(Z)-(3-(2-iodovinyl)cycloprop-1-ene-1,2-diyl)dibenzene | 223248-78-0

• 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: (Z)-(3-(2-iodovinyl)cycloprop-1-ene-1,2-diyl)dibenzene
• 英文别名: Z-3-(2-iodoethenyl)cyclopropenes；(Z)-1,2-diphenyl-3-(2-iodoethenyl)-1-cyclopropene；(Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene；cis-1,2-diphenyl-3-(2-iodoetehnyl)cyclopropene；[3-[(Z)-2-iodoethenyl]-2-phenylcyclopropen-1-yl]benzene
• CAS: 223248-78-0
• 化学式: C₁₇H₁₃I
• 分子量: 344.195
• InChiKey: HOZIFVQJUYEYHN-QXMHVHEDSA-N

物化性质

• 熔点：
  74.2-75.6 °C
• 沸点：
  380.4±42.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (Z)-(3-(2-iodovinyl)cycloprop-1-ene-1,2-diyl)dibenzene 在 BuLi 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 cis-(Et3P)2Pt(Cl)(Z-CHCH-cyclo-C3HPh2)
  参考文献：
  名称：

  Rearrangement of a σ-2-(Cycloprop-2-enyl)vinyl- to an η³-Cyclopentadienylplatinum(II) Complex. Selective Protonolysis of the Platinum−Methyl Bond

  摘要：

  The sigma-2-(cycloprop-2-enyl)vinylplatinum(II) complex (PEt3)(2)Pt(Me)(CH=CH-cyclo-C3HPh2) (5) was prepared and characterized by NMR spectroscopy and X-ray crystallography. Treatment of 5 with Bronsted acids results in selective splitting of the Pt-methyl bond to give chloro derivative (PEt3)(2)Pt(Cl)(CH=CH-cyclo-C3HPh2) (6), or the rearranged eta(3)-diphenylcyclopentadienyl cation 7(+), depending on the acid employed. Formation of cation 7(+) could also be accomplished by treatment of 6 with TIPF6. Monitoring the protonolysis reactions by NMR spectroscopy at -60 degreesC, however, showed no evidence for platinabenzene or platinabenzvalene intermediates.

  DOI：

  10.1021/om0206507
• 作为产物：
  描述：

  ethyl 2,3-diphenylcycloprop-2-enecarboxylate 在 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (Z)-(3-(2-iodovinyl)cycloprop-1-ene-1,2-diyl)dibenzene
  参考文献：
  名称：

  ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

  摘要：

  一种有机发光器件（OLED），包括阳极、阴极和位于阳极和阴极之间的有机层。有机层包括一个包含配体LA的化合物，其中虚线代表与金属M的配位。金属M选自Os、Ru、Ir、Rh、Pt、Pd和Cu组，金属进一步与一个或多个配体LB配位，如果有多个配体LB，则这些配体LB可以相同或不同。可选地，一个或两个配体LB可以独立地通过R1至R5中的一个连接到配体LA。该发明还涉及一种包括OLED的消费产品，该OLED包括一个包含配体LA的化合物的有机层。

  公开号：

  US20190319198A1

文献信息

• Synthesis, Spectroscopy, and Structure of a Family of Iridabenzenes Generated by the Reaction of Vaska-Type Complexes with a Nucleophilic 3-Vinyl-1-cyclopropene
  作者：Robert D. Gilbertson、Thomas L. S. Lau、Seren Lanza、He-Ping Wu、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/om030394d

  日期：2003.8.1

  Seven new iridabenzenes were prepared by the addition of (Z)-1,2-diphenyl-3-(2-lithioethenyl)-1-cyclopropene to the Vaska-type complexes [IrCl(CO)(PR3)2], containing differing phosphine ligands. The iridabenzenes could be isolated from the reaction mixture either by direct means or after heating of the crude solution. In the case of the reactions using PMe3 and PEt3, a σ-vinyl/η2-cyclopropene Ir(I)

  通过在Vaska型络合物[IrCl（CO）（PR 3）2 ]中添加（Z）-1,2-二苯基-3-（2-硫代乙烯基）-1-环丙烯，制备了七个新的铱膦配体。可以通过直接方式或在加热粗溶液后从反应混合物中分离出铱苯。在使用PME的反应的情况下3和宠物3，一个σ乙烯基/η 2 -环丙烯的Ir（I）络合物，最好描述为一个iridabenzvalene，可以分离和完全表征。通过在溶液中加热，金属戊二烯中间体可以干净地转化为相应的铱苯。PEt 3用X射线晶体学表征取代的铱苯和iridabenzvalene。假定了从锂化的乙烯基环丙烯形成两个iridacycles以及将苯并戊烯异构化为苯的合理机理。
• Direct Synthesis of an Iridabenzene from a Nucleophilic 3-Vinyl-1-cyclopropene
  作者：Robert D. Gilbertson、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/ja984420o

  日期：1999.3.1
• Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics
  作者：Volker Jacob、Christopher W. Landorf、Lev N. Zakharov、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/om900439z

  日期：2009.9.14

  Lithium-halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (eta(4)-1,5-cod)PtCl2 yields the platinabenzene (eta(C5H3Ph2)-C-5)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (CP') unit are both derived from the cyclopropene skeleton. Starting instead with (eta(5)-C5Me5)Pt(CO)I, treatment with three nucleophilic (Z)-3-(2-lithiovinyl)cyclopropenes provides platinabenzenes (eta(5)-C5Me5)[PtC5H3PhR] (R = Ph (8), t-Bu (9), Me (10)) in low to modest yield. All platinaberizenes have been fully characterized by NMR spectroscopy and X-ray crystallography. Intermediate sigma-vinyl complexes (eta(5)-C5Me5)Pt(sigma-C5H3PhR) (R = Ph (14), t-Bu (15)) are also isolated from the reaction mixtures and convert cleanly to the corresponding platinaberizenes in near quantitative yield. Reactivity studies of (eta(5)-C5Me5)[PtC5H3Ph2] with a variety of reagents/conditions are also reported.
• Metallabenzenes and Valence Isomers. 5. Synthesis and Structural Characterization of a Rhodabenzvalene:  A Rare η²-Cyclopropene/σ-Vinylrhodium(I) Complex
  作者：He-Ping Wu、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/om020634+

  日期：2002.10.1

  Treatment of cis-1,2-diphenyl-3-(2-lithioethenyl)cyclopropene (2) with (Me3P)(2)Rh(CO)Cl gives the corresponding rhodabenzvalene 5, which contains rare eta(2)-cyclopropene and sigma-vinylic linkages to Rh. The successful preparation of this metallacycle can be attributed to the synergistic combination of intramolecular pi-bonding of the cyclopropene and sigma-vinylic linkage to the Rh atom, both of which in turn inhibit decomposition of the other respective moiety.