<16>Orthocyclophane-1,3-dione | 152897-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <16>Orthocyclophane-1,3-dione
• 英文别名: <1₆>Orthocyclophane-1,3-dione
• CAS: 152897-35-3
• 化学式: C₄₂H₃₂O₂
• 分子量: 568.715
• InChiKey: YZGXMABSTVMMRK-UHFFFAOYSA-N

物化性质

• 沸点：
  760.6±60.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  44.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <16>Orthocyclophane-1,3-dione 在 lithium aluminium tetrahydride 、 titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到Nonacyclo<27.13.0.0^2,7.0^9,14.0^16,21.0^23,28.0^30,35.0^37,42>ditetraconta-1(29),2(7),3,5,9(14),10,12,16(21),17,19,23(28),24,26,30(35),31,33,37(42)38,40-nonadecaene
  参考文献：
  名称：

  Orthocyclophanes. 2. Starands, a new family of macrocycles of spirobicyclic polyketals with a 2n-crown-n moiety

  摘要：

  Synthesis and functionalization of higher members of the [1n]orthocyclophanes, or [1n]OCPs, have been investigated. Oxidation of the benzylic methylenes in [1n]OCPs gave the polyoxo derivatives. Exhaustive oxidation of all methylenes in even-numbered [1n]OCPs gave rearranged isomers of the cyclopolyketal structure instead of the corresponding polyoxo derivatives. We propose the class name ''starands'' for this new family of crown compounds for their star-shaped crown ether structure. Detailed synthesis and characterization of two starands are described.

  DOI：

  10.1021/jo00077a044
• 作为产物：
  描述：

  Bis<2-<2(hydroxymethyl)benzyl>phenyl>methane ditetrahydropyran-2-yl ether 在 正丁基锂 、 Celite 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 <16>Orthocyclophane-1,3-dione
  参考文献：
  名称：

  Orthocyclophanes. 2. Starands, a new family of macrocycles of spirobicyclic polyketals with a 2n-crown-n moiety

  摘要：

  Synthesis and functionalization of higher members of the [1n]orthocyclophanes, or [1n]OCPs, have been investigated. Oxidation of the benzylic methylenes in [1n]OCPs gave the polyoxo derivatives. Exhaustive oxidation of all methylenes in even-numbered [1n]OCPs gave rearranged isomers of the cyclopolyketal structure instead of the corresponding polyoxo derivatives. We propose the class name ''starands'' for this new family of crown compounds for their star-shaped crown ether structure. Detailed synthesis and characterization of two starands are described.

  DOI：

  10.1021/jo00077a044