1-iodo-8-(trimethylsilylethynyl)naphthalene | 192384-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-iodo-8-(trimethylsilylethynyl)naphthalene
• 英文别名: Silane, [(8-iodo-1-naphthalenyl)ethynyl]trimethyl-；2-(8-iodonaphthalen-1-yl)ethynyl-trimethylsilane
• CAS: 192384-39-7
• 化学式: C₁₅H₁₅ISi
• 分子量: 350.274
• InChiKey: GZKLMXFEGSQTOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-iodo-8-(trimethylsilylethynyl)naphthalene 在 tris-(dibenzylideneacetone)dipalladium(0) 三苯胂 、 四丁基氟化铵 、 对苯二酚 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 xylene 为溶剂， 反应 26.0h， 生成 荧蒽
  参考文献：
  名称：

  Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes

  摘要：

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

  DOI：

  10.1021/jo9717853
• 作为产物：
  描述：

  1,8-二碘萘 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 二乙胺 为溶剂， 生成 1-iodo-8-(trimethylsilylethynyl)naphthalene
  参考文献：
  名称：

  通过双（8-乙炔基-1-萘基）乙炔的热异构化轻松形成ena [1,2- a ] py结构

  摘要：

  将标题的1,8-萘-乙炔化合物进行热异构化为[1,2- a ] py衍生物，并通过X射线分析建立了新的多环芳族体系的结构。异构化的机理通过依次通过双自由基中间体进行环化反应以及随后的氢迁移来解释。

  DOI：

  10.1016/j.tetlet.2006.08.011

文献信息

• Nickel-Catalyzed, Cascade Cycloadditions of 1-Ethynyl-8-halonaphthalenes with Nitriles: Synthesis, Structure, and Physical Properties of New Pyrroloarenes
  作者：Tsun-Cheng Wu、Chia-Cheng Tai、Hsin-Chieh Tiao、Ming-Yu Kuo、Yao-Ting Wu

  DOI：10.1002/chem.201002905

  日期：2011.2.7

  The reaction of 1‐ethynyl‐8‐halonaphthalenes 1 with nitriles in the presence of the catalytic system [NiBr2(dppe)]/Zn (dppe=1,2‐bis(diphenylphosphino)ethane) is found to produce unusual pyrroloarenes 2. The carbon–nitrogen triple bond in nitrile is activated twice, and five new bonds are formed in a one‐pot transformation, which causes a pyrrole and two six‐membered rings to be generated simultaneously

  在催化体系[NiBr 2（dppe）] / Zn（dppe = 1,2-双（二苯基膦基）乙烷）的存在下，1-乙炔基-8-卤代萘1与腈的反应会产生不寻常的吡咯并芳烃2。腈中的碳-氮三键被激活两次，并且在一个一键转换中形成五个新键，这导致同时生成吡咯和两个六元环。检查了该反应的范围和局限性。同样，烷基桥连的二炔也可提供相应的多环。由于芳基旋转的限制，二芳基取代的环加合物2（R 1 = Ar）是助熔剂。通过执行1研究旋转壁垒在各种温度下的1 H NMR实验。几种化合物的结构是通过X射线晶体学分析确定的。还研究了吡咯并芳烃的光物理和电化学性质。
• Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes
  作者：Tsun-Cheng Wu、Chia-Hua Chen、Daijiro Hibi、Akihiro Shimizu、Yoshito Tobe、Yao-Ting Wu

  DOI：10.1002/anie.201001929

  日期：2010.9.17

  Zethrenes were synthesized by Pd‐catalyzed cyclodimerization of 1‐ethynyl‐8‐iodonaphthalenes. The structure of these cycloadducts was confirmed by X‐ray crystal analysis. The bond lengths and bond alternation in the crystal structures reveal that the central two six‐membered rings of the title compounds lack aromaticity.

  蒽通过Pd催化的1-乙炔基-8-碘萘的环二聚反应合成。X射线晶体分析证实了这些环加合物的结构。晶体结构中的键长和键交替表明标题化合物的中心两个六元环缺乏芳香性。
• Facile formation of acenaphtho[1,2-a]pyrene structures by thermal isomerization of bis(8-ethynyl-1-naphthyl)ethynes
  作者：Shinji Toyota、Keiko Kaneko、Megumi Kurokawa、Kan Wakamatsu

  DOI：10.1016/j.tetlet.2006.08.011

  日期：2006.10

  1,8-naphthylene–ethynylene compounds underwent thermal isomerization into acenaphtho[1,2-a]pyrene derivatives, and the structure of the new polycyclic aromatic system was established by X-ray analysis. The mechanism of the isomerization is explained in terms of sequential cyclization reactions via biradical intermediates followed by hydrogen migration.

  将标题的1,8-萘-乙炔化合物进行热异构化为[1,2- a ] py衍生物，并通过X射线分析建立了新的多环芳族体系的结构。异构化的机理通过依次通过双自由基中间体进行环化反应以及随后的氢迁移来解释。
• Tetradehydrodinaphtho[10]annulene: A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives
  作者：Rui Umeda、Daijiro Hibi、Koji Miki、Yoshito Tobe

  DOI：10.1021/ol9015942

  日期：2009.9.17

  The synthesis and structural characterization of hitherto unknown tetradehydrodinaphtho[10]annulene, a hydrocarbon whose synthesis had been attempted four decades ago, was achieved for the first time. Moreover, the dinaphtho[10]annulene was transformed smoothly into stable zethrene derivatives substituted at its 7,14-positions, showing that it serves as a good reservoir of zethrene derivatives. Optical

  首次实现了迄今未知的四氢二萘并[10]环戊烯的合成和结构表征，该烃是四十年前尝试合成的。此外，二萘并[10]环戊烯被平稳地转化为稳定的茂烃衍生物，该衍生物在其7,14位被取代，表明它可以作为茂烃衍生物的良好储库。还显示了二取代的蒽衍生物的光学和电化学性质。
• Synthesis of a chiral binaphthyldisulfide: A potentially useful reagent for catalytic asymmetric synthesis
  作者：Ken S. Feldman、Robert E. Ruckle、Susan M. Ensel、Paul H. Weinreb

  DOI：10.1016/s0040-4039(00)60846-8

  日期：1992.11

  Diels Alder cycloaddition/oxygen-atom-extrusion provides the means to unite two naphthylene fragments and affords a highly functionalized, racemic binaphthyl iodide. Resolution of a derived thiol then furnishes, after appropriate manipulation, enantiomerically pure binaphthyldisulfide precatalysts.