1-iodo-2-[(trimethylsilyl)ethynyl]biphenylene | 144192-97-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-iodo-2-[(trimethylsilyl)ethynyl]biphenylene
• 英文别名: [(1-Iodobiphenylen-2-yl)ethynyl](trimethyl)silane；2-(1-iodobiphenylen-2-yl)ethynyl-trimethylsilane
• CAS: 144192-97-2
• 化学式: C₁₇H₁₅ISi
• 分子量: 374.296
• InChiKey: VQUWWJRDDZEOOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-2-[(trimethylsilyl)ethynyl]biphenylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 2-ethynyl-1-[2-(2-ethynylbiphenylen-1-yl)ethynyl]biphenylene
  参考文献：
  名称：

  The total synthesis of angular [4]- and [5]phenylene

  摘要：

  DOI：

  10.1021/ja00050a091
• 作为产物：
  描述：

  1-[dimethyl(thexyl)silyl]-2-(trimethylsilyl)biphenylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-iodo-2-[(trimethylsilyl)ethynyl]biphenylene
  参考文献：
  名称：

  (η6-[7]Heliphene)tricarbonylchromium via an Optimized Preparation of [7]Heliphene

  摘要：

  Optimized procedures to [7]heliphene are described that allowed the synthesis of ((6)-[7]heliphene)tricarbonylchromium and a preliminary exploration of its chemical behavior. DFT calculations provide structural and energetic information on this complex and its haptomeric isomers. Attempts to prepare the corresponding ([7]heliphene)chromium sandwich failed so far, but DFT evidence is presented to indicate that the target should be accessible.

  DOI：

  10.1055/s-0034-1380535

文献信息

• Cobalt-Mediated Synthesis of Angular [4]Phenylene:  Structural Characterization of a Metallacyclopentadiene(Alkyne) Intermediate and Its Thermal and Photochemical Conversion
  作者：Peter I. Dosa、Glenn D. Whitener、K. Peter C. Vollhardt、Andrew D. Bond、Simon J. Teat

  DOI：10.1021/ol025956o

  日期：2002.6.1

  metallacyclopentadiene(alkyne) complex has been obtained. This type of metallacycle is believed to be the key intermediate in the cobalt-mediated [2 + 2 + 2]cycloaddition of alkynes. Thermal treatment leads to the generation of angular [4]phenylene, the X-ray structural details of which are described. Under photochemical conditions, the cobaltacycle isomerizes to a highly strained (cyclobutadieno)dibenzocyclooctatrienyne

  [反应：见正文]已获得单核金属环戊二烯（炔）配合物的第一个X射线晶体结构。据信这种金属环化合物是炔烃在钴介导的[2 + 2 + 2]环加成反应中的关键中间体。热处理导致生成角[4]亚苯基，对X射线的结构细节进行了描述。在光化学条件下，钴环异构化为高度紧张的（环丁二烯）二苯并环辛三烯复合物。
• (η6-[7]Heliphene)tricarbonylchromium via an Optimized Preparation of [7]Heliphene
  作者：K. Vollhardt、Daniel Holmes、Sang Lee、Sabine Lotz、Son Nguyen、Gaston Schaller、Rachel Schmidt-Radde

  DOI：10.1055/s-0034-1380535

  日期：——

  Optimized procedures to [7]heliphene are described that allowed the synthesis of ((6)-[7]heliphene)tricarbonylchromium and a preliminary exploration of its chemical behavior. DFT calculations provide structural and energetic information on this complex and its haptomeric isomers. Attempts to prepare the corresponding ([7]heliphene)chromium sandwich failed so far, but DFT evidence is presented to indicate that the target should be accessible.
• The total synthesis of angular [4]- and [5]phenylene
  作者：Rachel H. Schmidt-Radde、K. Peter C. Vollhardt

  DOI：10.1021/ja00050a091

  日期：1992.11