6-(2-phenylethenyl)fulvene | 32174-25-7

• 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: 6-(2-phenylethenyl)fulvene
• 英文别名: [(1E)-3-cyclopenta-2,4-dien-1-ylideneprop-1-en-1-yl]benzene；[(E)-3-cyclopenta-2,4-dien-1-ylideneprop-1-enyl]benzene
• CAS: 32174-25-7
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: XYJUKARVJMWHBT-IZZDOVSWSA-N

物化性质

• 沸点：
  329.4±9.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6-(2-phenylethenyl)fulvene 以 环己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 6-tert-butyl-1-(3-phenyl-allylidene)-1H-indene
  参考文献：
  名称：

  6芳基烯基富烯与二烯和亲二烯体的Diels-Alder反应及相关化学

  摘要：

  已经表明6-（2-苯基乙烯基）富烯烯以二烯和亲二烯体的形式参与Diels-Alder反应，并且已经完成了导致广泛共轭的苯并富烯酮的双环[2.2.2]-辛二酮的光化学转化。

  DOI：

  10.1016/s0040-4020(97)10160-0
• 作为产物：
  描述：

  反式肉桂醛 、 环戊二烯 在 四氢吡咯 作用下， 以62%的产率得到6-(2-phenylethenyl)fulvene
  参考文献：
  名称：

  Scope and Limitations of Fulvene Syntheses. Preparation of 6-Vinyl-Substituted and -Functionalized Fulvenes. First Examples of Nucleophilic Substitution on a 6-(Chloromethyl)fulvene

  摘要：

  Very few 6-vinylfulvenes have previously been reported in the Literature. In a few cases where Little's procedure (using pyrrolidine as base) has been employed, most enones undergo conjugate attack by the cyclopentadienyl anion followed by either a retroaldol reaction or dihydropentalene formation. In several cases, Diels-Alder reaction of the enone with cyclopentadiene occurs rather than condensation. We have found that in cases where the Little procedure fails to give the desired 6-vinylfulvenes, the Thiele method using NaOH (or NaOMe in some cases) as base gives satisfactory results. In the latter instances, Michael attack is completely suppressed in all but one example. By appropriate choice of base, a variety of fulvenes carrying functional groups on the 6-alkyl position can be prepared. Some of these fulvenes have been shown to undergo further functional group transformations (e.g., nucleophilic substitutions); giving rise to derivatives bearing SR, S(O)R, N-3 or SCN groups.

  DOI：

  10.1021/jo00109a010

文献信息

• Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans
  作者：Haifeng Zheng、Chaoran Xu、Yan Wang、Tengfei Kang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/c7cc03211k

  日期：——

  The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(II) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal

  通过使用手性铜（II）络合物催化剂，首次实现了醌与富烯之间的催化对映选择性[2 + 2]环加成反应。该转化以良好的产率提供了一系列对映异构体富集的[6,4,5]-三环环丁烷衍生物，具有优异的区域选择性和立体选择性。此外，[2 + 2]加合物可以轻松有效地和立体选择性地转化为正式的[3 + 2]加合物。
• 1,3-Dipolar Cycloaddition Reaction of Nitrile N-Oxides to 6-(2-Phenylethenyl)fulvene
  作者：Vijay Nair、M.V Nandakumar、Davis Maliakal、Joseph Swaroop Mathen、Nigam P Rath

  DOI：10.1016/s0040-4020(00)00718-3

  日期：2000.9

  Dipolar cycloaddition reactions of aryl nitrile oxides to 6-(2-phenylethenyl)fulvene leading to isoxazolines are described.

  描述了芳基腈氧化物与6-（2-苯基乙烯基）富烯的偶极环加成反应，导致异恶唑啉。
• Hetero-Diels-Alder Reaction of 3-Bromo-7-(bromomethyl)tetracyclo[5.3.1.0^2,6.0^4,8]undec-10(12)-ene-9,11-dione with Pentafulvenes: Facile Synthesis of Novel Polycyclic Cage Compounds Having a Pyran Ring
  作者：Mangalam Nair、Beena James、E. Suresh

  DOI：10.1055/s-2006-956481

  日期：2006.12

  The enone moiety of 3-bromo-7-(bromomethyl)tetracyclo[5.3.1.02,6.04,8]undec-10(12)-ene-9,11-dione undergoes facile hetero-Diels-Alder reaction with pentafulvenes leading to novel cage systems with pyran moiety

  3-溴-7-(溴甲基)四环[5.3.1.02,6.04,8]十一碳-10(12)-烯-9,11-二酮的烯酮部分与五氟乙烯发生易异构化的Diels-Alder反应，形成具有吡喃部分的全新笼状系统。
• Diels-Alder Reactions of a 6-Arenyl Fulvene Participating both as Diene and Dienophile
  作者：Vijay Nair、Anilkumar Nair、K. Radhakrishnan、M. Nandakumar、Nigam Rath

  DOI：10.1055/s-1997-5763

  日期：1997.7

  Diels-Alder reactions of 6-(2-phenylethenyl)fulvene with electron deficient dienophiles and dienes are described. The participation of the fulvene both as 4π and 2π addend is rationalised using MNDO and AM1 calculations.

  描述了 6-(2-苯基乙烯基) 富烯与缺电子亲二烯体和二烯的 Diels-Alder 反应。富烯作为 4π 和 2π 加数的参与使用 MNDO 和 AM1 计算进行了合理化。
• [4+2] Cycloaddition reactions of o-thioquinones with pentafulvenes: efficient synthesis of benzoxathiins
  作者：Vijay Nair、Bini Mathew、Rajeev S Menon、Saumini Mathew、M Vairamani、S Prabhakar

  DOI：10.1016/s0040-4020(02)00263-6

  日期：2002.4

  o-Thioquinones undergo [4+2] cycloaddition reactions with pentafulvenes leading to 1,4-benzoxathiins. Reactions of 6-styrenylfulvene with o-thioquinones also afforded similar products. (C) 2002 Published by Elsevier Science Ltd.

表征谱图