.02.061

  日期：2015.4

  New series of pyridazinone derivatives (4, 5 and 6) were synthesized in good yields following a synthetic strategy based on singlet oxygen oxidation of alkyl furans, in which a suitable beta(alpha)-substituted gamma-hydroxybutenolide (10 or 11) or a bicyclic lactone (12 or 13) was the key intermediate. The synthesized compounds were tested in vitro as antiplatelet agents and some of them (compounds 4b, 4d and 5b) exhibited potent inhibitory effects on collagen-induced platelet aggregation with IC50 values in the low mu M range. Studies performed with the most active compound of these series (4b) demonstrated its lack of activity as inhibitor of platelet aggregation induced by other agonists as thrombin, ionomycin or U-46619 suggesting a selective action on the biochemical mechanisms triggered by collagen in the platelets. (C) 2015 Elsevier Masson SAS. All rights reserved.
• The 1,4 C→O silyl migrations of various furan and thiophene systems
  作者：Patrick G. Spinazzé、Brian A. Keay

  DOI：10.1016/s0040-4039(00)99574-1

  日期：——