2-(naphthalen-1-yl)-3-(propyn-1-yl)phenyl trifluoromethanesulfonate | 1138509-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-1-yl)-3-(propyn-1-yl)phenyl trifluoromethanesulfonate
• 英文别名: (2-Naphthalen-1-yl-3-prop-1-ynylphenyl) trifluoromethanesulfonate
• CAS: 1138509-40-6
• 化学式: C₂₀H₁₃F₃O₃S
• 分子量: 390.383
• InChiKey: HKWWMSCWPJYWCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-丙-1-炔基苯基)硼酸 、 2-(naphthalen-1-yl)-3-(propyn-1-yl)phenyl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 以45%的产率得到1-(2',3-di(propyn-1-yl)biphenyl-2-yl)naphthalene
  参考文献：
  名称：

  Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives

  摘要：

  [GRAPHICS]The new approach provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization. This sequence of reactions provides a synthetic route to helicenes in two steps from simply accessible building blocks. Furthermore, the method enables the introduction of substituents into the hexahelicene skeleton. The strategy developed is exemplified by the synthesis of 6,10-dimethylhexahelicene and 1-methoxy-6,10-dimethylhexahelicene.

  DOI：

  10.1021/jo900077j
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2-(naphthalen-1-yl)-3-(propyn-1-yl)phenol 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以75%的产率得到2-(naphthalen-1-yl)-3-(propyn-1-yl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives

  摘要：

  [GRAPHICS]The new approach provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization. This sequence of reactions provides a synthetic route to helicenes in two steps from simply accessible building blocks. Furthermore, the method enables the introduction of substituents into the hexahelicene skeleton. The strategy developed is exemplified by the synthesis of 6,10-dimethylhexahelicene and 1-methoxy-6,10-dimethylhexahelicene.

  DOI：

  10.1021/jo900077j

文献信息

• Synthesis of 2-Aza[6]helicene and Attempts To Synthesize 2,14-Diaza[6]helicene Utilizing Metal-Catalyzed Cycloisomerization
  作者：Jan Storch、Jan Čermák、Jindřich Karban、Ivana Císařová、Jan Sýkora

  DOI：10.1021/jo100252a

  日期：2010.5.7

  A modular synthetic approach leading to 2-aza[6]helicene is reported. It involves assembly of key hetero biphenylylnaphthalenes from functionalized building blocks and study of their metal catalyzed cycloisomerization.

  报道了导致2-氮杂[6]螺旋烯的模块化合成方法。它涉及从功能化的结构单元中组装关键的杂联苯苯基萘并研究其金属催化的环异构化。
• Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives
  作者：Jan Storch、Jan Sýkora、Jan Čermák、Jindřich Karban、Ivana Císařová、Aleš Růžička

  DOI：10.1021/jo900077j

  日期：2009.4.17

  [GRAPHICS]The new approach provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization. This sequence of reactions provides a synthetic route to helicenes in two steps from simply accessible building blocks. Furthermore, the method enables the introduction of substituents into the hexahelicene skeleton. The strategy developed is exemplified by the synthesis of 6,10-dimethylhexahelicene and 1-methoxy-6,10-dimethylhexahelicene.