5-oxo-6-hydroxy-5H-cycloheptatrienoacenaphthylene | 171925-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-oxo-6-hydroxy-5H-cycloheptatrienoacenaphthylene
• 英文别名: 5-Hydroxytetracyclo[7.7.1.02,8.013,17]heptadeca-1(16),2,5,7,9,11,13(17),14-octaen-4-one
• CAS: 171925-76-1
• 化学式: C₁₇H₁₀O₂
• 分子量: 246.265
• InChiKey: NIXXUNKTTDXIIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

反应信息

• 作为反应物：
  描述：

  5-oxo-6-hydroxy-5H-cycloheptatrienoacenaphthylene 、 三甲基硅烷化重氮甲烷 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 96.0h， 生成 5-oxo-6-methoxy-5H-cycloheptatrienoacenaphthylene 、 6-oxo-5-methoxy-5H-cycloheptatrienoacenaphthylene
  参考文献：
  名称：

  Total Synthesis of Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine

  摘要：

  Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (1), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4 + 2] cycloaddition reaction of the alpha-pyrone 44 with the cyclopropenone ketal 18. Subsequent retro-Diels-Alder loss of CO2, norcaradiene rearrangement to the cycloheptatrienone ketal, and ketal hydrolysis provided the tropone 7 (granditropone). Regioselective hydroxylation of granditropone (NH2NH2; KOH) provided grandirubrine (1) and O-methylation of 1 provided both imerubrine (2) and isoimerubrine (3).

  DOI：

  10.1021/ja00155a009
• 作为产物：
  描述：

  1-苊酮 在 盐酸 、 氢氧化钾 、 lithium hydroxide 、 potassium tert-butylate 、 一水合肼 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， -78.0~100.0 ℃ 、1200.0 MPa 条件下， 反应 279.25h， 生成 5-oxo-6-hydroxy-5H-cycloheptatrienoacenaphthylene
  参考文献：
  名称：

  Total Synthesis of Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine

  摘要：

  Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (1), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4 + 2] cycloaddition reaction of the alpha-pyrone 44 with the cyclopropenone ketal 18. Subsequent retro-Diels-Alder loss of CO2, norcaradiene rearrangement to the cycloheptatrienone ketal, and ketal hydrolysis provided the tropone 7 (granditropone). Regioselective hydroxylation of granditropone (NH2NH2; KOH) provided grandirubrine (1) and O-methylation of 1 provided both imerubrine (2) and isoimerubrine (3).

  DOI：

  10.1021/ja00155a009

文献信息

• Total Synthesis of Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine
  作者：Dale L. Boger、Kanji Takahashi

  DOI：10.1021/ja00155a009

  日期：1995.12

  Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (1), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4 + 2] cycloaddition reaction of the alpha-pyrone 44 with the cyclopropenone ketal 18. Subsequent retro-Diels-Alder loss of CO2, norcaradiene rearrangement to the cycloheptatrienone ketal, and ketal hydrolysis provided the tropone 7 (granditropone). Regioselective hydroxylation of granditropone (NH2NH2; KOH) provided grandirubrine (1) and O-methylation of 1 provided both imerubrine (2) and isoimerubrine (3).