2-nitro-9-(ethoxycarbonyl)fluorene | 138112-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-nitro-9-(ethoxycarbonyl)fluorene
• 英文别名: ethyl 2-nitro-9H-fluorene-9-carboxylate
• CAS: 138112-64-8
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: DCWRRPWZZCBJAX-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  9-芴甲酸 在 硫酸 、 硝酸 、 乙酸酐 作用下， 反应 11.5h， 生成 2-nitro-9-(ethoxycarbonyl)fluorene
  参考文献：
  名称：

  Orbital distortion arising from remote substituents. Nitration, reduction, and epoxidation of fluorenes bearing a carbonyl or an olefin group in spiro geometry

  摘要：

  Nitration of spiro[cyclopentane-1,9'-fluoren]-2-one with acetyl nitrate predominantly gave the 4-nitro derivative. In the reduction of substituted spiro[cyclopentane-1,9-fluoren]-2-ones, the anti alcohols were favored in all cases. In the epoxidation of substituted spiro[cyclopent-2-ene-1,9'-fluorenes], the syn epoxides were favored. These distributions of the products can be interpreted in terms of orbital perturbations arising from interactions of the pi orbitals of the aromatic and the carbonyl moieties or of the pi orbitals of the aromatic and the olefin moieties, i.e., orbital mixing perturbation of the aromatic pi orbitals through the pi orbital of the bisected carbonyl (or olefin) group and the reciprocal perturbation of the pi orbital of the carbonyl (or olefin) group arising from the orthogonal pi aromatic orbitals.

  DOI：

  10.1021/ja00049a012

文献信息

• Orbital distortion arising from remote substituents nitration and reduction of spiro(cyclopenta-1,9'-fluorene)-2-ones.
  作者：Tomohiko OHWADA、Koichi SHUDO

  DOI：10.1248/cpb.39.2176

  日期：——

  Nitration of spiro[cyclopenta-1, 9'-fluorene]-2-one with acetyl nitrate predominantly gave the 4-nitro derivative. In the reduction of substituted spiro[cyclopenta-1, 9'-fluorene]-2-ones, the anti-alcohols were favored in all cases. Both anomalous distributions of the products can be interpreted in terms of interactions of the π orbitals of the aromatic and the carbonyl moieties. This example of stereoelectronic effects demonstrates intrinsic reciprocal distortion between sterically unbiased π frameworks of the molecule.

  螺[环戊-1, 9'-芴]-2-酮与乙酰基硝酸盐的硝化主要产生4-硝基衍生物。在取代螺[环戊-1, 9'-芴]-2-酮的还原中，在所有情况下，抗醇剂都受到青睐。产物的两种反常分布都可以用芳香族和羰基部分的π轨道的相互作用来解释。这个立体电子效应的例子证明了分子空间无偏 π 框架之间固有的相互畸变。