2-allyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2-prop-2-enyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole；1-(4-methylphenyl)sulfonyl-2-prop-2-enyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• 化学式: C₂₄H₂₈BNO₄S
• 分子量: 437.368
• InChiKey: ZOWRWGCIRQCTJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  钯催化合成二氢环辛八烯[ b ]吲哚及其与马来酰亚胺或马来酸酐的热反应性

  摘要：

  AbstractA palladium(0)‐catalyzed reaction of 2‐allyl‐3‐indolyl boronates/propargylic carbonates was observed to afford dihydrocycloocta[b]indoles highly efficiently via carbon‐carbon coupling, [1,5]‐hydrogen migration involving dearomatization, and electrocyclization involving rearomatization. Their thermal reactions with the addition of dienophiles involving eletrocyclization and [4+2] cycloaddition have been studied.magnified image

  DOI：

  10.1002/adsc.201400644
• 作为产物：
  描述：

  1-戊烯-4-炔 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 53.5h， 生成 2-allyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole
  参考文献：
  名称：

  钯催化合成二氢环辛八烯[ b ]吲哚及其与马来酰亚胺或马来酸酐的热反应性

  摘要：

  AbstractA palladium(0)‐catalyzed reaction of 2‐allyl‐3‐indolyl boronates/propargylic carbonates was observed to afford dihydrocycloocta[b]indoles highly efficiently via carbon‐carbon coupling, [1,5]‐hydrogen migration involving dearomatization, and electrocyclization involving rearomatization. Their thermal reactions with the addition of dienophiles involving eletrocyclization and [4+2] cycloaddition have been studied.magnified image

  DOI：

  10.1002/adsc.201400644

文献信息

• Studies on Palladium-Catalyzed Synthesis of Dihydrocycloocta- [<i>b</i>]indoles and their Thermal Reactivities with Maleimide or Maleic Anhydride
  作者：Can Zhu、Shengming Ma

  DOI：10.1002/adsc.201400644

  日期：2014.12.15

  AbstractA palladium(0)‐catalyzed reaction of 2‐allyl‐3‐indolyl boronates/propargylic carbonates was observed to afford dihydrocycloocta[b]indoles highly efficiently via carbon‐carbon coupling, [1,5]‐hydrogen migration involving dearomatization, and electrocyclization involving rearomatization. Their thermal reactions with the addition of dienophiles involving eletrocyclization and [4+2] cycloaddition have been studied.magnified image