1-iodo-5,10-dodecadiyne | 150584-24-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-iodo-5,10-dodecadiyne
• 英文别名: 12-Iodododeca-2,7-diyne
• CAS: 150584-24-0
• 化学式: C₁₂H₁₇I
• 分子量: 288.171
• InChiKey: WVWYAENBRXCSTC-UHFFFAOYSA-N

物化性质

• 沸点：
  312.5±22.0 °C(predicted)
• 密度：
  1.358±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-5,10-dodecadiyne 在 叔丁基锂 作用下， 生成 Dodeca-2,7-diyne 、 2-Eth-(E)-ylidene-bicyclopentylidene 、 Hept-5-ynylidene-cyclopentane
  参考文献：
  名称：

  Tandem Cyclization of Enynyl and Diynyl Alkyllithiums

  摘要：

  Undec-10-en-5-ynyllithium由相应的碘化物通过低温锂-碘交换生成，当升温至室温时，经历两次连续的5-外向环化，以85%的产率生成2-甲基-1-环戊烯基环戊烷。类似二乙炔烷基锂的串联环化尝试不太成功。

  DOI：

  10.1246/cl.1993.819
• 作为产物：
  描述：

  己-4-炔-1-醇 在 氢氧化钾 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 67.67h， 生成 1-iodo-5,10-dodecadiyne
  参考文献：
  名称：

  Three-Component Intramolecular Two-Alkyne Annulations of Fischer Carbene Complexes: New Strategies for Steroid Synthesis

  摘要：

  The two-alkyne annulations of a variety of chromium and tungsten carbene complexes are examined in which both of the alkynes are tethered to the carbene complex. The reactions of complexes in which the two alkynes and the first alkyne and the carbene carbon are connected by methylene groups were investigated for their potential in the construction of tricyclic phenols. This methodology was screened for a number of different ring sizes, and it was found that the efficiency of phenol formation depended on the nature of the metal, the solvent, and the sizes of the rings produced. In the reactions of chromium complexes, for certain ring sizes an unprecedented lactone product was also observed which resulted from the incorporation of the two alkynes as well as two carbon monoxide ligands from the metal. A new strategy for entry to the tetracyclic ring system of steroids is developed that involves a tandem coupling of a Diels-Alder reaction of carbene complexes with the double-intramolecular two-alkyne annulation. In a model system where the A and C rings are aromatic, the feasibility of this strategy was demonstrated in a reaction where all four rings of the steroid ring system can be generated in a one-pot reaction. In a second generation of this strategy, it was demonstrated that the tandem coupling of these reactions can also lead to the generation of nonaromatic steroidal ring systems.

  DOI：

  10.1021/ja00096a019

文献信息

• Three-Component Intramolecular Two-Alkyne Annulations of Fischer Carbene Complexes: New Strategies for Steroid Synthesis
  作者：Jianming Bao、William D. Wulff、Vera Dragisich、Steve Wenglowsky、Richard G. Ball

  DOI：10.1021/ja00096a019

  日期：1994.8

  The two-alkyne annulations of a variety of chromium and tungsten carbene complexes are examined in which both of the alkynes are tethered to the carbene complex. The reactions of complexes in which the two alkynes and the first alkyne and the carbene carbon are connected by methylene groups were investigated for their potential in the construction of tricyclic phenols. This methodology was screened for a number of different ring sizes, and it was found that the efficiency of phenol formation depended on the nature of the metal, the solvent, and the sizes of the rings produced. In the reactions of chromium complexes, for certain ring sizes an unprecedented lactone product was also observed which resulted from the incorporation of the two alkynes as well as two carbon monoxide ligands from the metal. A new strategy for entry to the tetracyclic ring system of steroids is developed that involves a tandem coupling of a Diels-Alder reaction of carbene complexes with the double-intramolecular two-alkyne annulation. In a model system where the A and C rings are aromatic, the feasibility of this strategy was demonstrated in a reaction where all four rings of the steroid ring system can be generated in a one-pot reaction. In a second generation of this strategy, it was demonstrated that the tandem coupling of these reactions can also lead to the generation of nonaromatic steroidal ring systems.
• Tandem Cyclization of Enynyl and Diynyl Alkyllithiums
  作者：William F. Bailey、Timo V. Ovaska

  DOI：10.1246/cl.1993.819

  日期：1993.5

  Undec-10-en-5-ynyllithium, generated from the corresponding iodide by low-temperature lithium – iodine exchange, undergoes two sequential 5-exo cyclizations when warmed to room temperature to afford 2-methyl-1-cyclopentylidenecyclopentane in 85% yield. Attempted tandem cyclization of an analogous diacetylenic alkyllithium was less successful.

  Undec-10-en-5-ynyllithium由相应的碘化物通过低温锂-碘交换生成，当升温至室温时，经历两次连续的5-外向环化，以85%的产率生成2-甲基-1-环戊烯基环戊烷。类似二乙炔烷基锂的串联环化尝试不太成功。