3-methyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine | 42382-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-methyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine
• 英文别名: 3-methyl-6,7-dihydro-1H-indeno[6,7,1-def]cinnoline；3-methyl-1H-acenaphtho[5,6-de]pyridazine；3-methyl-1H-acenaphtho[5,6]pyridazine；3-methylaceperidazine；3-methyl-6,7-dihydro-1H-indeno[6,7,1-def]cinnoline；7-methyl-5,6-diazatetracyclo[6.5.2.04,15.011,14]pentadeca-1,3,6,8(15),9,11(14)-hexaene
• CAS: 42382-42-3
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: FMKISHYMYQSBQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  404.0±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine 在 nitronium tetrafluoborate 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以59%的产率得到3-methyl-9-nitro-1H-indeno[6,7,1-def]cinnoline
  参考文献：
  名称：

  Nitration of 3-methyl-6,7-dihydro-1H-indeno[6,7,1-def]cinnoline and its N-substituted derivatives

  摘要：

  The nitration of 3-methylaceperidazine (3-methyl-6,7-dihydro-1H-indeno[6,7,1-def]cinnoline) and its N-substituted derivatives with nitric acid of different concentrations requires harsh conditions and is accompanied by dehydrogenation and dimerization of the initial compound.

  DOI：

  10.1134/s1070428017070193
• 作为产物：
  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

文献信息

• 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。
• Nitration of 3-Methylaceperidazines with a Large Excess of Fuming Nitric Acid
  作者：N. I. Omelichkin、L. G. Minyaeva、A. A. Milov、L. G. Kuz’mina、V. V. Mezheritskii

  DOI：10.1134/s1070428018080146

  日期：2018.8

  Nitration of N-acetyl-3-methylaceperidazine with a 2–3-fold excess of nitric acid (d 1.36, 1.48) in glacial acetic acid results in the exclusive formation of mono- and dinitroderivatives. The nitration of 3-methylaceperidazine and its N-alkyl- and N-acetyl-substituted derivatives with a 6–9-fold excess of fuming nitric acid (d 1.54) in the same conditions results in the formation of both the expected

  用冰醋酸中的2–3倍过量的硝酸（d 1.36、1.48）硝化N-乙酰基-3-甲基乙酰哌嗪会导致一硝基和二硝基衍生物的排他性形成。在相同条件下用6-9倍过量的发烟硝酸（d 1.54）硝化3-甲基乙酰哌嗪及其N-烷基和N-乙酰基取代的衍生物会导致两种预期的单-硝化作用，以及硝化作用和硝酸的亲电子加成产物，该硝化产物分子的molecule骨架具有双键。
• Alkylation of 3-methyl-1H-acenaphtho[5,6-de]pyridazine
  作者：N. I. Omelichkin、L. G. Minyaeva、V. V. Mezheritskii

  DOI：10.1134/s1070428017020208

  日期：2017.2

  Alkylation of 3-methyl-1H-acenaphtho[5,6]pyridazine with methyl and propyl iodides as well as with benzyl chloride in alkaline medium leads to the formation of the corresponding both N- and C-substituted pyridazine derivatives and also to the dimerization product of the initial compound. The ratio of obtained compounds depends on the used hydride, reaction temperature, and solvent.
• 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.