tanakine | 106449-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tanakine
• 英文别名: 1-(1H-indol-3-yl)-3-methylbutane-2,3-diol
• CAS: 106449-15-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: JPRWHAIHJJJQTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  actinopolymorphol B 在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以60%的产率得到tanakine
  参考文献：
  名称：

  Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

  摘要：

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.010

文献信息

• Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products
  作者：Daniel Zárate-Zárate、Raúl Aguilar、R. Israel Hernández-Benitez、Ehecatl M. Labarrios、Francisco Delgado、Joaquín Tamariz

  DOI：10.1016/j.tet.2015.07.010

  日期：2015.9

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.