1,6,13,18-tetraoxa-cyclotetracosane-2,5,14,17-tetraone | 141850-18-2

• 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: 1,6,13,18-tetraoxa-cyclotetracosane-2,5,14,17-tetraone
• 英文别名: 1,6,13,18-Tetraoxa-cyclotetracosan-2,5,14,17-tetraon；1,6,13,18-Tetraoxacyclotetracosane-2,5,14,17-tetrone
• CAS: 141850-18-2
• 化学式: C₂₀H₃₂O₈
• 分子量: 400.469
• InChiKey: XILZQFDAUSKCSV-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  706.2±60.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-((6-碘己基)氧基)-4-氧代丁酸 在 silver tetrafluoroborate 、 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 84.0h， 生成 1,6,13,18-tetraoxa-cyclotetracosane-2,5,14,17-tetraone
  参考文献：
  名称：

  Synthesis of macrocyclic dilactones by cyclization of sulfonium salts

  摘要：

  An efficient method for the formation of macrocyclic dilactones via cyclization of (omega-carboxyalkyl)diphenylsulfonium salts 3 containing an ester linkage under mild conditions is described. These sulfonium salts 3 were cyclized in the presence of cesium carbonate under high-dilution conditions to give 11- to 16-membered dilactones 4 in good yields. The cyclization of sulfonium salt 22 was successfully carried out for the synthesis of 11-membered dilactonic pyrrolizidine alkaloid, 13,13-dimethyl-1,2-didehydrocrotalanine 23.

  DOI：

  10.1021/jo00040a013

文献信息

• Synthesis of Macrocyclic Dilactones through Lipases
  作者：Mª Pilar Bosch、Angel Guerrero

  DOI：10.1055/s-2005-917099

  日期：——

  We report herein a selective and efficient method to prepare macrocyclic dilactones in good yields from diols and succinic anhydride through a biocatalytic condensation reaction.

  我们在此报告了一种通过生物催化缩合反应从二醇和琥珀酸酐以良好收率制备大环双内酯的选择性和有效方法。
• Meta and Para Rings¹
  作者：E. W. Spanagel、Wallace H. Carothers

  DOI：10.1021/ja01308a047

  日期：1935.5
• Synthesis of macrocyclic dilactones by cyclization of sulfonium salts
  作者：Takako Nakamura、Haruo Matsuyama、Nobumasa Kamigata、Masahiko Iyoda

  DOI：10.1021/jo00040a013

  日期：1992.7

  An efficient method for the formation of macrocyclic dilactones via cyclization of (omega-carboxyalkyl)diphenylsulfonium salts 3 containing an ester linkage under mild conditions is described. These sulfonium salts 3 were cyclized in the presence of cesium carbonate under high-dilution conditions to give 11- to 16-membered dilactones 4 in good yields. The cyclization of sulfonium salt 22 was successfully carried out for the synthesis of 11-membered dilactonic pyrrolizidine alkaloid, 13,13-dimethyl-1,2-didehydrocrotalanine 23.