2,10-diacetyl-3-hydroxyphenothiazine | 1344686-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,10-diacetyl-3-hydroxyphenothiazine
• CAS: 1344686-53-8
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: PDASIEQUIQPDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,10-diacetyl-3-hydroxyphenothiazine 在 吡啶 、 potassium hydroxide 、 三氯氧磷 作用下， 反应 1.0h， 生成 1-(10-acetyl-10H-3-hydroxyphenothiazin-2-yl)-3-(4-chlorophenyl)propane-1,3-dione
  参考文献：
  名称：

  Synthesis of New 2-Phenylpyrano[3,2-b]phenothiazin-4(6H)-one Derivatives

  摘要：

  AbstractA new synthesis of 2‐phenylpyrano[3,2‐b]phenothiazin‐4(6H)‐one derivatives was reported. First 2,10‐diacetyl‐3‐hydroxyphenothiazine (2) was converted into their benzoyloxy esters (3a–3j) using different aromatic carboxylic acids in the presence of phosphorous oxychloride in pyridine. Benzoyloxy esters were converted into their 1,3‐diones (4a–4j) by using dry KOH in pyridine via Baker‐Venkataraman transformation reaction. The 1,3‐diones thus obtained were cyclised to pyranophenothiazines (5a–5j) by refluxing in an acetic acid/HCl mixture.

  DOI：

  10.1002/cjoc.201100033
• 作为产物：
  描述：

  1-(3-methoxy-10H-phenothiazin-10-yl)ethan-1-one 、 乙酰氯 在 aluminum (III) chloride 作用下， 以 二硫化碳 为溶剂， 反应 5.0h， 以80%的产率得到2,10-diacetyl-3-hydroxyphenothiazine
  参考文献：
  名称：

  Synthesis of New 2-Phenylpyrano[3,2-b]phenothiazin-4(6H)-one Derivatives

  摘要：

  AbstractA new synthesis of 2‐phenylpyrano[3,2‐b]phenothiazin‐4(6H)‐one derivatives was reported. First 2,10‐diacetyl‐3‐hydroxyphenothiazine (2) was converted into their benzoyloxy esters (3a–3j) using different aromatic carboxylic acids in the presence of phosphorous oxychloride in pyridine. Benzoyloxy esters were converted into their 1,3‐diones (4a–4j) by using dry KOH in pyridine via Baker‐Venkataraman transformation reaction. The 1,3‐diones thus obtained were cyclised to pyranophenothiazines (5a–5j) by refluxing in an acetic acid/HCl mixture.

  DOI：

  10.1002/cjoc.201100033