syn-11-carboxy-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene | 166582-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: syn-11-carboxy-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene
• CAS: 166582-39-4
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: FUIHIMHWCSXOLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  syn-11-carboxy-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 5.5h， 生成 3-(3-Propoxy-phenyl)-bicyclo[4.4.1]undeca-1(10),2,4,6,8-pentaene-11-carbonyl chloride
  参考文献：
  名称：

  Effects of Amphiphilic Topology on Self-Association in Solution, at the Air-Water Interface, and in the Solid State

  摘要：

  The self-association of sodium carboxylates 1a-5a in aqueous solution has been studied by H-1 NMR and dye solubilization. Amphiphile 1a, the derivative of 1,6-methano[10]annulene bearing a carboxylate on the bridge carbon, is an example of a ''contrafacial amphiphile'', a rigid molecule with distinct polar and nonpolar faces. Amphiphiles 2a and 3a, the sodium salts of 2-naphthylacetic and 1-naphthylacetic acids, respectively, are isomers of la with more conventional amphiphilic architectures. Amphiphiles 4a and 5a are derivatives of 1a with extended nonpolar surfaces. Concentration-dependent H-1 NMR data indicate that self-association of 1a-5a is weak and occurs in a stepwise fashion. Up to its aqueous solubility limit of 0.54 M, contrafacial amphiphile la does not solubilize the hydrophobic dye orange OT, but conventional isomers 2a and 3a solubilize the dye above 0.33 and 0.50 M, respectively. Contrafacial amphiphile 4a also does not solubilize orange OT, but 5a does solubilize the dye. The properties of isomers 1a-3a were compared also at the air-water interface. via tensiometry. Between zero and 0.15 M, naphthyl derivatives 2a and 3a cause a significant lowering of surface tension, but contrafacial amphiphile la has little effect on surface tension up to 0.35 M. Crystal structures of carboxylic acids 1b, 4b, and 5b show that the aromatic face of the 1,6-methano[10]annulene unit that is anti to the bridge engages in ''herringbone'' interactions with neighboring aromatic surfaces, which is similar to the behavior of conventional hydrocarbon aromatic moieties. The solid state packing patterns observed for 1b-3b allow a speculative rationalization of the differences in surface activity among 1a-3a.

  DOI：

  10.1021/ja00122a017
• 作为产物：
  描述：

  allyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)<4.4.1>propella-2,8-diene-11-carboxylate 在 吗啉 、 potassium fluoride 、 四(三苯基膦)钯 、 氢溴酸 、 caesium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 129.75h， 生成 syn-11-carboxy-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene
  参考文献：
  名称：

  Synthetic Studies on the 1,6-Methano[10]annulene Skeleton: A New Route That Provides Derivatives Substituted at the Bridge and on the Annulene Ring

  摘要：

  A new synthetic route to the 1,6-methano[10]annulene skeleton has been developed. The key step in this route is the semi-benzylic Favorskii rearrangement of a [4.4.2]propellane to a [4.4.1]propellane. The methodology discussed here provides access to 1,6-methano[10]annulene derivatives bearing substituents on both the bridge carbon and the annulene ring. Control of the relative positioning of these appendages is achieved by introducing the annulene substituent via cuprate addition to an allylic lactone.

  DOI：

  10.1021/ja00102a020