3-<1-(tert-butyldimethylsilyloxy)vin-1-yl>furan | 174676-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-<1-(tert-butyldimethylsilyloxy)vin-1-yl>furan
• 英文别名: Tert-butyl((1-(furan-3-yl)vinyl)oxy)dimethylsilane；tert-butyl-[1-(furan-3-yl)ethenoxy]-dimethylsilane
• CAS: 174676-57-4
• 化学式: C₁₂H₂₀O₂Si
• 分子量: 224.375
• InChiKey: VMPIEJGHDOLUOT-UHFFFAOYSA-N

物化性质

• 沸点：
  235.0±15.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-<1-(tert-butyldimethylsilyloxy)vin-1-yl>furan 在 对苯二酚 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 4-oxo-4,5,6,7-tetrahydrobenzofuran-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Site Selectivity of the Diels−Alder Reactions of 3-[1-(tert-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans

  摘要：

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

  DOI：

  10.1021/jo951546k
• 作为产物：
  描述：

  1-(呋喃-3-基)乙醇 在 三乙胺 、 zinc(II) chloride 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 苯 为溶剂， 生成 3-<1-(tert-butyldimethylsilyloxy)vin-1-yl>furan
  参考文献：
  名称：

  （-）-正丙胺的立体选择性全合成，利用α-氯硫化物和亚磺胺用于CC键的形成†

  摘要：

  据报道，nuphar生物碱（-）-nupharamine的有效立体选择性合成。主要特征包括路易斯酸催化的α-氯硫化物与甲硅烷基乙烯酮缩醛的C–C键形成，烯丙基铟与亚磺胺的非对映选择性反应在C2处形成立体中心以及还原胺化，从而引入哌啶环的C6立体中心。

  DOI：

  10.1039/c5ob01750e

文献信息

• Site Selectivity of the Diels−Alder Reactions of 3-[1-(<i>tert</i>-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans
  作者：Aída Benítez、F. Ruth Herrera、Margarita Romero、Francisco X. Talamás、Joseph M. Muchowski

  DOI：10.1021/jo951546k

  日期：1996.1.1

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.
• Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation
  作者：Sadagopan Raghavan、Sheelamanthula Rajendar

  DOI：10.1039/c5ob01750e

  日期：——

  An efficient stereoselective synthesis of the nuphar alkaloid, (−)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C–C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the

  据报道，nuphar生物碱（-）-nupharamine的有效立体选择性合成。主要特征包括路易斯酸催化的α-氯硫化物与甲硅烷基乙烯酮缩醛的C–C键形成，烯丙基铟与亚磺胺的非对映选择性反应在C2处形成立体中心以及还原胺化，从而引入哌啶环的C6立体中心。