(Z)-1-acetyl-3-(5-chloro-2-hydroxy-4-methoxy)benzylidene-2,5-piperazinedione | 194488-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-1-acetyl-3-(5-chloro-2-hydroxy-4-methoxy)benzylidene-2,5-piperazinedione
• CAS: 194488-05-6
• 化学式: C₁₄H₁₃ClN₂O₅
• 分子量: 324.721
• InChiKey: BOVIFOUEPOICHW-WMZJFQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.94
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-acetyl-3-(5-chloro-2-hydroxy-4-methoxy)benzylidene-2,5-piperazinedione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到spiro[3H-5-chloro-3-hydroxy-6-methoxybenzofuran-2,3'-(1'-acetyl-2',5'-piperazinedione)]
  参考文献：
  名称：

  Synthesis of Aspirochlorine Precursors

  摘要：

  Synthesis of key precursors of aspirochlorine (1) and related compounds has been achieved in 5 steps from 1,4-diacetyl-2,5-piperazinedione (2), MCPBA mediated oxidative cyclization of 2-acetyl-3-salicylidene-2,5-piperazinedione (4) yielded a spiro 3 H-benzofuranol derivative (6) stereoselectively. Bromination of 6 by a 2-fluoropyridinium salt and sodium bromide, followed by NBS treatment yielded dibromide mixtures (8). Conversion of produced dibromides (8) to dithioacetates (9) by potassium thioacetate afforded all of four possible diastereomers. The ratio of the diastereomers was found to be solvent dependent.

  DOI：

  10.3987/com-97-7819
• 作为产物：
  描述：

  5-氯-2,4-二羟基苯甲醛 在 potassium tert-butylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (Z)-1-acetyl-3-(5-chloro-2-hydroxy-4-methoxy)benzylidene-2,5-piperazinedione
  参考文献：
  名称：

  Synthesis of Aspirochlorine Precursors

  摘要：

  Synthesis of key precursors of aspirochlorine (1) and related compounds has been achieved in 5 steps from 1,4-diacetyl-2,5-piperazinedione (2), MCPBA mediated oxidative cyclization of 2-acetyl-3-salicylidene-2,5-piperazinedione (4) yielded a spiro 3 H-benzofuranol derivative (6) stereoselectively. Bromination of 6 by a 2-fluoropyridinium salt and sodium bromide, followed by NBS treatment yielded dibromide mixtures (8). Conversion of produced dibromides (8) to dithioacetates (9) by potassium thioacetate afforded all of four possible diastereomers. The ratio of the diastereomers was found to be solvent dependent.

  DOI：

  10.3987/com-97-7819