4-Isopropyl-2,3-diphenyl-naphthalen-1-ol | 108695-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Isopropyl-2,3-diphenyl-naphthalen-1-ol
• 英文别名: 2,3-Diphenyl-4-propan-2-ylnaphthalen-1-ol；2,3-diphenyl-4-propan-2-ylnaphthalen-1-ol
• CAS: 108695-35-8
• 化学式: C₂₅H₂₂O
• 分子量: 338.449
• InChiKey: QFTGSDPDQIQSGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-Isopropyl-2,3-diphenyl-naphthalen-1-ol 、 碘甲烷 在 sodium hydroxide 、 苄基三乙基碘化铵 作用下， 以 二氯甲烷 为溶剂， 生成 2,3-diphenyl-1-methoxy-4-(1-methylethyl)naphthalene
  参考文献：
  名称：

  Metal-Catalyzed Cyclopropene Rearrangements for Benzannulation: Evaluation of an Anthraquinone Synthesis Pathway and Reevaluation of the Parallel Approach via Carbene-Chromium Complexes

  摘要：

  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.

  DOI：

  10.1021/ja00095a014
• 作为产物：
  描述：

  3-isopropyl-1,2,3-triphenylcyclopropene 、 alkaline earth salt of/the/ methylsulfuric acid 以 1,4-二氧六环 为溶剂， 反应 7.5h， 以8%的产率得到4-Isopropyl-2,3-diphenyl-naphthalen-1-ol
  参考文献：
  名称：

  Metal carbonyl-promoted rearrangement of cyclopropenes to naphthols

  摘要：

  DOI：

  10.1021/ja00248a047

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.