2,3,4-triphenyl-1-naphthol | 2892-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,4-triphenyl-1-naphthol
• 英文别名: 2,3,4-Triphenylnaphthalen-1-ol
• CAS: 2892-40-2
• 化学式: C₂₈H₂₀O
• 分子量: 372.466
• InChiKey: LUNGAAPOKAJZFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,4-triphenyl-1-naphthol 、 乙酸酐 在 硫酸 作用下， 生成 acetic acid-(2,3,4-triphenyl-[1]naphthyl ester)
  参考文献：
  名称：

  The Reaction between Lithium and Diphenylacetylene

  摘要：

  DOI：

  10.1021/ja01850a006
• 作为产物：
  描述：

  4-benzoyl-2,3,4-triphenyl-4H-1-naphthone 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以64%的产率得到2,3,4-triphenyl-1-naphthol
  参考文献：
  名称：

  Phototransformations of epoxyindanone adducts. Steady-state and laser flash photolysis studies

  摘要：

  DOI：

  10.1021/jo00382a020

文献信息

• Studies on the Tandem Reaction of 4-Aryl-2,3-allenoates with Organozinc Reagents: A Facile Route to Polysubstituted Naphthols
  作者：Guobi Chai、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1002/chem.200901779

  日期：2009.10.26

  Diversified polysubstituted α‐naphthols have been efficiently constructed through a tandem reaction of easily available 2,3‐allenoates and organozinc reagents in moderate to excellent yields (see scheme). Some of the products may undergo a couple of sequential coupling reactions to afford polysubstituted naphthalenes.

  通过容易获得的2,3-烯丙酸酯和有机锌试剂的串联反应，以中等至极好的收率串联反应，可以有效地构建多样化的多取代α-萘酚（参见方案）。一些产物可能会经历几次顺序的偶联反应，以提供多取代的萘​​。
• Cyclopropene Derivatives. II. The Reaction of Diazoketone with Triple Bond
  作者：Naruyoshi Obata、Ichiro Moritani

  DOI：10.1246/bcsj.39.1975

  日期：1966.9

  additions of some keto-carbene to a triple bond were studied. Since keto-carbene rearranges easily to a ketene derivative (Wolff rearrangement), the carbenic addition will always be in competition with the rearrangement. In the case of benzoylphenylcabene, the rearrangement is preferred, and no cyclopropene derivative is obtained. However, benzoyl and acetylcarbene, both having hydrogen instead of

  研究了将一些酮卡宾加成到三键上。由于酮卡宾很容易重排为酮烯衍生物（沃尔夫重排），因此卡宾加成总是与重排竞争。在苯甲酰苯基卡宾的情况下，重排是优选的，并且没有得到环丙烯衍生物。然而，苯甲酰基和乙酰卡宾都具有氢而不是苯基作为取代基，可以成功地与二苯基乙炔和二正丁基乙炔加成，从而得到 1, 2-二取代的环丙烯衍生物。因此，发现酰基环丙烯通过利用酮卡宾与三键的卡宾加成在一步中合成。
• 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.