3-(Bromomethyl)-4-[3-(bromomethyl)phenanthren-4-yl]phenanthrene | 221683-80-3

• 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: 3-(Bromomethyl)-4-[3-(bromomethyl)phenanthren-4-yl]phenanthrene
• CAS: 221683-80-3
• 化学式: C₃₀H₂₀Br₂
• 分子量: 540.297
• InChiKey: GQYMFYLNCSOXAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(Bromomethyl)-4-[3-(bromomethyl)phenanthren-4-yl]phenanthrene 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 0.17h， 以75%的产率得到庚螺烯
  参考文献：
  名称：

  Synthesis of carbohelicenes and derivatives by “carbenoid couplings”

  摘要：

  Short synthetic sequences to carbohelicenes have been achieved under thermal conditions, without using photochemistry and high dilution. Couplings of aromatic bis(bromomethyl) moieties, in the presence of an excess of LiHMDS, are key reactions in the final ring closures to carbohelicenes. These optimized, quick and efficient reactions occur at 0 degrees C within 10 min, and often provide [5]-helicene, [5] helicene derivatives and [7]-helicene in similar to 75% yield. Preliminary data questioned the formation of carbenoid anions and carbenes in the so called "carbenoid couplings". (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02670-7
• 作为产物：
  描述：

  (R)-(-)-3,3'-bis(trifluoromethanesulfonyloxy)-4,4'-biphenanthryl 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) N-溴代丁二酰亚胺(NBS) 、 (PhCO₂)2O 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 1.25h， 生成 3-(Bromomethyl)-4-[3-(bromomethyl)phenanthren-4-yl]phenanthrene
  参考文献：
  名称：

  Synthesis of carbohelicenes and derivatives by “carbenoid couplings”

  摘要：

  Short synthetic sequences to carbohelicenes have been achieved under thermal conditions, without using photochemistry and high dilution. Couplings of aromatic bis(bromomethyl) moieties, in the presence of an excess of LiHMDS, are key reactions in the final ring closures to carbohelicenes. These optimized, quick and efficient reactions occur at 0 degrees C within 10 min, and often provide [5]-helicene, [5] helicene derivatives and [7]-helicene in similar to 75% yield. Preliminary data questioned the formation of carbenoid anions and carbenes in the so called "carbenoid couplings". (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02670-7