spiro[cyclohexane-1,9’-fluoren]-4-one | 98656-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro[cyclohexane-1,9’-fluoren]-4-one
• 英文别名: 4H-Spiro[cyclohexane-1,9'-fluoren]-4-one；spiro[cyclohexane-4,9'-fluorene]-1-one
• CAS: 98656-46-3
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: FSRGUIQAZVVJKN-UHFFFAOYSA-N

物化性质

• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  spiro[cyclohexane-1,9’-fluoren]-4-one 在 氢氧化钾 、 一水合肼 作用下， 生成 螺[环己烷-1,9'-芴]
  参考文献：
  名称：

  The Synthesis of Spiro[cyclohexane-1,9'-fluorene] and Related Compounds¹

  摘要：

  DOI：

  10.1021/jo01067a060
• 作为产物：
  描述：

  9,9-二(2-氰基乙基)芴 在 磷酸 、 叔丁醇 作用下， 以 溶剂黄146 为溶剂， 生成 spiro[cyclohexane-1,9’-fluoren]-4-one
  参考文献：
  名称：

  The Synthesis of Spiro[cyclohexane-1,9'-fluorene] and Related Compounds¹

  摘要：

  DOI：

  10.1021/jo01067a060

文献信息

• From Wires to Cables: Attempted Synthesis of 1,3,5-Trifluorenylcyclohexane as a Platform for Molecular Cables
  作者：Marat R. Talipov、Sameh H. Abdelwahed、Khushabu Thakur、Scott A. Reid、Rajendra Rathore

  DOI：10.1021/acs.joc.5b02792

  日期：2016.2.19

  analogues (DFCs) were systematically investigated both experimentally (X-ray crystallography) and theoretically (DFT calculations). Although the syntheses of DFCs were successfully achieved, the synthesis of TFC, which involved a similar intramolecular Friedel–Crafts cyclization as the last step, was unsuccessful. An exhaustive study of the conformational landscape of cyclohexane ring of TFC and DFCs

  在单个组件中编织在一起的多条分子线，称为分子电缆，是有效进行长距离电荷传输的有前途的下一代材料。作为构建分子电缆平台的一个例子，对1,3,5-三芴基环己烷（TFC）及其二芴基类似物（DFC s）进行了系统的实验研究（X射线晶体学）和理论上的研究（DFT计算）。尽管成功地完成了DFC的合成，但最后一步涉及分子内Friedel-Crafts分子内类似的环化的TFC合成仍未成功。对TFC和DFC的环己烷环构象进行详尽的研究。s揭示TFC是一个中等应变的分子（〜17 kcal / mol），并且对反应曲线的计算研究表明，这种处于过渡态的空间应变是导致异常高（约5年）反应的一半。生活。TFC的成功合成将需要在多个步骤中引入空间菌株，目前正在探索这种替代策略。
• Novel arylamine compound and organic electroluminescence device
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：US20020137969A1

  公开（公告）日：2002-09-26

  A novel arylamine compound represented by the following general formula (1): 1 wherein R 1 and R 2 each independently represent an alkyl group, an alkoxyl group, an aryl group, an arylalkyl group or an aryloxyl group, Ar 1 to Ar 4 each independently represent an aryl group or a heterocyclic group, with provisos that at least two of Ar 1 to Ar 4 each represent m-biphenyl group or a biphenyl group substituted with aryl groups and the others of Ar 1 to Ar 4 each represent biphenyl group and that, when the biphenyl group substituted with aryl groups is a biphenyl group substituted with two aryl groups, the others of Ar 1 to Ar 4 each represent an aryl group; and an organic electroluminescence device comprising a layer of organic compounds which comprises the novel arylamine compound. The organic electroluminescence device has a high luminance, excellent heat resistance and a long life and emits light; at a high efficiency. The novel arylamine compound provides the advantageous properties to the organic electroluminescence device.

  一种新的芳胺化合物，其通式如下（1）： 其中R1和R2分别独立表示烷基、烷氧基、芳基、芳基烷基或芳氧基，Ar1至Ar4分别独立表示芳基或杂环基，但至少两个Ar1至Ar4中的每一个表示m-联苯基或被芳基取代的联苯基，其余的Ar1至Ar4中的每一个表示联苯基；以及包括该新的芳胺化合物的有机电致发光器件。该有机电致发光器件具有高亮度、优异的耐热性和长寿命，并以高效率发光。该新的芳胺化合物为有机电致发光器件提供了有利的性能。
• 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。
• NOVEL ARYLAMINE COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：EP1219590A1

  公开（公告）日：2002-07-03

  A novel arylamine compound represented by the following general formula (1): wherein R1 and R2 each independently represent an alkyl group, an alkoxyl group, an aryl group, an arylalkyl group or an aryloxyl group, Ar1 to Ar4 each independently represent an aryl group or a heterocyclic group, with provisos that at least two of Ar1 to Ar4 each represent m-biphenyl group or a biphenyl group substituted with aryl groups and the others of Ar1 to Ar4 each represent biphenyl group and that, when the biphenyl group substituted with aryl groups is a biphenyl group substituted with two aryl groups, the others of Ar1 to Ar4 each represent an aryl group; and an organic electroluminescence device comprising a layer of organic compounds which comprises the novel arylamine compound. The organic electroluminescence device has a high luminance, excellent heat resistance and a long life and emits light at a high efficiency. The novel arylamine compound provides the advantageous properties to the organic electroluminescence device.

  由以下通式(1)代表的新型芳胺化合物： 其中 R1 和 R2 各自独立地代表烷基、烷氧基、芳基、芳烷基或芳基环氧基，Ar1 至 Ar4 各自独立地代表芳基或杂环基、但前提是 Ar1 至 Ar4 中至少有两个各自代表间联苯基团或被芳基取代的联苯基团，Ar1 至 Ar4 中的其它两个各自代表联苯基团，当被芳基取代的联苯基团是被两个芳基取代的联苯基团时，Ar1 至 Ar4 中的其它两个各自代表芳基；以及一种有机电致发光器件，该器件包括一层有机化合物，其中包含该新型芳基胺化合物。该有机电致发光器件具有高亮度、优异的耐热性和较长的使用寿命，并能高效发光。新型芳胺化合物为有机电致发光器件提供了有利的特性。
• Free energy and structure dependence of intramolecular triplet energy transfer in organic model compounds
  作者：Michael E. Sigman、Gerhard L. Closs

  DOI：10.1021/j100166a022

  日期：1991.6

  A series of compounds, each containing a triplet energy donor and an acceptor separated by a rigid spacer, has been designed and synthesized. The 1,4-cyclohexanediyl moiety is employed as the spacer for the series. The rates of intramolecular triplet energy transfer (TT) have been measured for the series. The rate of TT shows an inverted parabolic, i.e., Marcus, dependence on the thermodynamic driving force for a selected subset of the compounds wherein the donor is maintained constant throughout and the acceptors are "rigid", having no low-frequency internal degrees of freedom. The internal low-frequency torsional mode of a biphenylyl acceptor can be accounted for quite satisfactorily as an additional contribution to the solvent reorganization energy, lambda-s. The driving force dependence of the rate of TT is not modeled well by the conventional Marcus-Jortner equation for weakly coupled nonadiabatic electron transfer. Generalization of the Marcus-Jortner equation to include coupling to a high-frequency harmonic mode which is both displaced and distorted along the reaction coordinate provides a somewhat better fit to the experimental data with fewer adjustable parameters.