3-aza-9,10,11-trimethoxy-4-oxa-5-oxobenzacenaphthylene | 171925-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-aza-9,10,11-trimethoxy-4-oxa-5-oxobenzacenaphthylene
• 英文别名: 6,7,8-Trimethoxy-14-oxa-2-azatetracyclo[7.6.1.05,16.010,15]hexadeca-1,3,5(16),6,8,10(15),11-heptaen-13-one
• CAS: 171925-79-4
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: MEXMEXXVXUQNQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

反应信息

• 作为反应物：
  描述：

  6,6-二甲基-4,8-二氧杂螺[2.5]辛-1-烯 、 3-aza-9,10,11-trimethoxy-4-oxa-5-oxobenzacenaphthylene 在 吡啶 作用下， 以 氯仿 为溶剂， 25.0 ℃ 、1199.99 MPa 条件下， 反应 2.5h， 以36%的产率得到3-aza-3b-hydroxy-5-carboxyl-4-oxo-7,8,9-trimethoxy-3b,3c,4a,5-tetrahydro-4H-cyclopropano[f]benz[a]acenaphthylene lactone 2,2-dimethyl-1,3-propylene ketal
  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：

  8-bromo-5,6,7-trimethoxyisoquinoline 在 盐酸 、 氢氧化钾 、 lithium hydroxide 、 正丁基锂 、 potassium tert-butylate 、 乙酸酐 、 三氟乙酸 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 75.92h， 生成 3-aza-9,10,11-trimethoxy-4-oxa-5-oxobenzacenaphthylene
  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).