1-hex-4-ynl triflate | 85355-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-hex-4-ynl triflate
• 英文别名: 4-Hexynyl triflate；Hex-4-ynyl trifluoromethanesulfonate
• CAS: 85355-20-0
• 化学式: C₇H₉F₃O₃S
• 分子量: 230.208
• InChiKey: JYWHYQBESSIQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-hex-4-ynl triflate 在 氢氧化钾 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 61.67h， 生成
  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
• 作为产物：
  描述：

  己-4-炔-1-醇 、 三氟甲磺酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-hex-4-ynl triflate
  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

• Synthesis and reactivity of alkynyloxy molybdenum carbene complexes: formation of cyclopropyl substituted dihydrofurans and dihydropyrans
  作者：Daniel F. Harvey、Matthew F. Brown

  DOI：10.1016/s0040-4039(00)92349-9

  日期：1991.9

  Alkynyloxycarbene complexes of molybdenum have been found to readily cyclize to give cyclopropyldihydrofurans and cyclopropyldihydropyrans upon thermolysis in the presence of methyl acrylate.

  已经发现钼的炔基氧卡宾络合物在丙烯酸甲酯存在下热解时容易环化以产生环丙基二氢呋喃和环丙基二氢吡喃。