3-ethyl-1,2-diphenylindene | 89619-33-0

• 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: 3-ethyl-1,2-diphenylindene
• 英文别名: 1-ethyl-2,3-diphenylindene；1-Ethyl-2,3-diphenyl-1H-indene
• CAS: 89619-33-0
• 化学式: C₂₃H₂₀
• 分子量: 296.412
• InChiKey: KJVUKJOYQJEGFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-ethyl-1,2-diphenylindene 在 臭氧 作用下， 以 四氯化碳 为溶剂， 生成 (1R,8R,9R)-8-Ethyl-1,9-diphenyl-10,11,12-trioxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-triene 、 (1R,8S,9R)-8-Ethyl-1,9-diphenyl-10,11,12-trioxa-tricyclo[7.2.1.0^2,7]dodeca-2(7),3,5-triene
  参考文献：
  名称：

  一系列 1-取代茚的臭氧分解。取代基空间位阻对臭氧化物外/内比的影响

  摘要：

  Ozonolyse d'une serie d'indenes dissubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4

  DOI：

  10.1021/ja00322a032
• 作为产物：
  描述：

  2,3-diphenyl-indan-1-one 、 乙基溴化镁 在 氢碘酸 作用下， 以 溶剂黄146 为溶剂， 生成 3-ethyl-1,2-diphenylindene
  参考文献：
  名称：

  一系列 1-取代茚的臭氧分解。取代基空间位阻对臭氧化物外/内比的影响

  摘要：

  Ozonolyse d'une serie d'indenes dissubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4

  DOI：

  10.1021/ja00322a032

文献信息

• 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
• 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.
• MIURA, MASAHIRO;NOJIMA, MASATOMO;KUSABAYASHI, SHIGEKAZU;MCCULLOUGH, K. J., J. AMER. CHEM. SOC., 1984, 106, N 10, 2932-2936
  作者：MIURA, MASAHIRO、NOJIMA, MASATOMO、KUSABAYASHI, SHIGEKAZU、MCCULLOUGH, K. J.

  DOI：——

  日期：——
• Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios
  作者：Masahiro Miura、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/ja00322a032

  日期：1984.5

  Ozonolyse d'une serie d'indenes disubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4

  Ozonolyse d'une serie d'indenes dissubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4