(16E,19E)-6,7,9,10-tetrahydro-18H-dibenzo[h,o][1,4,7]trioxacyclohexadecin-18-one | 137794-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (16E,19E)-6,7,9,10-tetrahydro-18H-dibenzo[h,o][1,4,7]trioxacyclohexadecin-18-one
• 英文别名: 8,9:15,16-dibenzo-1,4,7-trioxacyclohexadeca-8,10,13,15-tetraen-12-one；(2E,5E)-13,16,19-trioxatricyclo[18.4.0.07,12]tetracosa-1(24),2,5,7,9,11,20,22-octaen-4-one
• CAS: 137794-15-1
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: OAUQJWFQPWDOSF-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (16E,19E)-6,7,9,10-tetrahydro-18H-dibenzo[h,o][1,4,7]trioxacyclohexadecin-18-one 在 镍 氢气 、 sodium ethanolate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 20.0h， 生成 2''-hydroxy-5''-nitro-8,9:11,13:15,16-tribenzo-1,4,7-trioxacyclohexadeca-8,11,15-triene
  参考文献：
  名称：

  New crown ether-like macrocycles containing a nitrophenol unit. Synthesis and metal ion effects on the reactivity of their acetates in transacylation reactions

  摘要：

  A series of crown ether-like macrocyclic compounds 3 containing the 2,6-dibenzyl-4-nitrophenol substructure have been prepared by cyclization reactions of disalicylideneacetone 4 with ditosylates 7 of oligoethylene glycols, followed by hydrogenation and double aldol condensation with nitromalondialdehyde. These compounds may be regarded as possessing a section of a 1,3-crowned calix[4]arene. X-ray analysis of two examples shows, however, that the three phenolic units linked via o-methylene groups adopt a conformation different to the all-cis conformation found in calix[4]arenes. The reaction of the nitrophenyl acetates derived from 3 and from suitable model compounds with ethoxide in ethanol was studied kinetically. This reaction is accelerated by the addition of SrBr2 and BaBr2 in all cases, indicating that the metal ion is bound more strongly to the transition state than to the initial state. Especially high acceleration factors (up to 700 in the case of 10e) were observed for cyclic and open-chain compounds with longer flexible oligoethylene oxide chains, which means that only in these cases do the ether oxygens contribute effectively to the binding of the metal ion in the transition state.

  DOI：

  10.1021/jo00029a009
• 作为产物：
  描述：

  1,5-bis(benzaldehydeoxy)-3-oxopentane 、 丙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.5h， 以38%的产率得到(16E,19E)-6,7,9,10-tetrahydro-18H-dibenzo[h,o][1,4,7]trioxacyclohexadecin-18-one
  参考文献：
  名称：

  单晶中二亚芳基丙酮基冠磷的预组织光化学转化

  摘要：

  使用模拟分子晶体堆积的方法，在X射线衍射数据的基础上，研究了晶体堆积的具体特征和二亚芳基丙酮基冠甲烷分子向固相光化学转化的预组织。揭示了大部分合成的大环 E,E-异构体形成同手性晶体 (P212121) 的趋势，而 (23E,26E)-11,12,14,15-四氢-8H-二萘酚-[2 ,1-k:1',2'-r][1,4,7,10]tetraoxacyclononadecine-23,26-dien-25(9H)-one 容易发生多态性。对于这种冠纸的一种改性，发现了一种分子固相立体有择光化学二聚化现象，该现象根据同步头尾型分子进行，而没有晶体破坏（单晶-单晶转变）。

  DOI：

  10.1007/s11172-011-0131-x

文献信息

• Synthesis of crownophane with the bicyclo[2.2.2]octane core
  作者：I. G. Ovchinnikova、E. G. Matochkina、M. I. Kodess、P. A. Slepukhin、O. V. Fedorova、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-011-0161-4

  日期：2011.5