1,1,2-三苯基-2-甲基环丙烷 | 32266-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,1,2-三苯基-2-甲基环丙烷
• 英文名称: 1-methyl-1,2,2-triphenylcyclopropane
• 英文别名: (1-Methyl-2,2-diphenylcyclopropyl)benzene
• CAS: 32266-22-1
• 化学式: C₂₂H₂₀
• 分子量: 284.401
• InChiKey: DXGAQACDPGZGLI-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  373.1±42.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,1,2-三苯基-2-甲基环丙烷 在 nitrosonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 、
  参考文献：
  名称：

  通过 1,1,2,2-四取代环丙烷与 NOBF4 反应形成 2-取代 2-异恶唑啉盐

  摘要：

  1,1,2,2-四苯基-和1-甲基-1,2,2-三苯基环丙烷与NOBF4反应，通过苯基从3-苯基-2-迁移得到2-苯基-2-异恶唑啉鎓四氟硼酸盐异恶唑啉鎓或 1-异恶唑啉鎓中间体。

  DOI：

  10.1246/cl.1989.457
• 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 4.0h， 生成 1,1,2-三苯基-2-甲基环丙烷
  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

• Reactions of Ferrocenylcarbene. III. The Addition Reactions of Some α-Ferrocenylcarbenes to 1,1-Diphenylethylene
  作者：Akio Sonoda、Ichiro Moritani

  DOI：10.1246/bcsj.43.3522

  日期：1970.11

  lowest reactivity in addition reactions to the olefin. It has been established by a study of the NMR spectra that, in the ferrocenylcyclopropanes only, there is a restricted rotation about the bond between ferrocenyl and cyclopropyl groups. On this basis, the reactivity of the ferrocenylcarbenes has been discussed in terms of the steric hindrance of the bulky ferrocenyl group.

  通过相应酰基二茂铁甲苯磺腙钠盐的热分解，研究了 α-二茂铁基卡宾（二茂铁基、二茂铁基甲基和二茂铁基苯基卡宾）与 1,1-二苯基乙烯的加成反应。然后，将二茂铁基卡宾的反应性与相应的苯基和对茴香基卡宾的反应性进行了比较。已经发现，在所研究的卡宾中，二茂铁基卡宾在与烯烃的加成反应中表现出最低的反应性。通过对 NMR 光谱的研究已经确定，仅在二茂铁基环丙烷中，二茂铁基和环丙基之间的键的旋转受限。在此基础上，已经根据庞大的二茂铁基团的空间位阻讨论了二茂铁基卡宾的反应性。
• Iron/N-doped graphene nano-structured catalysts for general cyclopropanation of olefins
  作者：Abhijnan Sarkar、Dario Formenti、Francesco Ferretti、Carsten Kreyenschulte、Stephan Bartling、Kathrin Junge、Matthias Beller、Fabio Ragaini

  DOI：10.1039/d0sc01650k

  日期：——

  The first examples of heterogeneous Fe-catalysed cyclopropanation reactions are presented. Pyrolysis of in situ-generated iron/phenanthroline complexes in the presence of a carbonaceous material leads to specific supported nanosized iron particles, which are effective catalysts for carbene transfer reactions. Using olefins as substrates, cyclopropanes are obtained in high yields and moderate diastereoselectivities

  介绍了非均相 Fe 催化的环丙烷化反应的第一个例子。在含碳材料的存在下原位生成的铁/菲咯啉配合物的热解产生特定的负载纳米铁颗粒，这是卡宾转移反应的有效催化剂。使用烯烃作为底物，以高产率和中等非对映选择性获得环丙烷。所开发的协议是可扩展的，并且在温和条件下使用氧化再活化协议可以有效地恢复失活后回收催化剂的活性。
• 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
• Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies
  作者：Kazuhiko Mizuno、Nobuyuki Ichinose、Toshiyuki Tamai、Yoshio Otsuji

  DOI：10.1021/jo00043a026

  日期：1992.8

  The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields. The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in CH3CN also afforded 2a-d or 2a-b. These reactions proceed via the attack of NO on the radical cation of 1, which is formed by electron transfer from 1 to 1DCA* or NO+. The reaction of 1-alkyl-2-arylcyclopropanes with NOBF4 afforded mixtures of 3-alkyl-5-aryl-2-isoxazolines and 4-alkyl-5-aryl-2-isoxazolines via the direct attack of NO+ on the cyclopropane rings. The reaction of 1,1,2,2-tetraphenylcyclopropane with NOBF4 afforded 2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate via the migration of the phenyl group to nitrogen.
• 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.