spiro | 144018-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro
• 英文别名: Spiro[cyclopentene-3,9'-fluorene]
• CAS: 144018-46-2
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: JKNPYNKDZKJGDW-UHFFFAOYSA-N

物化性质

• 沸点：
  360.8±22.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  spiro 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以92%的产率得到
  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
• 作为产物：
  描述：

  9-芴甲酸 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 硫酸 、 potassium tert-butylate 、 sodium ethanolate 、 sodium hydride 作用下， 以 四氢呋喃 、 溶剂黄146 、 二甲基亚砜 、 甲苯 为溶剂， 反应 21.17h， 生成 spiro
  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

• Palladium-catalyzed coupling of 2,2t dihalobiaryls with metallated cyclopentenes. An easy synthesis for spiro[cyclopentene-1,9−[9H]fluorene]s
  作者：Thomas J. Katz、Adam M. Gilbert、Monika E. Huttenloch、Gu Min-Min、Hans H. Brintzinger

  DOI：10.1016/s0040-4039(00)73633-1

  日期：1993.5

  In the presence of palladium catalysts, one of the two carbons attached to halogen in 2,2'-diiodobiphenyl couples with unsaturated organometallics, after which the other adds to the newly incorporated double bond. Spiro[cyclopentene-1,9'-[9H]fluorene]s can be synthesized in this way.
• Orbital distortion arising from remote substituents. Nitration, reduction, and epoxidation of fluorenes bearing a carbonyl or an olefin group in spiro geometry
  作者：Tomohiko Ohwada

  DOI：10.1021/ja00049a012

  日期：1992.11

  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.