ethyl 2-cyano(3-hydroxy-4-oxonaphthalen-1-ylidene)acetate | 1253123-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-cyano(3-hydroxy-4-oxonaphthalen-1-ylidene)acetate
• 英文别名: cyano-(3-hydroxy-4-oxo-4H-naphthalen-1-ylidene)acetic acid ethyl ester；ethyl 2-cyano-2-(3-hydroxy-4-oxonaphthalen-1-ylidene)acetate
• CAS: 1253123-87-3
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: PUACVSRCISFFSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.39
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  sodium 1,2-naphthoquinone-4-sulfonate 、 氰乙酸乙酯 在 potassium tert-butylate 作用下， 以 PEG 300 为溶剂， 以54%的产率得到ethyl 2-cyano(3-hydroxy-4-oxonaphthalen-1-ylidene)acetate
  参考文献：
  名称：

  Polyethylene Glycol (PEG 300) and Water–Ethanol as Benign Solvent Systems for the Synthesis of a Novel Series of 2-Hydroxynaphthalen-1(4H)-Ones

  摘要：

  An improved, clean, simple, and efficient method for the synthesis of new series of 2-hydroxy-4-methylenenaphthalen-1(4H)-one is described. This new process involves a domino Michael addition of various methylene acid compounds with the sodium salt of 1,2-naphthoquinone-4-sulfonate either in basic (tBuOK) polyethylene glycol (PEG300) at room temperature or in a basic (NaOH) water-ethanol medium at 40 degrees C by a crushing in a mortar or a traditional heating.

  DOI：

  10.1080/00397911003797916

文献信息

• A Green Route for Synthesis of New 1,2-Naphthoquinomethane Acetonitriles in Water
  作者：Didier Villemin、Mohammed Benabdallah、Nadjib Rahmoun、Cyril Jouannic、Noureddine Choukchou-Braham、Bachir Mostefa-Kara

  DOI：10.1080/00397910903457340

  日期：2010.11.3

  A series of new 2-(3-hydroxy-4-oxo-4H-naphthalen-1-ylidene) acetonitriles was prepared by the cascade Michael addition-elimination reaction of sodium 1,2-naphthoquinone-4-sulfonate with various substituted acetonitriles compounds in ethanol-water in presence of basic catalyst.