11-butyl-11H-benzo[a]fluorene | 88223-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 11-butyl-11H-benzo[a]fluorene
• 英文别名: 11-Butyl-11H-benzo[a]fluorene
• CAS: 88223-20-5
• 化学式: C₂₁H₂₀
• 分子量: 272.39
• InChiKey: LGVXWGCCTKVKNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(hex-1-yn-1-yl)-2-(1-methoxy-3-(phenyl)prop-2-yn-1-yl)benzene 在 偶氮二异丁腈 、 三正丁基氢锡 、 盐酸 作用下， 以 甲苯 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 以70%的产率得到11-butyl-11H-benzo[a]fluorene
  参考文献：
  名称：

  Traceless Directing Groups in Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators

  摘要：

  We report the first example of a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by propargyl OR moiety. Radical translocations lead to the boomerang return of the radical center to the site of initial attack where it assists the elimination of the directing functionality via β-scission in the last step of the cascade. The Bu3Sn moiety continues further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

  DOI：

  10.1021/ja510563d

文献信息

• Solov'yanov, A. A.; Beletskaya, I. P.; Reutov, O. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 1592 - 1603
  作者：Solov'yanov, A. A.、Beletskaya, I. P.、Reutov, O. A.

  DOI：——

  日期：——
• Traceless Directing Groups in Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators
  作者：Kamalkishore Pati、Gabriel dos Passos Gomes、Trevor Harris、Audrey Hughes、Hoa Phan、Tanmay Banerjee、Kenneth Hanson、Igor V. Alabugin

  DOI：10.1021/ja510563d

  日期：2015.1.28

  We report the first example of a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by propargyl OR moiety. Radical translocations lead to the boomerang return of the radical center to the site of initial attack where it assists the elimination of the directing functionality via β-scission in the last step of the cascade. The Bu3Sn moiety continues further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.