2-[1-[Tert-butyl(dimethyl)silyl]oxy-6-trimethylsilyl-5-(trimethylsilylmethyl)hex-4-en-2-yl]isoindole-1,3-dione | 185814-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[1-[Tert-butyl(dimethyl)silyl]oxy-6-trimethylsilyl-5-(trimethylsilylmethyl)hex-4-en-2-yl]isoindole-1,3-dione
• CAS: 185814-77-1
• 化学式: C₂₇H₄₇NO₃Si₃
• 分子量: 517.932
• InChiKey: DHPHTXXSDSUKOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[1-[Tert-butyl(dimethyl)silyl]oxy-6-trimethylsilyl-5-(trimethylsilylmethyl)hex-4-en-2-yl]isoindole-1,3-dione 在 一水合肼 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 4.75h， 生成 Tert-butyl-[2-isocyano-6-trimethylsilyl-5-(trimethylsilylmethyl)hex-4-enoxy]-dimethylsilane
  参考文献：
  名称：

  Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2H-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations

  摘要：

  2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.

  DOI：

  10.1021/jo961452q
• 作为产物：
  描述：

  (E)-4-((tert-butyldimethylsilyl)oxy)but-2-enal 在 bis-triphenylphosphine-palladium(II) chloride 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-[1-[Tert-butyl(dimethyl)silyl]oxy-6-trimethylsilyl-5-(trimethylsilylmethyl)hex-4-en-2-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2H-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations

  摘要：

  2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.

  DOI：

  10.1021/jo961452q

文献信息

• Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2<i>H</i>-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations
  作者：Timothy Kercher、Tom Livinghouse

  DOI：10.1021/jo961452q

  日期：1997.2.1

  2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.