(RS)-10-(2’-(ethynyl)naphthalen-1’-yl)benzo[h]quinoline | 1427675-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (RS)-10-(2’-(ethynyl)naphthalen-1’-yl)benzo[h]quinoline
• 英文别名: 10-(2-Ethynylnaphthalen-1-yl)benzo[h]quinoline；10-(2-ethynylnaphthalen-1-yl)benzo[h]quinoline
• CAS: 1427675-51-1；1428134-14-8；1428134-15-9
• 化学式: C₂₅H₁₅N
• 分子量: 329.401
• InChiKey: CZYYZJDVMRHOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (RS)-10-(2’-(ethynyl)naphthalen-1’-yl)benzo[h]quinoline 在 氯化铂 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以65%的产率得到(M)-1-aza[6]helicene
  参考文献：
  名称：

  A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy

  摘要：

  A rapid route to diversely functionalized 1-aza[6]helicenes has been achieved via the development of a copper-mediated cross-coupling reaction, followed by PtCl4-catalyzed cycloisomerization. Not only does this method allow access to these functionally important molecules on gram scale, but this strategy Is also suitable for relaying the axial chirality of a key intermediate to the helicity of the product.

  DOI：

  10.1021/ol400493x
• 作为产物：
  描述：

  1-溴-2-萘酚 在 吡啶 、 盐酸 、 copper(l) iodide 、 正丁基锂 、 乙基溴化镁 、 四丁基氟化铵 、 水 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (RS)-10-(2’-(ethynyl)naphthalen-1’-yl)benzo[h]quinoline
  参考文献：
  名称：

  A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy

  摘要：

  A rapid route to diversely functionalized 1-aza[6]helicenes has been achieved via the development of a copper-mediated cross-coupling reaction, followed by PtCl4-catalyzed cycloisomerization. Not only does this method allow access to these functionally important molecules on gram scale, but this strategy Is also suitable for relaying the axial chirality of a key intermediate to the helicity of the product.

  DOI：

  10.1021/ol400493x

文献信息

• A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy
  作者：Marko Weimar、Rosenildo Correa da Costa、Fu-Howe Lee、Matthew J. Fuchter

  DOI：10.1021/ol400493x

  日期：2013.4.5

  A rapid route to diversely functionalized 1-aza[6]helicenes has been achieved via the development of a copper-mediated cross-coupling reaction, followed by PtCl4-catalyzed cycloisomerization. Not only does this method allow access to these functionally important molecules on gram scale, but this strategy Is also suitable for relaying the axial chirality of a key intermediate to the helicity of the product.