(2,3,5,6-Tetrachloro-4-hydroxymethyl-bicyclo[2.2.0]hex-1-yl)-methanol | 130208-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,5,6-Tetrachloro-4-hydroxymethyl-bicyclo[2.2.0]hex-1-yl)-methanol
• CAS: 130208-47-8
• 化学式: C₈H₁₀Cl₄O₂
• 分子量: 279.978
• InChiKey: OJNYZOPYRHYJHE-AMPFEYJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2,3,5,6-Tetrachloro-4-hydroxymethyl-bicyclo[2.2.0]hex-1-yl)-methanol 在 disodium-phenanthrene 、 对甲苯磺酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 苯 为溶剂， 生成 ((1s,4s)-bicyclo[2.2.0]hexa-2,5-diene-1,4-diyl)dimethanol
  参考文献：
  名称：

  Convenient Synthesis of Some Functionalized Dewar Benzenes and Effect of Chlorine Substitution on the Rates of Their Aromatization

  摘要：

  以约10%的总收率，从二甲基乙炔二羧酸酯出发，通过五步骤合成了1,4-双（羟甲基）DeWar苯，并测定了其芳构化速率：在2,5-和2,6-位置上同时进行二氯取代，显著减缓了异构化过程。

  DOI：

  10.1246/cl.1990.1193
• 作为产物：
  描述：

  1,3-bis(methoxycarbonyl)-2,3,5,6-tetrachlorobicyclo[2.2.0]hexane 在 lithium aluminium tetrahydride 作用下， 生成 (2,3,5,6-Tetrachloro-4-hydroxymethyl-bicyclo[2.2.0]hex-1-yl)-methanol
  参考文献：
  名称：

  Convenient Synthesis of Some Functionalized Dewar Benzenes and Effect of Chlorine Substitution on the Rates of Their Aromatization

  摘要：

  以约10%的总收率，从二甲基乙炔二羧酸酯出发，通过五步骤合成了1,4-双（羟甲基）DeWar苯，并测定了其芳构化速率：在2,5-和2,6-位置上同时进行二氯取代，显著减缓了异构化过程。

  DOI：

  10.1246/cl.1990.1193

文献信息

• Syntheses of Acetylenic Oligophenylene Macrocycles Based on a Novel Dewar Benzene Building Block Approach
  作者：Masakazu Ohkita、Kohta Ando、Takanori Suzuki、Takashi Tsuji

  DOI：10.1021/jo0002590

  日期：2000.7.1

  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.