1,3-diiodo-3-butene | 142389-41-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,3-diiodo-3-butene
• 英文别名: 2,4-Diiodobut-1-ene
• CAS: 142389-41-1
• 化学式: C₄H₆I₂
• 分子量: 307.901
• InChiKey: DPYXOVCCBDDYJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-allyl-phenylamine 、 1,3-diiodo-3-butene 以 水 为溶剂， 以65%的产率得到2-Allyl-N-(3-iodo-3-butenyl)aniline
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles

  摘要：

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.

  DOI：

  10.1002/chem.19970030820
• 作为产物：
  描述：

  3-iodo-3-butenyl methanesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 1,3-diiodo-3-butene
  参考文献：
  名称：

  通过钯催化的1,2-二烯杂环环化反应合成中环氮杂环。

  摘要：

  七，八和九元环氮杂环很容易通过钯催化的各种1,2-二烯的杂芳环化反应，通过一系列含甲苯磺酰胺和胺的芳基和乙烯基卤化物来制备。形成环的难易程度是7> 8> 9，使用芳基卤化物而不是乙烯基卤化物和甲苯磺酰胺官能团而不是胺官能团可获得更好的结果。建议该反应通过将芳基或乙烯基钯化合物形成并添加到丙二烯中以产生π-烯丙基钯中间体而进行，该中间体随后在π-烯丙基系统的受阻较小的末端进行钯的亲核置换。

  DOI：

  10.1021/jo980516p

文献信息

• A Synthesis of Echinopine B
  作者：Theo D. Michels、Matthew S. Dowling、Christopher D. Vanderwal

  DOI：10.1002/anie.201203147

  日期：2012.7.23

  In a short synthesis of echinopine B, a guaiane‐like intermediate was generated through a methylenecyclopentane annulation onto a substituted cycloheptenone. The resulting bicyclic compound was converted into the natural product by a PtCl2‐catalyzed enyne cycloisomerization (see scheme). Several late‐stage polycyclic rearrangement products were isolated and characterized.

  在棘手类松果碱B的短合成中，通过亚甲基环戊烷环合到取代的环庚烯酮上生成了愈创树状中间体。所得的双环化合物通过PtCl 2催化的烯炔环异构化转化为天然产物（参见方案）。分离并鉴定了几种晚期多环重排产物。
• Nickel-Catalyzed Enantioselective Pyridone C–H Functionalizations Enabled by a Bulky <i>N-</i>Heterocyclic Carbene Ligand
  作者：Johannes Diesel、Anastasiia M. Finogenova、Nicolai Cramer

  DOI：10.1021/jacs.8b01181

  日期：2018.4.4

  Annulated pyridones are an important scaffold found in many biologically active compounds. A Ni(0)-catalyzed C-H functionalization of 2- and 4-pyridones is disclosed, providing access to annulated pyridones via enantioselective intramolecular olefin hydroarylation. Key to the success of the transformation was the development of a sterically hindered and tunable N-heterocyclic carbene ligand resembling a chiral version of IPr. This ligand allows for mild reaction temperatures, and leads to the annulated pyridones in excellent yields and enantioselectivities.
• A catalytic asymmetric synthesis of hydrindans
  作者：Yoshihiro Sato、Takahiro Honda、Masakatsu Shibasaki

  DOI：10.1016/s0040-4039(00)92252-4

  日期：1992.4

  The cis-hydrindan derivative 14b has been synthesized in up to 86% ee by an asymmetric Heck reaction starting with the prochiral alkenyl iodide 9b or the alkenyl triflate 13.
• Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1002/chem.19970030820

  日期：1997.8

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.
• Synthesis of Medium-Ring Nitrogen Heterocycles via Palladium-Catalyzed Heteroannulation of 1,2-Dienes
  作者：Richard C. Larock、Chi Tu、Paola Pace

  DOI：10.1021/jo980516p

  日期：1998.10.1

  nitrogen heterocycles are readily prepared by the palladium-catalyzed heteroannulation of a variety of 1,2-dienes by a range of tosylamide- and amine-containing aryl and vinylic halides. The ease of ring formation is seven > eight > nine, and better results are obtained using aryl halides, rather than vinylic halides, and tosylamide functionality, rather than amine functionality. The reaction is suggested

  七，八和九元环氮杂环很容易通过钯催化的各种1,2-二烯的杂芳环化反应，通过一系列含甲苯磺酰胺和胺的芳基和乙烯基卤化物来制备。形成环的难易程度是7> 8> 9，使用芳基卤化物而不是乙烯基卤化物和甲苯磺酰胺官能团而不是胺官能团可获得更好的结果。建议该反应通过将芳基或乙烯基钯化合物形成并添加到丙二烯中以产生π-烯丙基钯中间体而进行，该中间体随后在π-烯丙基系统的受阻较小的末端进行钯的亲核置换。