6-phenyl-1,2-benzofulvene | 5394-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 6-phenyl-1,2-benzofulvene
• 英文别名: 1-(H)-Indene, 1-phenylmethylene-；1-benzylidene-1H-indene；1-benzylidene-indene；1-Benzyliden-inden；3-Benzalinden；1-benzylideneindene
• CAS: 5394-86-5
• 化学式: C₁₆H₁₂
• 分子量: 204.271
• InChiKey: SJWIOZSGMUJDFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  339.9±12.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• 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

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  6-phenyl-1,2-benzofulvene 、 苯基锂 在 乙醚 作用下， 生成 3-Benzhydryl-inden
  参考文献：
  名称：

  Ziegler; Schaefer, Justus Liebigs Annalen der Chemie, 1934, vol. 511, p. 101,107

  摘要：

  DOI：
• 作为产物：
  描述：

  Lithium; (1H-inden-1-yl)-phenyl-methanolate 在 碘甲烷 作用下， 以50%的产率得到6-phenyl-1,2-benzofulvene
  参考文献：
  名称：

  Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol

  摘要：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

  DOI：

  10.1021/jo00007a033

文献信息

• Addition and Cyclization Reactions in the Thermal Conversion of Hydrocarbons with an Enyne Structure, 5. High-Temperature Ring Closures of 1,3-Hexadien-5-ynes to Naphthalenes – Competing Reactions via Isoaromatics, Alkenylidene Carbenes, and Vinyl-type Radicals
  作者：Jörg Hofmann、Kathrin Schulz、Annett Altmann、Matthias Findeisen、Gerhard Zimmermann

  DOI：10.1002/jlac.199719971218

  日期：1997.12

  2-ethynylstyrenes 7a–c were subjected to high-temperature pyrolysis. The cycloisomerization products isolated suggest that these are formed by three competing processes: by (i) an electrocyclic or a molecule-induced, (ii) an alkenylidene carbene controlled, and (iii) a radical-controlled ring-closure process. To estimate the relative importance of these three reactions here mentioned, the substrates have

  对4-取代的1-苯基-1-丁烯-3-炔1a-c和2-乙炔基苯乙烯7a-c进行了高温热解。分离出的环异构化产物表明，它们是由三个竞争过程形成的：（i）电环或分子诱导的；（ii）链烯基卡宾控制的，和（iii）自由基控制的闭环过程。为了评估此处提到的这三个反应的相对重要性，分别在700和650°C的无氧氮气中和在甲苯中按比例取代的氮气中异构化了底物。这些异构化的相对贡献不仅取决于转化温度，而且还对在取代基- [R 1或7。
• The Missing C₁–C₅ Cycloaromatization Reaction: Triplet State Antiaromaticity Relief and Self-Terminating Photorelease of Formaldehyde for Synthesis of Fulvenes from Enynes
  作者：Rana K. Mohamed、Sayantan Mondal、Kjell Jorner、Thais Faria Delgado、Vladislav V. Lobodin、Henrik Ottosson、Igor V. Alabugin

  DOI：10.1021/jacs.5b07448

  日期：2015.12.16

  example of the four archetypical cycloaromatizations of enediynes and enynes was discovered by combining a twisted alkene excited state with a new self-terminating path for intramolecular conversion of diradicals into closed-shell products. Photoexcitation of aromatic enynes to a twisted alkene triplet state creates a unique stereoelectronic situation, which is facilitated by the relief of excited state

  通过将扭曲的烯烃激发态与用于双自由基分子内转化为闭壳产物的新自终止路径相结合，发现了烯二炔和烯炔的四种原型环芳构化的最后一个缺失的例子。芳香烯炔光激发到扭曲的烯烃三重态创造了一种独特的立体电子情况，这是由苯环的激发态反芳香性的释放所促进的。这使得通常不利的 5-endo-trig 环化成为可能，并将其与 5-exo-dig 闭合合并。C1-C5 环化的 1,4-双基产物经历内部 H 原子转移，并伴随着环外 CC 键的断裂。该序列提供了从烯炔获得苯并富烯的有效途径，并将自终止芳构化烯炔级联的效用扩展到光化学反应。这种自终止反应的关键特征是，尽管在关键环化步骤中涉及自由基物质，但不需要外部自由基源或猝灭剂来提供产物。在这些级联中，两个自由基中心都是瞬时形成的，并通过分子内氢转移和 CC 键断裂转化为闭壳产物。此外，将 CC 键裂解结合到烯炔的光化学自终止环化中为在有机合成中使用烯烃作为炔烃等价
• A novel C-H insertion via deoxygenation of amides by a Sm/SmI2 mixed system
  作者：Akiya Ogawa、Noriaki Takami、Taizoh Nanke、Syoji Ohya、Toshikazu Hirao、Noboru Sonoda

  DOI：10.1016/s0040-4020(97)00805-3

  日期：1997.9

  samarium/samarium diiodide mixed system successfully effects novel aminocyclopropanation and C-H insertion via the deoxygenation of amides. Styrenes undergo aminocyclopropanation by the reaction with aromatic amides, samarium metal, and samarium diiodide. Furthermore, the reaction of aliphatic amides with Sm/SmI2 in the presence of alkylbenzenes like toluene causes benzylic C-II insertion giving the corresponding

  mar /二碘化mixed混合系统可通过酰胺脱氧成功实现新型氨基环丙烷化和CH插入。苯乙烯通过与芳族酰胺，metal金属和二碘化sa的反应进行氨基环丙烷化。此外，在烷基苯如甲苯的存在下，脂族酰胺与Sm / SmI 2的反应导致苄基C-II插入，从而以高收率得到相应的苯乙胺衍生物。
• Color Change of Disperse Dyes on Nylon 6 Films with Dye Concentration
  作者：Takashi Nakamura、Takao Shibusawa

  DOI：10.1177/004051750007000908

  日期：2000.9

  decreasing Cf. This result is consistent with the sorption behavior of these dyes by nylon 6 film from water, where the dyes are sorbed by the polymer as two distinct species: L—species—dye taken up by the polymer through the Langmuir sorption mechanism, and P—species—dye taken up by Nemst-type partitioning. For both dyes, the relations between C f and the concentrations of species I and II are very

  研究了分散染料在尼龙 6 薄膜上的光谱随染料浓度 ( Cf ) 降低的变化。大多数偶氮分散染料的可见光吸收最大值 (λmax) 会随着 C f 的降低而移向更长的波长。对于具有由分子内电荷转移引起的偶极结构的染料，这种转变是显着的。根据麦克雷方程和因子分析，详细分析了 CI 分散橙 3 和 5（实用分散染料）的光谱变化。在低 Cf 范围内，这些染料在胶片上的 λmax 值比 McRae 方程估计的波长长得多，并且随着温度的升高而转移到更短的波长。因子分析结果表明，随着 Cf 降低，染色薄膜的可见吸收光谱可以描述为两个不同光谱的总和，指定为物种 I 和 II。物种 I 在比物种 II 更长的波长处具有 λmax。[species I]/[species II] 的比率随着 C f 的减小而增加，导致 λmax 随着 Cf 的减小而发生红移。该结果与尼龙 6 薄膜对水中的这些染料的吸附行为一致
• Facile Benzylic Alkylation of Arenes with Alcohols by Catalysis with Spirocyclic NHC Ir ^III Pincer Complex
  作者：Kun‐Long Dai、Qi‐Long Chen、Wen‐Ping Xie、Ka Lu、Zhi‐Bo Yan、Meng Peng、Chang‐Kun Li、Yong‐Qiang Tu、Tong‐Mei Ding

  DOI：10.1002/anie.202206446

  日期：2022.9.19

  A facile IrIII-catalyzed benzylic alkylation of arenes with alcohols has been accomplished via borrowing hydrogen (BH) pathways, and the newly developed spirocyclic NHC IrIII pincer complex (Cat A) serves as an efficient catalyst for this atom-economical and greener transformation. Some drug or bioactive molecules and functional material templates can be easily constructed by this strategy.

  通过借氢 (BH) 途径实现了一种简单的 Ir III催化的芳烃与醇的苄基烷基化，新开发的螺环 NHC Ir III钳形配合物 (Cat A) 可作为这种原子经济和绿色转化的有效催化剂. 一些药物或生物活性分子和功能材料模板可以通过这种策略轻松构建。