methyl 3-(3-(2-methoxy-2-oxoethyl)-2-oxo-1-(2-(1-tosyl-1H-indol-3-yl)acetyl)piperidin-3-yl)-3-oxo-propanoate | 934586-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: methyl 3-(3-(2-methoxy-2-oxoethyl)-2-oxo-1-(2-(1-tosyl-1H-indol-3-yl)acetyl)piperidin-3-yl)-3-oxo-propanoate
• CAS: 934586-58-0
• 化学式: C₂₉H₃₀N₂O₉S
• 分子量: 582.631
• InChiKey: JOJXPGCZPMAZKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  146.12
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-(2-methoxy-2-oxoethyl)-2-oxo-1-(2-(1-tosyl-1H-indol-3-yl)acetyl)piperidin-3-yl)-3-oxo-propanoate 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以89%的产率得到methyl 2-diazo-3-(3-(2-methoxy-2-oxoethyl)-2-oxo-1-(2-(1-tosyl-1H-indol-3-yl)acetyl)piperidin-3-yl)-3-oxo-propanoate
  参考文献：
  名称：

  A dipolar cycloaddition approach toward the kopsifoline alkaloid framework

  摘要：

  Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole pi-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.064
• 作为产物：
  描述：

  2-氧-3-哌啶羧酸乙酯 在 4-二甲氨基吡啶 、 lithium hydroxide 、 正丁基锂 、 4 A molecular sieve 、 四丁基碘化铵 、 对甲苯磺酸 、 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 methyl 3-(3-(2-methoxy-2-oxoethyl)-2-oxo-1-(2-(1-tosyl-1H-indol-3-yl)acetyl)piperidin-3-yl)-3-oxo-propanoate
  参考文献：
  名称：

  A dipolar cycloaddition approach toward the kopsifoline alkaloid framework

  摘要：

  Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole pi-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.064

文献信息

• Cycloaddition Protocol for the Assembly of the Hexacyclic Framework Associated with the Kopsifoline Alkaloids
  作者：Xuechuan Hong、Stefan France、José M. Mejía-Oneto、Albert Padwa

  DOI：10.1021/ol062029z

  日期：2006.10.1

  An approach to the hexacyclic framework of the kopsifoline alkaloids has been developed and is based on a Rh(II)-catalyzed cyclization-cycloaddition cascade. The resulting [3+2]-cycloadduct was readily converted into the TBS enol ether 23. Oxidation of the primary alcohol present in 23 followed by reaction with CsF afforded compound 24 that contains the complete hexacyclic skeleton of the kopsifolines.