4-(1-tert-butylindol-3-yl)-4-oxo-(2E)-butenoic acid methyl ester | 1428884-13-2

• 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: 4-(1-tert-butylindol-3-yl)-4-oxo-(2E)-butenoic acid methyl ester
• 英文别名: methyl (E)-4-(1-tert-butylindol-3-yl)-4-oxobut-2-enoate
• CAS: 1428884-13-2
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: YUCWENRUPKWQMK-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-tert-butyl-1H-indole 、 一氧化碳 、 丙炔酸甲酯 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 为溶剂， 105.0 ℃ 、2.07 MPa 条件下， 反应 15.0h， 以77%的产率得到4-(1-tert-butylindol-3-yl)-4-oxo-(2E)-butenoic acid methyl ester
  参考文献：
  名称：

  Pd-Catalyzed Direct Coupling of Indoles with Carbon Monoxide and Alkynes: Selective Synthesis of Linear α,β-Unsaturated Ketones

  摘要：

  A new strategy is described for the direct coupling of indoles with CO and alkynes to generate alpha,beta-unsaturated ketones. This procedure, employing Xantphos and Pd(CH3CN)(4)(BF4)(2), is attractive from both environmental and operational points of view and adds value to the method for the carbonylation of alkynes by using carbon nucleophiles and affording linear regioselectivity.

  DOI：

  10.1021/ol400722h

文献信息

• Pd-Catalyzed Direct Coupling of Indoles with Carbon Monoxide and Alkynes: Selective Synthesis of Linear α,β-Unsaturated Ketones
  作者：Fanlong Zeng、Howard Alper

  DOI：10.1021/ol400722h

  日期：2013.4.19

  A new strategy is described for the direct coupling of indoles with CO and alkynes to generate alpha,beta-unsaturated ketones. This procedure, employing Xantphos and Pd(CH3CN)(4)(BF4)(2), is attractive from both environmental and operational points of view and adds value to the method for the carbonylation of alkynes by using carbon nucleophiles and affording linear regioselectivity.