1,2,3-三苯基-3-乙烯基-1-环丙烯 | 62747-62-0

• 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: 1,2,3-三苯基-3-乙烯基-1-环丙烯
• 英文名称: 1,2,3-triphenyl-3-vinyl-1-cyclopropene
• 英文别名: triphenylvinylcyclopropene；1,2,3-Triphenyl-3-vinylcyclopropen；1,2,3-Triphenyl-3-vinyl-cyclopropene；(1-ethenyl-2,3-diphenylcycloprop-2-en-1-yl)benzene
• CAS: 62747-62-0
• 化学式: C₂₃H₁₈
• 分子量: 294.396
• InChiKey: YMXDJWYBTXXWBM-UHFFFAOYSA-N

物化性质

• 沸点：
  375.1±42.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  1,2,3-三苯基-3-乙烯基-1-环丙烯 在 copper octadecanoate 作用下， 以 环己烷 为溶剂， 反应 0.08h， 以96%的产率得到1,2,3-triphenylcyclopentadiene
  参考文献：
  名称：

  Domnin, I. N.; Plotkin, V. N.; Komendantov, M. I., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 10, p. 2034 - 2036

  摘要：

  DOI：
• 作为产物：
  描述：

  乙烯基溴化镁 、 1,2,3-triphenylcyclopropenylium perchlorate 生成 1,2,3-三苯基-3-乙烯基-1-环丙烯
  参考文献：
  名称：

  Photochemical transformations of small ring compounds. 95. The problem of regioselectivity in the photochemical ring-opening reaction of 3-phenyl- and 3-vinyl-substituted cyclopropenes to indenes and 1,3-cyclopentadienes

  摘要：

  DOI：

  10.1021/jo00402a002

文献信息

• Stepwise transition metal promoted ring expansion reactions of vinylcyclopropenes to give cyclopentadienes and cyclohexa-2,4-dienones. The first example of a 1-metallacyclohexa-2,4-diene complex, {[Pt–CH₂–CHC(Ph)–C(Ph)C(Ph)](PPh₃)₂}
  作者：Norman A. Grabowski、Russell P. Hughes、B. Scott Jaynes、Arnold L. Rheingold

  DOI：10.1039/c39860001694

  日期：——

  rop-1-ene (1) reacts with [Pt(η2-C2H4)(PPh3)2] to give the first example of a 1-platinacyclohexa-2,4-diene complex (2)(the crystal structure of which has been determined), with [Rh(η5-C9H7)(η-C2H4)2] to give the η4-cyclopentadiene compound (3), and with [Fe2(CO)9] to give the η4-cyclohexa-2,4-dienone complex (5); on heating, the metallacyclohexadiene (2) reductively eliminates 1,2,3-triphenylcyclopentadiene

  1,2,3-三苯基-3- vinylcycloprop -1-烯（1）反应以[PT（η 2 -C 2 H ^ 4）（PPH 3）2 ]，得到第一1- platinacyclohexa-2的实例中，雄甾-1,4-二烯配合物（2）（晶体其结构已被确定）中，用的[Rh（η 5 -C 9 ħ 7）（η-C 2 H ^ 4）2 ]，得到η 4环戊二烯化合物（3）中，用的[Fe 2（CO）9 ]，得到η 4 -环己-2,4-二烯酮络合物（5）; 在加热时，金属环己二烯（2）还原性地消除1,2,3-三苯基环戊二烯。
• Metal carbonyl-promoted rearrangement of cyclopropenes to naphthols
  作者：M. F. Semmelhack、Suzzy Ho、Michael Steigerwald、M. C. Lee

  DOI：10.1021/ja00248a047

  日期：1987.7
• Iridium-Promoted Reactions of Carbon−Carbon Bonds. Skeletal Rearrangement of a Vinylcyclopropene during Iridacyclohexadiene Formation and Subsequent Isomerization of Iridacyclohexadienes via α,α‘-Substituent Migrations
  作者：Russell P. Hughes、Hernando A. Trujillo、James W. Egan、Arnold L. Rheingold

  DOI：10.1021/ja992407d

  日期：2000.3.1

  On treatment with [Ir(PMe3)(2)(acac)] at room temperature, 1,2,3-triphenyl-3-vinylcyclopropene undergoes ring opening accompanied by rearrangement to give, instead of the expected 1,2,3-triphenyliridacyclohexadiene complex, a crystallographically characterized 1,2,4-triphenyliridacyclohexadiene complex containing cis-phosphine ligands. Studies with H-2- and doubly C-13-labeled vinylcyclopropenes, the syntheses and characterization of which are also reported, show that this process involves a rearrangement of the carbon skeleton and not a substituent shift. The corresponding 1,2-diphenyl-3-vinylcyclopropene undergoes iridacyclohexadiene formation without any rearrangement. On heating at 90 degrees C, each iridacycle converts to its corresponding isomer containing trans-phosphine ligands without any skeletal or substituent rearrangement of the metallacycle, as evidenced by absence of change in the labeling pattern. At higher temperatures, further rearrangement occurs in the case of each metallacycle, which does not alter the metallacyclohexadiene backbone, but rather exchanges the substituents of the alpha and alpha' carbon atoms. This rearrangement is shown to occur even when there is no driving force due to relief of steric effects. Mechanisms for each rearrangement are proposed and discussed.
• Mechanistic and exploratory organic photochemistry. 107. Vinylcyclopropene photochemistry: photochemistry applied to organic synthesis. Exploratory and mechanistic organic photochemistry
  作者：Howard E. Zimmerman、Steven M. Aasen

  DOI：10.1021/jo00402a003

  日期：1978.4
• Metal-Catalyzed Cyclopropene Rearrangements for Benzannulation: Evaluation of an Anthraquinone Synthesis Pathway and Reevaluation of the Parallel Approach via Carbene-Chromium Complexes
  作者：M. F. Semmelhack、Suzzy Ho、D. Cohen、M. Steigerwald、M. C. Lee、G. Lee、Adam M. Gilbert、William D. Wulff、Richard G. Ball

  DOI：10.1021/ja00095a014

  日期：1994.8

  The reaction of 3-arylcyclopropenes with Cr(CO)(6) and Mo(CO)(6) produces naphthols, in an example of metal-promoted benzannulation. Substituents at C-3 (in addition to aryl) have a strong effect on the success of the process: 3-H derivatives are generally effective, but the yields decrease for 3-alkyl derivatives as the size of the alkyl group increases. The 3,3-diphenyl and 3-cyano derivatives are unreactive. The mechanism is postulated to involve metal-complexed vinyl carbene units, parallel with the benzannulation reaction involving arylcarbene complexes with alkynes. The regioselectivity has been probed with various unsymmetrically 1,2-disubstituted 3-arylcyclopropenes. The results suggest a simple correlation with steric size, consistent with initial cleavage of the cyclopropene sigma bond bearing the smaller substituent. The result of this regioselectivity is a product structure showing a substituent arrangement opposite to that from the carbene-chromium approach; the smaller substituent of the cyclopropyl double bond ends up adjacent to the phenol OH in the product. Catalytic activity at low efficiency was observed, using a Mo(CO)a catalyst. However, the use of Mo(CO)(6) also promotes formation of indenes as significant byproducts at the expense of naphthalenes. Attempts to use the arylcyclopropene rearrangement to convert a 3-(1,4-dimethoxy-2-naphthyl)cyclopropene to an anthraquinone skeleton produced instead a phenanthrene via an unusual substitution for a methoxy substituent. A related example previously reported to produce anthraquinones via the naphthylcarbene-chromium/ alkyne reaction was shown to be in error; the correct structure is again a phenanthrone, and the product is exactly parallel with that observed in the cyclopropene rearrangement. A naphthoquinone substituted with a cyclopropene at C-2 does provide the first example of metal-promoted benzannulation to give an anthraquinone.