2,3-Bis(4-methylphenoxy)naphthalene-1,4-dione | 118210-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-Bis(4-methylphenoxy)naphthalene-1,4-dione
• CAS: 118210-23-4
• 化学式: C₂₄H₁₈O₄
• 分子量: 370.405
• InChiKey: GMBCRPNXHZPIJM-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C
• 沸点：
  489.6±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 对甲酚 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以82%的产率得到2,3-Bis(4-methylphenoxy)naphthalene-1,4-dione
  参考文献：
  名称：

  Substitution of a Haloquinone by Phenols under Pyridine-Free Conditions: Synthetic, Mechanistic, and Solid-State Considerations Involving 2,3-Dichloro-1,4-naphthoquinone

  摘要：

  Benzoquinones fused to heterocycles, like most benzoquinones, have the potential for a wide-array of applications but their inherent reactivity can present a synthetic dilemma. The issue is that a synthesis may target one desired outcome, yet yield a range of side products. In efforts to understand the reaction pathways of haloquinone substitution, while minimizing undesired product formation, four examples of reactions between 2,3-dichloro-1,4-naphthoquinone and phenolic nucleophiles are presented. Two of the products were confirmed and analyzed by X-ray crystallography. The reaction with orcinol was optimized for yield and investigation of this mechanism indicates a novel pathway under pyridine-free conditions.

  DOI：

  10.3987/com-19-14035

文献信息

• Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2010.05.071

  日期：2010.7

  Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles ‘on water’ is not facile. An unprecedented economical, green methodology approach

  最近我们已经证明了氮和硫亲核体与1，4-醌在胺和硫醇的水悬浮液中的独特亲核取代和加成反应。2然而，与“在水上”的氮和硫亲核试剂相比，氧亲核试剂对亲核取代的反应性并不容易。已经证明了一种空前的经济，绿色方法学方法，该方法使用普通洗衣粉（LD；洗衣粉，0.5 mol％，可重复使用）/ SDS作为表面活性剂“在水中”，以优异的产率被1,4-醌中的氧亲核试剂亲核取代。
• ISHIKAWA, SEIICHI;HINOSHITA, HIROTAKA;TAKAGI, MAKOTO;UENO, KEIHEI, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1988) N 5, 743-751
  作者：ISHIKAWA, SEIICHI、HINOSHITA, HIROTAKA、TAKAGI, MAKOTO、UENO, KEIHEI

  DOI：——

  日期：——