9,10-dihydrophenanthrene-3-carbonitrile | 1533438-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,10-dihydrophenanthrene-3-carbonitrile
• 英文别名: 9,10-Dihydrophenanthrene-3-carbonitrile
• CAS: 1533438-59-3
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: JKCYBACAGMZLLB-UHFFFAOYSA-N

物化性质

• 沸点：
  378.3±21.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氰基苯乙烯 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到9,10-dihydrophenanthrene-3-carbonitrile
  参考文献：
  名称：

  Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes

  摘要：

  A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced,1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.

  DOI：

  10.1021/ol4033094

文献信息

• Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes
  作者：Sachin Suresh Bhojgude、Anup Bhunia、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/ol4033094

  日期：2014.2.7

  A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced,1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.