Oct-3-yn-2-yl 2-(1-methylindol-3-yl)acetate | 952718-84-2

• 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: Oct-3-yn-2-yl 2-(1-methylindol-3-yl)acetate
• 英文别名: oct-3-yn-2-yl 2-(1-methylindol-3-yl)acetate
• CAS: 952718-84-2
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: MIAUNZGTXVNCNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Oct-3-yn-2-yl 2-(1-methylindol-3-yl)acetate 在 platinum(II) chloride 一氧化碳 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以83%的产率得到
  参考文献：
  名称：

  PtCl₂-Catalyzed Rapid Access to Tetracyclic 2,3-Indoline-Fused Cyclopentenes:  Reactivity Divergent from Cationic Au(I) Catalysis and Synthetic Potential

  摘要：

  A PtCl2-catalyzed 3,3-rearrangement/[3+2]-cycloaddition of propargylic 3-indoleacetates is developed. Besides the efficient formation of highly functionalized tetracyclic cyclopentenes, the reaction is dramatically divergent from that catalyzed by cationic Au-I. Moreover, the synthetic potential of this method is demonstrated by a succinct synthesis of the tetracyclic core of vindolinine.

  DOI：

  10.1021/ja074536x
• 作为产物：
  描述：

  1-甲基-3-吲哚乙酸 、 3-辛炔-2-醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到Oct-3-yn-2-yl 2-(1-methylindol-3-yl)acetate
  参考文献：
  名称：

  PtCl₂-Catalyzed Rapid Access to Tetracyclic 2,3-Indoline-Fused Cyclopentenes:  Reactivity Divergent from Cationic Au(I) Catalysis and Synthetic Potential

  摘要：

  A PtCl2-catalyzed 3,3-rearrangement/[3+2]-cycloaddition of propargylic 3-indoleacetates is developed. Besides the efficient formation of highly functionalized tetracyclic cyclopentenes, the reaction is dramatically divergent from that catalyzed by cationic Au-I. Moreover, the synthetic potential of this method is demonstrated by a succinct synthesis of the tetracyclic core of vindolinine.

  DOI：

  10.1021/ja074536x

文献信息

• PtCl₂-Catalyzed Rapid Access to Tetracyclic 2,3-Indoline-Fused Cyclopentenes:  Reactivity Divergent from Cationic Au(I) Catalysis and Synthetic Potential
  作者：Guozhu Zhang、Vincent J. Catalano、Liming Zhang

  DOI：10.1021/ja074536x

  日期：2007.9.1

  A PtCl2-catalyzed 3,3-rearrangement/[3+2]-cycloaddition of propargylic 3-indoleacetates is developed. Besides the efficient formation of highly functionalized tetracyclic cyclopentenes, the reaction is dramatically divergent from that catalyzed by cationic Au-I. Moreover, the synthetic potential of this method is demonstrated by a succinct synthesis of the tetracyclic core of vindolinine.