1,1,2,2-tetraphenylcyclobutane | 84537-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1,2,2-tetraphenylcyclobutane
• 英文别名: Tetraphenylcyclobutane；(1,2,2-triphenylcyclobutyl)benzene
• CAS: 84537-61-1
• 化学式: C₂₈H₂₄
• 分子量: 360.499
• InChiKey: YCCFSWBVKIQEQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2,2,5,5-tetraphenyl-cyclopentanone 以 solid 为溶剂， 生成 1,1,2,2-tetraphenylcyclobutane
  参考文献：
  名称：

  Generation and Reactivity of a Triplet 1,4-Biradical Conformationally Trapped in a Crystalline Cyclopentanone

  摘要：

  DOI：

  10.1021/ja980112e

文献信息

• Photochemical electron-transfer reactions of 1,1-diarylethylenes
  作者：Susan L. Mattes、Samir. Farid

  DOI：10.1021/ja00283a034

  日期：1986.11

  constant for nucleophilic addition of methanol to 1a/sup .+/ is 1.6 x 10/sup 9/ M/sup -1/s/sup -1/; for addition to 1b/sup .+/ it is approx.10/sup 7/ M/sup -1/s/sup -1/. Methanol does not add efficiently to 1c/sup .+ / . Photooxygenation of the diarylethylene yields mainly the corresponding 3,3,6,6-tetraaryl-1,2-dioxane in a chain process. In the presence of methanol and oxygen, 1a yields mainly 1-hyd

  已经研究了由光激发的氰基蒽诱导的 1,1-二芳基乙烯 (1) 的二聚化、亲核加成和氧化反应。1,1-二苯基乙烯 (1a) 产生 2 + 2 和 2 + 4 环二聚体和一个脱氢二聚体，而 1,1-二苯甲基乙烯 (1b) 产生两个脱氢二聚体和 1,1-双（4-（二甲氨基）苯基）乙烯（ 1c) 不形成二聚体。脱氢二聚体的形成伴随着氰基蒽敏化剂的还原。对于 1b 的二聚化，可以通过添加醌来改变量子产率和产物比率。然后氢醌取代还原的敏化剂。甲醇亲核加成到 1a/sup.+/ 的反应常数为 1.6 x 10/sup 9/ M/sup -1/s/sup -1/；除了 1b/sup .+/ 它大约是 10/sup 7/ M/sup -1/s/sup -1/。甲醇不能有效地添加到 1c/sup 中。+ / 。二芳基乙烯的光氧化作用主要在链式过程中产生相应的 3,3,6,6-四芳基-1,2-二恶烷。在甲醇和氧气存在下，1a
• Direct observation and chemistry of biradicals from photochemical decarbonylation of .alpha.-perphenylated cycloalkanones
  作者：D. H. R. Barton、B. Charpiot、Keith U. Ingold、L. J. Johnston、W. B. Motherwell、J. C. Scaiano、S. Stanforth

  DOI：10.1021/ja00298a034

  日期：1985.6

  Chimie des diradicaux formes par la photolyse de la tetraphenyl-2,2,6,6 cyclohexanone et de la tetraphenyl-2,2,4,4 cyclopentanone

  Chimie des diradicaux formes par la photolyse de la tetraphenyl-2,2,6,6 cyclohexanone et de la tetraphenyl-2,2,4,4 cyclopentanone
• Photochemical Polar Addition of 1,1-Diphenylethene Using Photosensitive Surfactant in Stable Oil-in-Water Emulsion
  作者：Yasuharu Yoshimi、Michiya Higuchi、Tatsuya Itou、Minoru Hatanaka

  DOI：10.1246/cl.2004.1196

  日期：2004.9

  An aq NaOH solution of the photosensitive surfactant 1 was mixed with 1,1-diphenylethene 2 to form a stable oil-in-water emulsion and excitation of the emulsion afforded the alcohol 3 in good yield without stirring. The photosensitive surfactant 1 works more efficiently in heterogeneous system (in water) than in homogeneous system (in organic solvent).

  将光敏表面活性剂 1 的 NaOH 溶液与 1,1-二苯基噻吩 2 混合，形成稳定的水包油乳液，激发该乳液，无需搅拌即可得到醇 3，收率很高。光敏表面活性剂 1 在异构体系（水中）中比在均相体系（有机溶剂中）中更有效。
• Substituent-dependent electron-transfer-induced photooxygenation of 1,1-diarylethylenes
  作者：Klaus Gollnick、Albert Schnatterer、Gerald Utschick

  DOI：10.1021/jo00074a035

  日期：1993.10

  Rates and products of 9,10-dicyanoanthracene-sensitized photooxygenations of 1,1-diarylethylenes (1a-r) in acetonitrile were studied. If at least one of the aryl groups carries an electron-donating substituent at the para (or ortho) position (1a-1), 3,3,6,6-tetraaryl-1,2-dioxanes (2a-1) are generated in high yields (85-100%). Benzophenones (3) are the only other observable products. 1,1-Diphenylethylene (1n) and its m-methoxy (1m), p-chloro (1q,p), and p-nitro (1q,r) derivatives,however, yield mainly benzophenones (3m-r) (>50%) (the p-nitro compounds only in the presence of biphenyl). 1,2-Dioxanes (2m-p), cyclobutanes (4n-p), and alpha-tetralones (5m-o) are obtained as side products. Dioxanes, benzophenones, and alpha-tetralones are products of electron-transfer induced oxygenations involving triplet ground-state molecular oxygen, O-3(2). Singlet molecular oxygen, O2(1DELTA(g)),contributes to the benzophenone formation from strongly electron-donor substituted diarylethylenes. An exception is the most powerful electron-donor substituted diarylethylene 1a, with which O2(1DELTA(g)) undergoes an electron-transfer reaction affording dioxane 2a. Dioxane formation proceeds via free-radical cations 1.+, which enter into a chain reaction with 1, O-3(2), and another molecule of 1 to yield dioxane 2 and a new radical cation 1.+ that maintains the chain reaction. The efficiency of this chain process, however, is found to be several orders of magnitude smaller than expected. To explain this result, a 1,6-biradical.1-1-O2.is proposed to be generated in this chain reaction as the product-determining intermediate that predominantly fragments into O-3(2) and two molecules of 1. Cyclization to dioxane 2 and transformation to benzophenone 3 occur at presumably less than 0.1% from this biradical. The pathways leading to cyclobutanes (4) and alpha-tetralones (5) are also discussed.
• Photosensitized electron-transfer reactions. Interception of the geminate radical ion pair
  作者：Susan L. Mattes、Samir Farid

  DOI：10.1021/ja00343a061

  日期：1983.3