1-(1-methoxyprop-2-yn-1-yl)-2-(phenylethynyl)benzene | 1215270-06-6

• 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: 1-(1-methoxyprop-2-yn-1-yl)-2-(phenylethynyl)benzene
• 英文别名: 1-(1-methoxyprop-2-ynyl)-2-(2-phenylethynyl)benzene
• CAS: 1215270-06-6
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: NTMGBOFTAOQSLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘苯 、 1-(1-methoxyprop-2-yn-1-yl)-2-(phenylethynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 三乙胺 、 甲苯 为溶剂， 以95%的产率得到1-(1-methoxy-3-phenylprop-2-yn-1-yl)-2-(phenylethynyl)benzene
  参考文献：
  名称：

  通过钯催化偶联，炔丙基-烯丙基异构化和施密特环化序列轻松合成多环芴衍生物

  摘要：

  已经实现了涉及Sonogashira偶联，炔丙基-烯基异构化和Schmittel环化的逐步过程，从而导致了从容易获得的起始原料有效合成多环芴衍生物的方法。该反应的特征是在一个操作步骤中形成了三个新的碳-碳键以构建苯单元，以及三个或四个环的有效组装。

  DOI：

  10.1002/adsc.200900600
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.92h， 生成 1-(1-methoxyprop-2-yn-1-yl)-2-(phenylethynyl)benzene
  参考文献：
  名称：

  将无痕导向基团与自由基反应性的杂化控制相结合：从跳过的炔烃到无缺陷的六边形骨架

  摘要：

  该工作公开了用于将低炔烃转化为无五边形缺陷的多芳族多环体系的第一种通用解决方案。该级联反应的效率和选择性源自Bu 3的组合Sn介导的TDG（无痕导向基团）跳过的炔烃的级联转化，其中关键自由基前体的反应性因杂交效应而受到抑制。这种方法可确保最终结构仅包含六元环。通过在多米诺骨牌转化中引入适当取代的烯烃作为最终单元，可以轻松实现该策略的实际实施。该策略为聚芳烃带的可控制备开辟了一条新途径。所得的酯官能度可用于额外的Friedel-Crafts环闭合，该闭合可有效地使两个额外的具有独特电子特征的循环与自由基级联形成的扩展芳族体系退火。

  DOI：

  10.1002/anie.201605799

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。
• Cobalt-catalyzed regioselective syntheses of indeno[2,1-<i>c</i>]pyridines from nitriles and diynes bearing propargyl fragments
  作者：Murong Xu、Zhong Zheng、Mengdan Wang、Lingkai Kong、Yujuan Ao、Yanzhong Li

  DOI：10.1039/c8ob02419g

  日期：——

  highly efficient CoI2/o-phenanthroline catalyzed cycloaddition reaction of diynes bearing TBS protected propargylic alcohol fragments with nitriles has been developed. This methodology offers regioselective access, with good functional group tolerance, to various indeno[2,1-c]pyridine derivatives in moderate to excellent yields. It was found that o-phenanthroline as a bidentate nitrogen ligand showed

  已开发出一种高效的CoI 2 /邻菲咯啉催化带有TBS保护的炔丙醇片段的丁炔与腈的环加成反应。该方法以中等至优异的产率提供了对多种茚并[2,1- c ]吡啶衍生物的区域选择性通路，具有良好的官能团耐受性。发现邻菲咯啉作为二齿氮配体在该环加成反应中显示出高功效。
• 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.
• Gold-catalyzed cyclization of propargylic diynes: Ethers vs acetates – Related products but different pathways
  作者：Johannes Schädlich、Tobias Lauterbach、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1016/j.jorganchem.2015.04.053

  日期：2015.10

  Diyne substrates bearing one propargylic ether instead of the previously published propargylic acetates were subjected to a gold catalyst. alpha-Naphthol derivatives were obtained as products of the cycloisomerization. The close relationship of the products to the corresponding cyclizations implicated a related mechanistic scenary at first, but further studies favour a mechanistic pathway that is completely different. (C) 2015 Elsevier B.V. All rights reserved.
• US9676679B2
  申请人：——

  公开号：US9676679B2

  公开（公告）日：2017-06-13