2,2-dimethyl-1-[4-(3-trimethylsilylprop-1-en-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]propan-1-one | 185814-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,2-dimethyl-1-[4-(3-trimethylsilylprop-1-en-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]propan-1-one
• CAS: 185814-47-5
• 化学式: C₁₅H₂₇NOSi
• 分子量: 265.471
• InChiKey: MBLCDBSSIJPTFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1-[4-(3-trimethylsilylprop-1-en-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]propan-1-one 在 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,2-dimethyl-1-[(2S,3S)-1-(4-methylphenyl)sulfonyl-3-(3-trimethylsilylprop-1-en-2-yl)pyrrolidin-2-yl]propan-1-one
  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：

  5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-en-1-amine 在 silver trifluoromethanesulfonate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 2,2-dimethyl-1-[4-(3-trimethylsilylprop-1-en-2-yl)-3,4-dihydro-2H-pyrrol-5-yl]propan-1-one
  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.