3-hydroxyacetophenone | 1644568-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxyacetophenone
• CAS: 1644568-79-5
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: ZKDIGGGRKDDFMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-hydroxyacetophenone 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 1,2-二溴乙烷 为溶剂， 反应 4.0h， 生成 (E)-1-(benzo[d][1,3]oxathiol-6-yl)-3-(3-fluoro-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives

  摘要：

  Derivatives of (E)‐1‐(5‐alkoxybenzo[d][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.

  DOI：

  10.1111/cbdd.12296
• 作为产物：
  描述：

  香草乙酮 在 二甲基硫 、 三氟化硼 作用下， 以 四氢呋喃 、 二苯醚 、 二氯甲烷 、 水 为溶剂， 生成 3-hydroxyacetophenone
  参考文献：
  名称：

  Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives

  摘要：

  Derivatives of (E)‐1‐(5‐alkoxybenzo[d][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.

  DOI：

  10.1111/cbdd.12296