spiro[cyclohexane-1,4'-3',5'-dioxa-8',10'-dichlorobicyclo[2.2.0]hexa-8',10'-diene]

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: spiro[cyclohexane-1,4'-3',5'-dioxa-8',10'-dichlorobicyclo[2.2.0]hexa-8',10'-diene]
• 英文别名: (1S,7S)-8,10-dichlorospiro[3,5-dioxatricyclo[5.2.2.01,7]undeca-8,10-diene-4,1'-cyclohexane]
• 化学式: C₁₄H₁₆Cl₂O₂
• 分子量: 287.186
• InChiKey: AYCUREAIOWHFNL-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro[cyclohexane-1,4'-3',5'-dioxa-8',10'-dichlorobicyclo[2.2.0]hexa-8',10'-diene] 在 四(三苯基膦)钯 吡啶 、 copper(l) iodide 、 copper diacetate 、 四丁基氟化铵 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  [46]对环十二烷衍生物的合成与表征

  摘要：

  [46] 具有新型带状完全共轭 π 系统的对环芳十二烷衍生物 1 是由相应的六（杜瓦苯）前体 7 作为高应变但可分离的化合物光化学生成的。

  DOI：

  10.1039/b108253c
• 作为产物：
  描述：

  (2,3,5,6-Tetrachloro-4-hydroxymethyl-bicyclo[2.2.0]hex-1-yl)-methanol 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 spiro[cyclohexane-1,4'-3',5'-dioxa-8',10'-dichlorobicyclo[2.2.0]hexa-8',10'-diene]
  参考文献：
  名称：

  Syntheses of Acetylenic Oligophenylene Macrocycles Based on a Novel Dewar Benzene Building Block Approach

  摘要：

  A general synthetic approach to strained p-phenylene-based acetylenic macrocycles is described. A key feature in this approach is exploitation of Dewar benzene as an angular p-phenylene synthon. Thus, 1,4-acetal-bridged 2,5-dichloro(Dewar benzene) 5, prepared in four steps from dimethyl acetylenedicarboxylate and 1,2-dichloroethylene, is applied as such a building block in the syntheses of strained macrocycles 13 and anti-20. For the synthesis of 13, m-phenylene units are used as spacers and modified Eglington-Glaser coupling is applied for the macrocyclization step. For the synthesis of anti-20, on the other hand, o-phenylene units are used as spacers and Sonogashira coupling is applied for the macrocyclization step. Macrocycles 13 and anti-20 are characterized crystallographically? and their strained nature is reflected mainly in the deviation of the acetylene units from linearity; the C=C-C angles range from 168.7(3)degrees to 179.9(3)degrees in 13 and from 168.0(5)degrees to 171.4(4)degrees in anti-20, Macrocycle 13 shows unique conformational property, namely, the p-phenylene units arranged in parallel in the rectangular framework rotate freely about the long axes, as evidenced by the H-1 NMR studies. Macrocycle anti-20 exhibits a Stokes shift of 179 nm, which is exceptionally large for phenylacetylene macrocycles, presumably owing to the characteristic stacking structure.

  DOI：

  10.1021/jo0002590

文献信息

• First Dewar benzene approach to acetylenic oligophenylene macrocycles: synthesis and structure of a molecular rectangle bearing two spindles
  作者：Masakazu Ohkita、Kohta Ando、Ken-ichi Yamamoto、Takanori Suzuki、Takashi Tsuji

  DOI：10.1039/a908711g

  日期：——

  A novel Dewar benzene approach to the construction of oligophenylene macrocycles has been developed by introducing Dewar benzene 1 as a building block and applied to the synthesis of a molecular rectangle 8, whose structure was characterized crystallographically.

  一种新颖的杜瓦苯方法用于构建寡苯基大环，该方法通过引入杜瓦苯 1 作为构建模块，并应用于分子矩形 8 的合成，其结构通过晶体学方法进行了表征。