(Z)-1-acetyl-3-(naphthalene-2-yl-methylene)-piperazine-2,5-dione | 1393792-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-acetyl-3-(naphthalene-2-yl-methylene)-piperazine-2,5-dione
• 英文别名: (Z)-1-acetyl-3-(naphthalene-2-ylmethylene)piperazine-2,5-dione
• CAS: 1393792-55-6
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: YVFAHODNBZKAIG-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  22.0
• 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：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-acetyl-3-(naphthalene-2-yl-methylene)-piperazine-2,5-dione 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2-氧代-3-(2-萘基)丙酸
  参考文献：
  名称：

  Enantiomerically Pure 3-Aryl- and 3-Hetaryl-2-hydroxypropanoic Acids by Chemoenzymatic Reduction of 2-Oxo Acids

  摘要：

  Phenyllactic acids are found in numerous natural products as well as in active substances used in medicine or plant protection. Enantiomerically pure phenyllactic acids are available by transition-metal-catalyzed hydrogenations or chemoenzymatic reductions of the corresponding 3-aryl-2-oxopropanoic acids. We show here that d-lactate dehydrogenase from Staphylococcus epidermidis reduces a broad spectrum of 2-oxo acids, which are difficult substrates for transition-metal-catalyzed reactions, with excellent enantioselectivities in a simple experimental setup.

  DOI：

  10.1021/jo502529g
• 作为产物：
  描述：

  1,4-二乙酰基哌嗪-2,5-二酮 、 2-萘甲醛 在 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 3.0h， 以73%的产率得到(Z)-1-acetyl-3-(naphthalene-2-yl-methylene)-piperazine-2,5-dione
  参考文献：
  名称：

  Novel approach to the synthesis of aliphatic and aromatic α-keto acids

  摘要：

  A new practical and efficient synthesis of alpha-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.078