5-acetyl-6-hydroxyacenaphthene | 140172-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-acetyl-6-hydroxyacenaphthene
• 英文别名: 1-(6-hydroxyacenaphthen-5-yl)ethanone；1-(6-hydroxy-1,2-dihydroacenaphthylen-5-yl)ethanone
• CAS: 140172-82-3
• 化学式: C₁₄H₁₂O₂
• mdl: MFCD02943234
• 分子量: 212.248
• InChiKey: WKQXQXDJRLCOTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: ethanol (64-17-5))
• 沸点：
  440.8±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-6-hydroxyacenaphthene 在 一水合肼 作用下， 反应 0.08h， 以96%的产率得到3-methyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine
  参考文献：
  名称：

  1H-1,2-二氮杂苯萘与脂肪族羧酸酐的酰化

  摘要：

  DOI：

  10.1134/s1070428016010255
• 作为产物：
  描述：

  1-(6-aminoacenaphthen-5-yl)ethanone 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.33h， 以70%的产率得到5-acetyl-6-hydroxyacenaphthene
  参考文献：
  名称：

  Mezheritskii, V. V.; Pikus, A. L.; Tregub, N. G., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, p. 1945 - 1950

  摘要：

  DOI：

文献信息

• New synthetic approach to peri-hydroxy-substituted carbonyl acenaphthene derivatives
  作者：A. N. Bezuglov、L. G. Minyaeva、V. V. Mezheritskii

  DOI：10.1134/s107042800803007x

  日期：2008.3

  A new approach to the synthesis of peri-hydroxyacenaphthoyl compounds has been developed on the basis of acylation (formylation) of 5-acyloxyacenaphthenes. The reactions are accompanied by formation of the corresponding 3- and 8-acyl-substituted isomers. In some cases, the latter can be isolated and identified by 1H NMR spectroscopy.

  在 5-乙酰氧基苊的酰化（甲酰化）基础上，开发出了一种合成过羟基苊酰化合物的新方法。这些反应伴随着相应的 3-酰基和 8-酰基取代异构体的形成。在某些情况下，可以通过 1H NMR 光谱分离和鉴定后者。
• Pyran derivatives peri-fused to acenaphthene and acenaphthylene
  作者：I. A. Abdulaeva、L. G. Minyaeva、V. V. Mezheritskii

  DOI：10.1134/s1070428011030109

  日期：2011.3

  reacted with sodium methoxide to give 2-acyl-3-hydroxyacenaphtho[5,6-bc]pyran derivatives, while their reaction with piperidine afforded acenaphtho[5,6-bc]pyran-3-on. Heating of the latter in acetic anhydride produced 3-acetoxyacenaphtho[5,6-bc]pyran which was subjected to dehydrogenation to obtain a new heteroaromatic system. DOI

  围-Acyloxyacenaphthenyl溴甲基通过溴化制备酮围-acyloxyacenaphthenyl甲基酮用甲醇钠反应，得到2-酰基-3- hydroxyacenaphtho [5,6- BC ]吡喃衍生物，而它们与哌啶反应，得到苊并[5,6- BC ] pyran-3-on。后者在乙酸酐中加热产生3-乙酰氧基ac [5,6- bc ]吡喃，将其脱氢以获得新的杂芳族体系。土井
• Synthesis of new 1H-pyridazine derivatives peri-annelated with acenaphthene and acenaphthylene
  作者：V. V. Mezheritskii、L. G. Minyaeva、R. V. Tyurin

  DOI：10.1007/s11172-005-0322-4

  日期：2005.3

  The reaction of 6-acetyl-5-hydroxyacenaphthene with methylhydrazine afforded 1,3-dimethyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine. Its dehydrogenation with chloranil gave 1,3-dimethyl-1H-acenaphtho[5,6-de]pyridazine, which is a heteroaromatic compound with an essentially new topology of the ρsystem. The reaction of 3-methyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine with 3,5-di-tert-butyl-1,2-benzoquinone

  6-乙酰基-5-羟基苊与甲基肼反应得到1,3-二甲基-1H-6,7-二氢苊并[5,6-脱]哒嗪。其与氯苯醌脱氢得到 1,3-二甲基-1H-苊并[5,6-de]哒嗪，这是一种杂芳族化合物，具有全新的 ρ 系统拓扑结构。3-甲基-1H-6,7-二氢苊并[5,6-脱]哒嗪与 3,5-二叔丁基-1,2-苯醌反应生成含有苊和苊部分的二聚体。在 1' 和 9 位连接的退火 1H-1,2-二嗪。
• Protonation, deuteration, and formylation of aceperidazylenes
  作者：V. V. Mezheritskii、L. G. Minyaeva、N. I. Omelichkin、A. A. Milov、K. A. Lysenko、A. F. Smolyakov

  DOI：10.1134/s107042801407015x

  日期：2014.7

  1H-1,2-Diazaphenalene derivatives in which the pyridazine ring is ortho- and peri-fused to acenaphthene and acenaphthylene (1H-indeno[6,7,1-def]cinnolines) have been synthesized. It has been found that electrophilic attack on these compounds is directed at C-6.
• Oxidative transformations of peridazines
  作者：V. V. Mezheritskii、L. G. Minyaeva、O. M. Golyanskaya、R. B. Tyurin、O. Ya. Borbulevich、G. S. Borodkin、A. N. Antonov

  DOI：10.1134/s1070428002120229

  日期：2006.2

  Reactions of peridazines (1H-1,2-diazaphenalenes) with electron-donor reagents (quinones, potassium ferrocyanide) involve multistage oxidative transformations resulting in products of dimarization and (or) dehydration.