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 | 833436-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 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}-2-diazo-3-oxo-propionic acid methyl ester
• CAS: 833436-56-9
• 化学式: C₃₀H₄₂N₄O₆Si
• 分子量: 582.772
• InChiKey: CXQPFXCPBJNVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131.31
• 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}-2-diazo-3-oxo-propionic acid methyl ester 在 [(C₇H₁₅CO₂)4Rh₂] 作用下， 以 苯 为溶剂， 以74%的产率得到methyl (1R,2S,10R,17S,18S)-17-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-3-methyl-12,20-dioxo-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate
  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 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 、 乙腈 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}-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