(Z)-1-acetyl-3-(naphthalene-1-yl-methylene)-piperazine-2,5-dione | 1393792-54-5

• 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-1-yl-methylene)-piperazine-2,5-dione
• 英文别名: (Z)-1-acetyl-3-(naphthalene-1-ylmethylene)piperazine-2,5-dione
• CAS: 1393792-54-5
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: VWZCMCNTRAMMOF-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-1-yl-methylene)-piperazine-2,5-dione 在 盐酸 、 水 作用下， 反应 4.0h， 以95%的产率得到(Z)-2-hydroxy-3-(naphthalen-1-yl)-acrylic acid
  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
• 作为产物：
  描述：

  1,4-二乙酰基哌嗪-2,5-二酮 、 1-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79%的产率得到(Z)-1-acetyl-3-(naphthalene-1-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

文献信息

• Enantiomerically Pure 3-Aryl- and 3-Hetaryl-2-hydroxypropanoic Acids by Chemoenzymatic Reduction of 2-Oxo Acids
  作者：Sivatharushan Sivanathan、Florian Körber、Jannis Aron Tent、Svenja Werner、Jürgen Scherkenbeck

  DOI：10.1021/jo502529g

  日期：2015.3.6

  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.