3-{3-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-1-[2-(1-methyl-1H-indol-3-yl)-acetyl]-2-oxo-piperidin-3-yl}-3-oxo-propionic acid methyl ester | 833436-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-{3-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-1-[2-(1-methyl-1H-indol-3-yl)-acetyl]-2-oxo-piperidin-3-yl}-3-oxo-propionic acid methyl ester
• CAS: 833436-55-8
• 化学式: C₃₀H₄₄N₂O₆Si
• 分子量: 556.775
• InChiKey: ZPMYKOVDELVGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-{3-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-1-[2-(1-methyl-1H-indol-3-yl)-acetyl]-2-oxo-piperidin-3-yl}-3-oxo-propionic acid methyl ester 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 以98%的产率得到3-{3-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-1-[2-(1-methyl-1H-indol-3-yl)-acetyl]-2-oxo-piperidin-3-yl}-2-diazo-3-oxo-propionic acid methyl ester
  参考文献：
  名称：

  Skeletal Diversity via a Folding Pathway:  Synthesis of Indole Alkaloid-Like Skeletons

  摘要：

  Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.

  DOI：

  10.1021/ol047945w
• 作为产物：
  描述：

  2-氧-3-哌啶羧酸乙酯 在 lithium hydroxide 、 正丁基锂 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 3-{3-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-1-[2-(1-methyl-1H-indol-3-yl)-acetyl]-2-oxo-piperidin-3-yl}-3-oxo-propionic acid methyl ester
  参考文献：
  名称：

  Skeletal Diversity via a Folding Pathway:  Synthesis of Indole Alkaloid-Like Skeletons

  摘要：

  Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.

  DOI：

  10.1021/ol047945w