9-戊基蒽 | 33576-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-戊基蒽
• 英文名称: 9-n-pentylanthracene
• 英文别名: 9-Pentylanthracene
• CAS: 33576-54-4
• 化学式: C₁₉H₂₀
• 分子量: 248.368
• InChiKey: ZSKMTKFEJPCWSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  N-乙基甲酰苯胺 、 9-戊基蒽 在 邻二氯苯 、 三氯氧磷 作用下， 生成 10-pentyl-anthracene-9-carbaldehyde
  参考文献：
  名称：

  Martin; Van Hove, Bulletin des Societes Chimiques Belges, 1952, vol. 61, p. 504,511

  摘要：

  DOI：
• 作为产物：
  描述：

  9-氯甲基蒽 在 四甲基乙二胺 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 3.25h， 生成 9-戊基蒽
  参考文献：
  名称：

  Preparative Methodology and Pyrolytic Behavior of Anthrylmonocarbenes:  Synthesis and Chemistry of 1H-Cyclobuta[de]anthracene

  摘要：

  This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)-[methoxy(trimethylsilyl)methyl] anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(l0)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. alpha-Methoxy-9-anthrylmethyllithium (1), prepared from 9-(methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10-dihydro-9-(methoxymethylene)-10-substituted- anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t-BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9-(trimethylsilyloxymethyl)-anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash-vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10-[methoxy(trimethylsilyl)methyl]anthracene (55) at 650 degrees C/10(-3) mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10-deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C-10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by Clo-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10-dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).

  DOI：

  10.1021/jo981105b

文献信息

• Flexible and Practical Synthesis of Anthracenes through Gold-Catalyzed Cyclization of<i>o</i>-Alkynyldiarylmethanes
  作者：Chao Shu、Cheng-Bin Chen、Wei-Xi Chen、Long-Wu Ye

  DOI：10.1021/ol402713g

  日期：2013.11

  A concise gold-catalyzed method for the preparation of anthracenes from o-alkynyldiarylmethanes has been developed. Under mild reaction conditions, versatile anthracene derivatives were formed in moderate to good yields. The high flexibility, broad substrate scope, and mild nature of this reaction render it a viable alternative for the synthesis of anthracenes.
• Griendt, Freek van de; Cerfontain, Hans, Journal of the Chemical Society. Perkin transactions II, 1980, p. 13 - 18
  作者：Griendt, Freek van de、Cerfontain, Hans

  DOI：——

  日期：——
• GRIENDT F.; CERFONTAIN H., PHOSPH. AND SULFUR, 1979, 6, NO 1-2, 109
  作者：GRIENDT F.、 CERFONTAIN H.

  DOI：——

  日期：——