4-(2-iodophenoxy)-but-2-ynal diethyl acetal | 457865-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-iodophenoxy)-but-2-ynal diethyl acetal
• 英文别名: 1-(4,4-diethoxybut-2-ynyloxy)-2-iodobenzene；1-(4,4-Diethoxybut-2-ynoxy)-2-iodobenzene
• CAS: 457865-52-0
• 化学式: C₁₄H₁₇IO₃
• 分子量: 360.192
• InChiKey: DBVPJJYQYSTGRG-UHFFFAOYSA-N

物化性质

• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-iodophenoxy)-but-2-ynal diethyl acetal 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 3-(2-ethoxy-vinyl)benzofuran
  参考文献：
  名称：

  New Carbanionic Access to 3-Vinylindoles and 3-Vinylbenzofurans

  摘要：

  [GRAPHICS]A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.

  DOI：

  10.1021/ol026351v
• 作为产物：
  描述：

  二乙基苯基甲烷 在 偶氮二甲酸二异丙酯 、 乙基溴化镁 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 生成 4-(2-iodophenoxy)-but-2-ynal diethyl acetal
  参考文献：
  名称：

  New Carbanionic Access to 3-Vinylindoles and 3-Vinylbenzofurans

  摘要：

  [GRAPHICS]A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.

  DOI：

  10.1021/ol026351v

文献信息

• Synthetic Applications of the Nickel-Catalyzed Cyclization of Alkynes Combined with Addition Reactions in a Domino Process
  作者：Muriel Durandetti、Lucie Hardou、Rudy Lhermet、Mathieu Rouen、Jacques Maddaluno

  DOI：10.1002/chem.201100967

  日期：2011.11.4

  Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel‐catalyzed domino cyclization–condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo‐dig cyclization. This convenient and mild method constitutes a one‐pot synthesis of substituted dihydrobenzofurans

  炔烃的羰基化和所得乙烯基镍部分的官能化已在镍催化的多米诺环化-缩合过程中有效地进行。该反应不需要制备任何其他有机金属试剂，仅通过exo- dig环化即可进行。这种方便，温和的方法构成了取代的二氢苯并呋喃，苯并二氢吡喃，异苯并二氢吡喃，吲哚或茚满的单锅合成。这些有价值的产物通常以高收率和高立体选择性获得。它们被证明是有用的合成子，可用于快速进入功能化的多环骨架。
• Heterocyclization by catalytic carbonickelation of alkynes: a domino sequence involving vinylnickels
  作者：Muriel Durandetti、Lucie Hardou、Marie Clément、Jacques Maddaluno

  DOI：10.1039/b902095k

  日期：——

  Reaction of Ni(0) in the presence of iodoarylethers 1 leads, after syn intramolecular carbonickelation of the triple bond, to nucleophilic vinylnickels which can be trapped, in a tandem process, by various electrophiles introduced at the onset of the reaction.

  在碘芳醚1存在下，Ni(0)的反应经过三键的对称分子内碳镍化，导致亲核乙烯镍的生成，这些亲核乙烯镍可以在反应开始时通过引入各种电亲体进行捕获，形成串联反应。