1-(2,2-二苯基环丙基)-4-甲基苯 | 96010-03-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2,2-二苯基环丙基)-4-甲基苯
• 英文名称: (2-(p-tolyl)cyclopropane-1,1-diyl)dibenzene
• 英文别名: 1,1-diphenyl-2-(p-methylphenyl)cyclopropane；Benzene, 1-(2,2-diphenylcyclopropyl)-4-methyl-；1-(2,2-diphenylcyclopropyl)-4-methylbenzene
• CAS: 96010-03-6
• 化学式: C₂₂H₂₀
• 分子量: 284.401
• InChiKey: NLYSBTIPOLINGW-UHFFFAOYSA-N

物化性质

• 沸点：
  386.8±42.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  二苯甲酮 在 亚碘酰苯 、 对甲苯磺酸 、 一水合肼 、 nickel(II) hydroxide 作用下， 以 水 为溶剂， 反应 0.67h， 生成 1-(2,2-二苯基环丙基)-4-甲基苯
  参考文献：
  名称：

  的高价碘（III）氧化为重氮化合物和一锅镍（II）催化的环丙烷化

  摘要：

  描述了用未取代的酮对各种烯烃进行催化环丙烷化的一锅法。发现碘代苯（PhIO ）是到重氮化合物的有效氧化剂。选择Ni（OH）2作为有效且廉价的金属催化剂。在温和（80°C）和纯净的条件下，可以以中等到良好的收率（42–91％）有效地产生环丙烷产物（5分钟至4小时）。

  DOI：

  10.1039/c5nj02378e

文献信息

• Isolation and X-ray Crystal Structure of an Unusual Biscarbene Metal Complex and Its Reactivity toward Cyclopropanation and Allylic C−H Insertion of Unfunctionalized Alkenes
  作者：Yan Li、Jie-Sheng Huang、Zhong-Yuan Zhou、Chi-Ming Che

  DOI：10.1021/ja003184q

  日期：2001.5.1
• Half-sandwich ruthenium(II) complexes of aminophosphines: synthesis, structures and catalytic applications in C–C coupling reactions between styrenes and diphenyldiazomethane
  作者：Srinivasan Priya、Maravanji S. Balakrishna、Shaikh M. Mobin、Robert McDonald

  DOI：10.1016/j.jorganchem.2003.09.020

  日期：2003.12

  The half-sandwich Ru(II) complexes of the type [CpRu(PPh2N(H)R)(PPh3)Cl], [CpRu(PPh2N(H)R)(2)Cl] (R = Ph, C6H11) and [CpRu(PPh2N(R')PPh2-kappaP,kappaP)(PPh3)]Cl (R' = Et, Pr-n, Pr-i, Bu-n), were synthesized and the structures of complexes [CpRu(PPh2N(H)Ph)(PPh3)Cl] and [CpRu(PPh2N(H)Ph)(2)Cl] were confirmed by single crystal X-ray diffraction studies. All ruthenium complexes were employed in the cyclopropanation reaction of styrene derivatives in the presence of diphenyldiazomethane. All complexes afford 1,1,3,3-tetraphenyl cyclobutane along with cyclopropane derivatives; complex, [CpRu(PPh2N(Bu-n)PPh2-kappaP,kappaP)(PPh3)]Cl shows better selectivity in the formation of 1,1,2-triphenylcyclopropane. In all reactions appreciable amounts of cyclopropanation products and metathesis products, 1,2-diphenylcyclopropane and 1,1-diphenylethene were obtained along with 1,1,3-triphenylpropene derivatives. The variable temperature NMR studies have suggested that the cyclopropanation reactions in the presence of ionic complex, [CpRu(PPh2N(R')PPh2-kappaP,kappaP)(PPh3)]Cl proceeds via carbene intermediate, [CpRu(= CPh2)(Pph(2)N(R')PPh2-kappaP)(PPh3)]Cl. (C) 2003 Elsevier B.V. All rights reserved.
• Discrete Bridging and Terminal Copper Carbenes in Copper-Catalyzed Cyclopropanation
  作者：Xuliang Dai、Timothy H. Warren

  DOI：10.1021/ja047935q

  日期：2004.8.1

  The Cu(I) beta-diketiminate [Me2NN]Cu(eta(2)-ethylene) (2) catalyzes the cyclopropanation of styrene with N2CPh2 to give 1,1,2-triphenylcyclopropane in 67% yield. Addition of N2CPh2 to 2 equiv of 2 allows for the isolation of the dicopper carbene [Me2NN]Cu}(2)(mu-CPh2) (3) in which the diphenylcarbene moiety is symmetrically bound between two [Me2NN]Cu fragments (Cu-C = 1.922(4) and 1.930(4) Angstrom) with a Cu-Cu separation of 2.4635(7) Angstrom. In toluene-d(8) solution, 3 reversibly dissociates a [Me2NN]Cu fragment to give [Me2NN]Cu(toluene) and the terminal carbene [Me2NN]Cu=CPh2. Dicopper carbene 3 reacts with 3 equiv of styrene to give 1,1,2-triphenylcyclopropane and 2 equiv of [Me2NN]Cu(eta(2)-styrene) within minutes. DFT studies with simplified ligands indicate a stronger Cu-C pi-back-bonding interaction from two Cu(I) centers to the carbene acceptor orbital in a dicopper carbene than that present in a monocopper carbene. Nonetheless, the terminal carbene [Me3NN]Cu=CPh2 (8) that possesses a p-methyl group on each beta-diketiminato N-aryl ring may be isolated and exhibits a shortened Cu-C distance of 1.834(3) Angstrom. The stoichiometric cyclopropanation of styrene by 8 in 1,4-dioxane is first-order in both copper carbene 8 and styrene with activation parameters DeltaH(not similar or equal to) = 10.4(3) kcal/mol and DeltaS(not similar or equal to) = -32.3(9) cal/mol-K. In 1,4-dioxane, 8 decomposes to Ph2C=CPh2 via first-order kinetics with activation parameters DeltaH(not similar or equal to) = 21(1) kcal/mol and DeltaS(not similar or equal to) = -8(3) cal/mol-K. Arene solutions of thermally sensitive terminal carbene 8 decompose to [Me3NN]-Cu(arene), which reacts with 8 still present in solution to give the more thermally stable [Me3NN]Cu}(2)-(mu-CPh2).
• The philicity of a triplet carbene: additions of diphenylcarbene to styrene substrates
  作者：Hideo Tomioka、Kumiko Ohno、Yasuji Izawa、Robert A. Moss、Ramesh C. Munjal

  DOI：10.1016/s0040-4039(01)91299-7

  日期：1984.1