1,3-二苯基-2-甲基环丙烯 | 65102-39-8

• 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: 1,3-二苯基-2-甲基环丙烯
• 英文名称: 1,3-diphenyl-2-methylcyclopropene
• 英文别名: 1-methyl-2,3-diphenylcyclopropene；1,3-Diphenyl-2-methylcyclopropen；(2-methyl-3-phenylcyclopropen-1-yl)benzene
• CAS: 65102-39-8
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: QJIFBGAJQFDPOB-UHFFFAOYSA-N

物化性质

• 沸点：
  291.6±35.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1,3-二苯基-2-甲基环丙烯 在 trityl tetrafluoroborate 作用下， 以 叔丁醇 为溶剂， 生成 1-methyl-2,3-diphenylindene
  参考文献：
  名称：

  Mechanistic and exploratory organic photochemistry. 107. Vinylcyclopropene photochemistry: photochemistry applied to organic synthesis. Exploratory and mechanistic organic photochemistry

  摘要：

  DOI：

  10.1021/jo00402a003
• 作为产物：
  描述：

  (3,3-difluorocycloprop-1-ene-1,2-diyl)dibenzene 在 三乙基硼 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.0h， 生成 1,3-二苯基-2-甲基环丙烯
  参考文献：
  名称：

  宝石-二氟环丙烷衍生物的异常反应行为：β-单氟代烯丙基醇，醚，酯和酰胺的立体选择性合成

  摘要：

  上治疗宝石-difluorocyclopropylstannanes，从自由基hydrostannation衍生宝石在-78℃-difluorocyclopropenes，与THF中的1.5当量的MeLi的5分钟，然后进行骤冷与各种试剂，如H反应2 O，醇，羧酸酸，甲苯磺酰胺，相应的β-氟代烯丙基醇，醚，酯和酰胺，均具有可接受的收率，且具有独特的Z选择性。

  DOI：

  10.1021/ol5018596

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.
• Single-electron-transfer pathway in the coupling of cyclopropenyl cations with organometallic reagents
  作者：Albert Padwa、Steven I. Goldstein、Robert J. Rosenthal

  DOI：10.1021/jo00391a018

  日期：1987.7
• PADWA, ALBERT;GOLDSTEIN, STEVEN I.;ROSENTHAL, ROBERT J., J. ORG. CHEM., 52,(1987) N 15, 3278-3285
  作者：PADWA, ALBERT、GOLDSTEIN, STEVEN I.、ROSENTHAL, ROBERT J.

  DOI：——

  日期：——