6-(1-propenyl)-2,3-dichlorophenol | 377741-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(1-propenyl)-2,3-dichlorophenol
• 英文别名: 2,3-Dichloro-6-prop-1-enylphenol；2,3-dichloro-6-prop-1-enylphenol
• CAS: 377741-28-1
• 化学式: C₉H₈Cl₂O
• 分子量: 203.068
• InChiKey: UERCOOUJBZYWMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(1-propenyl)-2,3-dichlorophenol 在 对甲苯磺酸 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 、 苯 为溶剂， 反应 24.5h， 生成 2,3-dichloro-6-[1,3]dioxolan-2-ylphenol
  参考文献：
  名称：

  Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands

  摘要：

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).

  DOI：

  10.1021/jm010948j
• 作为产物：
  描述：

  2,3-dichloro-6-propenylphenol 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以84%的产率得到6-(1-propenyl)-2,3-dichlorophenol
  参考文献：
  名称：

  Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands

  摘要：

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).

  DOI：

  10.1021/jm010948j

文献信息

• Salicylaldoxime Moiety as a Phenolic “A-Ring” Substitute in Estrogen Receptor Ligands
  作者：Filippo Minutolo、Simone Bertini、Chiara Papi、Kathryn E. Carlson、John A. Katzenellenbogen、Marco Macchia

  DOI：10.1021/jm010948j

  日期：2001.11.1

  The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).