oxacyclooctadeca-11,13-diyn-2-one | 1346556-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: oxacyclooctadeca-11,13-diyn-2-one
• CAS: 1346556-89-5
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: CDAOLFKGJFWBRA-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±34.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  hex-5-yn-1-yl undec-10-ynoate 在 吡啶 、 氧气 、 三乙胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 甲醇 为溶剂， 以74%的产率得到oxacyclooctadeca-11,13-diyn-2-one
  参考文献：
  名称：

  Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings

  摘要：

  Macrocycles are abundant in numerous chemical applications, however the traditional strategy for the preparation of these compounds remains cumbersome and environmentally damaging; involving tedious reaction set-ups and extremely dilute reaction media. The development of a macrocyclization strategy conducted at high concentrations is described which exploits phase separation of the catalyst and substrate, as a strategy to control dilution effects. Sequestering a copper catalyst in a highly polar and/or hydrophilic phase can be achieved using a hydrophilic ligand, T-PEG(1900), a PEGylated TMEDA derivative. Similarly, phase separation is possible when suitable copper complexes are soluble in PEG(400), a green and efficient solvent which can be utilized in biphasic mixtures for promoting macrocyclization at high concentrations. The latter phase separation technique can be exploited for the synthesis of a wide range of industrially relevant macrocycles with varying ring sizes and functional groups.

  DOI：

  10.1021/ja208902t

文献信息

• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
  作者：Guillaume Force、Anna Perfetto、Robert J. Mayer、Ilaria Ciofini、David Lebœuf

  DOI：10.1002/anie.202105882

  日期：2021.9

  towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables

  大环内酯是一类特殊的天然和合成产品，在精细化学品和制药行业有着广泛的应用。尽管在合成方面取得了所有进展，特别是从seco-酸，一种有效的、选择性的、灵活的、容易获得的并且尽可能与多种官能团相容的大环内酯化促进剂系统仍然缺乏。在这里，我们描述了一种策略，该策略依赖于形成包含五氟苯基的混合酸酐，由于其高电子活化，可以方便地获得具有广泛多功能性的大环内酯、大二内酯和酯。进行动力学研究和 DFT 计算以合理化五氟苯基在大环内酯化反应中的反应性。