9-<2'-(ethoxycarbonyl)vinyl>-10-methylanthracene | 916665-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-<2'-(ethoxycarbonyl)vinyl>-10-methylanthracene
• 英文别名: 9-[2'-(ethoxycarbonyl)vinyl]-10-methylanthracene
• CAS: 916665-93-5
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: NWRCAKIPRDMTBP-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-<2'-(ethoxycarbonyl)vinyl>-10-methylanthracene 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到9-[2'-(ethoxycarbonyl)ethyl]-10-methylanthracene
  参考文献：
  名称：

  A Nitroxyl Synthase Catalytic Antibody

  摘要：

  An antibody raised against acridinium hapten 1 is shown to catalyze the retro Diels-Alder reaction of the anthracene-HNO cycloadduct 2 to release anthracene 4 and nitroxyl (HNO). Nitroxyl is oxidized to nitric oxide (NO) in the presence of superoxide dismutase. Since the enzyme superoxide dismutase is ubiquitous in vivo, this catalytic antibody system may be equivalent to NO-synthase. Antibody catalysis is triggered by recognition of the phenyl rings in hapten 1 at an angle near that of the transition state of the retro Diels-Alder reaction of 2. Acridinium hapten 1 is in chemical equilibrium with its conjugate Lewis base 9-hydroxyacridane 1-OH (pK similar to 8.2). Catalytic antibody 9D9 (K-M(2) = 100 mu M, k(cat) = 0.07 min(-1), k(uncat) = 3 x 10(-4) min(-1)) is the result of an heterologous immunization and binds both 1 (K-i = 16.6 mu M at pH 6.1) and 1-OH (K-i = 0.9 mu M at pH 9.0). The more tightly bound neutral conjugate base 1-OH probably represents a more accurate mimic of the transition state of the retro Diels-Alder process.

  DOI：

  10.1021/ja9538694
• 作为产物：
  描述：

  10-甲基蒽-9-甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 反应 36.0h， 以93%的产率得到9-<2'-(ethoxycarbonyl)vinyl>-10-methylanthracene
  参考文献：
  名称：

  A Nitroxyl Synthase Catalytic Antibody

  摘要：

  An antibody raised against acridinium hapten 1 is shown to catalyze the retro Diels-Alder reaction of the anthracene-HNO cycloadduct 2 to release anthracene 4 and nitroxyl (HNO). Nitroxyl is oxidized to nitric oxide (NO) in the presence of superoxide dismutase. Since the enzyme superoxide dismutase is ubiquitous in vivo, this catalytic antibody system may be equivalent to NO-synthase. Antibody catalysis is triggered by recognition of the phenyl rings in hapten 1 at an angle near that of the transition state of the retro Diels-Alder reaction of 2. Acridinium hapten 1 is in chemical equilibrium with its conjugate Lewis base 9-hydroxyacridane 1-OH (pK similar to 8.2). Catalytic antibody 9D9 (K-M(2) = 100 mu M, k(cat) = 0.07 min(-1), k(uncat) = 3 x 10(-4) min(-1)) is the result of an heterologous immunization and binds both 1 (K-i = 16.6 mu M at pH 6.1) and 1-OH (K-i = 0.9 mu M at pH 9.0). The more tightly bound neutral conjugate base 1-OH probably represents a more accurate mimic of the transition state of the retro Diels-Alder process.

  DOI：

  10.1021/ja9538694

文献信息

• Grignard Reagent-Mediated Conversion of an Acyl Nitroso-anthracene Cycloadduct to a Nitrone
  作者：Weibin Chen、Cynthia S. Day、S. Bruce King

  DOI：10.1021/jo0615192

  日期：2006.11.1

  An intramolecular hetero-Diels−Alder cycloadduct of an acyl nitroso compound and a 9,10-dimethyl anthracene derivative was prepared as a potential nitroxyl (HNO) donor. This compound did not release HNO under any of the conditions tested. Treatment of this cycloadduct with excess MeMgCl resulted in the formation of a nitrone, whose structure was confirmed by X-ray crystallography. A mechanism where

  酰基亚硝基化合物和9,10-二甲基蒽衍生物的分子内杂Diels-Alder环加合物被制备为潜在的硝酰基（HNO）供体。该化合物在任何测试条件下均不释放HNO。用过量的MeMgCl处理该环加合物导致形成硝酮，其结构通过X射线晶体学证实。MeMgCl充当亲核试剂，强碱和路易斯酸的机理可能解释了该产物的形成。