3-(2-(phenylethynyl)phenyl)-1-(2-((2-(phenylethynyl)phenyl)ethynyl)phenyl)prop-2-yn-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-(2-(phenylethynyl)phenyl)-1-(2-((2-(phenylethynyl)phenyl)ethynyl)phenyl)prop-2-yn-1-ol
• 英文别名: 3-[2-(2-Phenylethynyl)phenyl]-1-[2-[2-[2-(2-phenylethynyl)phenyl]ethynyl]phenyl]prop-2-yn-1-ol；3-[2-(2-phenylethynyl)phenyl]-1-[2-[2-[2-(2-phenylethynyl)phenyl]ethynyl]phenyl]prop-2-yn-1-ol
• 化学式: C₃₉H₂₄O
• 分子量: 508.619
• InChiKey: DKUWZVFFPMJPQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-(phenylethynyl)phenyl)-1-(2-((2-(phenylethynyl)phenyl)ethynyl)phenyl)prop-2-yn-1-ol 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-phenyl-11H-indeno[1,2-g]naphtho[1,2-p]chrysene
  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
• 作为产物：
  描述：

  1-溴-2-苯基乙炔-苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-(2-(phenylethynyl)phenyl)-1-(2-((2-(phenylethynyl)phenyl)ethynyl)phenyl)prop-2-yn-1-ol
  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

• TRACELESS DIRECTING GROUPS IN RADICAL CASCADES: FROM OLIGOALKYNES TO FUSED HELICENES WITHOUT TETHERED INITATORS
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20160145276A1

  公开（公告）日：2016-05-26

  The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via β-scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows 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.

  本公开涉及一种在自由基级联中无痕定向基团。跳跃寡炔烃中的初始攻击的化学和区域选择性由丙炔烯氧基团控制。自由基转位导致自由基中心回到初始攻击点的回旋，它在级联的最后一步中通过β-裂解协助消除定向功能。在某些方面，本发明的反应由一种锡烷基团催化，它允许通过与亲电试剂以及Stille和Suzuki交叉偶联反应的简便反应进一步进行。这种选择性的自由基转化为控制跳跃寡炔烃转化为可调尺寸的多环核糖带提供了一种新方法。
• US9676679B2
  申请人：——

  公开号：US9676679B2

  公开（公告）日：2017-06-13
• 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.