5,5-Dimethyl-1,4-diphenylcyclopenta-1,3-diene | 33930-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-Dimethyl-1,4-diphenylcyclopenta-1,3-diene
• 英文别名: 5,5-Dimethyl-1,4-diphenylcyclopentadien；1,4-Diphenyl-5,5-dimethylcyclopentadien；(5,5-Dimethyl-4-phenyl-1,3-cyclopentadien-1-yl)benzene；(5,5-dimethyl-4-phenylcyclopenta-1,3-dien-1-yl)benzene
• CAS: 33930-83-5
• 化学式: C₁₉H₁₈
• 分子量: 246.352
• InChiKey: CARFRWAWKOJPBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,2-二甲基环戊烷-1,3-二酮 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 双(三甲基硅烷基)氨基钾 、 三环己基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 生成 5,5-Dimethyl-1,4-diphenylcyclopenta-1,3-diene
  参考文献：
  名称：

  降低π共轭材料的芳香性：含环戊二烯的系统的高效合成和电子结构鉴定

  摘要：

  报道了一种制备含环戊二烯的π-共轭分子的有效途径。芳基/二烯杂化物和它们的芳族同类物之间的比较分析表明，二烯部分倾向于在不损害平面结构拓扑的情况下减小π-共轭体系的光学带隙。此外，合成了带有交替的环戊二烯重复单元的新型聚芴衍生物，以证明该方法在聚合物合成中的适用性。

  DOI：

  10.1021/ol402824m

文献信息

• Photosensitized electron transfer from azoalkanes: generation, fragmentation, and rearrangement of radical cations structurally related to dicyclopentadiene
  作者：Waldemar Adam、Juergen Sendelbach

  DOI：10.1021/jo00072a008

  日期：1993.9

  The azoalkanes 1a-c extrude nitrogen upon photosensitized electron transfer (PET) to yield 1,3-radical cation intermediates 2.+, which undergo interesting transformations. Electron back transfer (BET) affords the unrearranged housanes 2, but significant rearrangement to dicyclopentadiene derivatives 3 occurs prior to BET. In some cases, fragmentation to cyclopentadienes 4 is observed, a cycloreversion that occurs at the 1,3-radial cation stage rather than through the corresponding 1,3-biradical intermediates. The diphenyl-substituted azoalkane la affords high yields of the symmetric cyclopentadiene 4a, while the alkyl-substituted lb produces only small amounts of a rearranged cyclopentadiene 4'b. The housanes 2a,b are also oxidized by PET, but are more reluctant to rearrange. Strong electron acceptors such as triphenylpyrylium tetrafluoroborate (TPT) or cosensitization with biphenyl (Ph2) must be utilized to induce rearrangement to 3a,b and fragmentation to 4 and 4'.
• Thermally promoted cleavage reactions of anti-tricyclo[3.2.0.02,4] heptanes. Influence of 2,4 substitution on competitive bond scission processes
  作者：Leo A. Paquette、Louis M. Leichter

  DOI：10.1021/jo00918a009

  日期：1974.2
• Decreasing Aromaticity in π-Conjugated Materials: Efficient Synthesis and Electronic Structure Identification of Cyclopentadiene-Containing Systems
  作者：Lei Chen、Sufian M. Mahmoud、Xiaodong Yin、Roger A. Lalancette、Agostino Pietrangelo

  DOI：10.1021/ol402824m

  日期：2013.12.6

  An efficient route to cyclopentadiene-containing π-conjugated molecules is reported. A comparative analysis between the aryl/dienyl hybrids and their aromatic congeners shows a propensity of the diene moiety to reduce the optical band gap of a π-conjugated system without compromising a planar structural topology. Moreover, a novel poly(fluorene) derivative bearing alternating cyclopentadiene repeat

  报道了一种制备含环戊二烯的π-共轭分子的有效途径。芳基/二烯杂化物和它们的芳族同类物之间的比较分析表明，二烯部分倾向于在不损害平面结构拓扑的情况下减小π-共轭体系的光学带隙。此外，合成了带有交替的环戊二烯重复单元的新型聚芴衍生物，以证明该方法在聚合物合成中的适用性。