isoimerubrine | 74684-11-0

• 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: isoimerubrine
• 英文别名: 6,14,15,16-tetramethoxy-10-azatetracyclo[7.7.1.02,8.013,17]heptadeca-1(16),2(8),3,6,9,11,13(17),14-octaen-5-one
• CAS: 74684-11-0
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: LSZCTBVMSGTFLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isoimerubrine 、 sodium thiomethoxide 以 水 为溶剂， 反应 48.0h， 以1.5 mg的产率得到thioisoimerubrine
  参考文献：
  名称：

  Preparations and Antileukemic Activity of Congeners of Tropoloisoquinoline Alkaloids from Abuta concolor

  摘要：

  Antileukemic tropoloisoquinoline alkaloids, pareirubine A (1) and grandirubrine (2), at first have been isolated from Abuta concolor (Menispermaceae). Methylation of 1 and 2, existing in solution as a mixture of tautomers gave the corresponding four methyl derivatives (3 - 6). Thioimerubrine (7) and thioisoimerubrine (8) were prepared by the nucleophilic substitutions of the methoxyl groups at C-11 and -10, respectively. Acetylation of 1 and 2 produced the corresponding mono-acetyl tautomers (9 and 10). Antileukemic activity of these derived tropoloisoquinoline alkaloids is also reported.

  DOI：

  10.3987/com-93-s108
• 作为产物：
  描述：

  16-aza-10,11,12-trimethoxy-18-oxapentacyclo[7.7.1.1^2,6.0^2,8.0^13,17]octadeca-1(16),7,9(10),11,13(17),14-hexaen-4-one 在 甲醇 、 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 碘苯二乙酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 isoimerubrine
  参考文献：
  名称：

  Tropoloisoquinolines 的全合成：Imerubrine、Isoimerubrine 和 Grandirubrine1

  摘要：

  描述了对原异喹啉生物碱 imerubrine (1)、grandirubrine (2) 和 isoimerubrine (3) 的统一、方便的访问，并以乙炔连接的恶唑和 [4 + 3] 的分子内 Diels-Alder 反应的顺序应用为特征氧烯丙基的环加成。1 的区域选择性合成是通过使用 Moriarty 方法对 8-氧杂双环 [3.2.1]oct-6-en-3-one 环加合物进行立体和区域选择性氧化来实现的。这种环加成后官能化补充了α-烷氧基取代的氧烯丙基的合成效用，从而拓宽了氧烯丙基[4+3]环加成反应的范围。

  DOI：

  10.1021/ja0101072

文献信息

• Total Synthesis and Cytotoxicity Evaluation of Pareitropone and Analogues
  作者：Hyeonjeong Kim、Nara Shin、Suk-Koo Hong、Jongbeom Park、Sangkil Nam、David A. Horne、J. R. Choi、Jin Kun Cha、Young Gyu Kim

  DOI：10.1021/acs.joc.4c00236

  日期：——

  norcaradiene intermediate provides convenient access to highly condensed multicyclic tropones in high yields. This synthesis is modular, efficient, and scalable, highlighting the synthetic utility of radical anion coupling reactions in annulation reactions. This work is discussed in the context of total syntheses of the tropoloisoquinoline alkaloids. Also included are the preparation of several congeners and

  描述了通过酚类硝酸盐的氧化环化合成 pareitropone 的简明合成。使用 TMSOTf 作为添加剂以促进应变 norcaradiene 中间体的轻松形成，可以方便地以高产率获得高度浓缩的多环托油酮。这种合成是模块化的、高效的和可扩展的，突出了自由基阴离子偶联反应在环化反应中的合成效用。这项工作是在 tropolooisoquinoline 生物碱的完全合成的背景下讨论的。还包括几种同系物的制备及其生物活性的简要描述。
• 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).
• Menachery, Mary D.; Cava, Michael P., Heterocycles, 1980, vol. 14, # 7, p. 943 - 945
  作者：Menachery, Mary D.、Cava, Michael P.

  DOI：——

  日期：——
• Total Synthesis of Tropoloisoquinolines:  Imerubrine, Isoimerubrine, and Grandirubrine¹
  作者：Jae Chol Lee、Jin Kun Cha

  DOI：10.1021/ja0101072

  日期：2001.4.1

  ready access to the tropoloisoquinoline alkaloids imerubrine (1), grandirubrine (2), and isoimerubrine (3) is delineated and features sequential application of the intramolecular Diels-Alder reaction of an acetylene-tethered oxazole and the [4 + 3] cycloaddition of an oxyallyl. A regioselective synthesis of 1 was achieved by stereo- and regioselective oxidation of an 8-oxabicyclo[3.2.1]oct-6-en-3-one cycloadduct

  描述了对原异喹啉生物碱 imerubrine (1)、grandirubrine (2) 和 isoimerubrine (3) 的统一、方便的访问，并以乙炔连接的恶唑和 [4 + 3] 的分子内 Diels-Alder 反应的顺序应用为特征氧烯丙基的环加成。1 的区域选择性合成是通过使用 Moriarty 方法对 8-氧杂双环 [3.2.1]oct-6-en-3-one 环加合物进行立体和区域选择性氧化来实现的。这种环加成后官能化补充了α-烷氧基取代的氧烯丙基的合成效用，从而拓宽了氧烯丙基[4+3]环加成反应的范围。
• Preparations and Antileukemic Activity of Congeners of Tropoloisoquinoline Alkaloids from Abuta concolor
  作者：Hideji Itokawa、Kouji Matsumoto、Hiroshi Morita、Koichi Takeya

  DOI：10.3987/com-93-s108

  日期：——

  Antileukemic tropoloisoquinoline alkaloids, pareirubine A (1) and grandirubrine (2), at first have been isolated from Abuta concolor (Menispermaceae). Methylation of 1 and 2, existing in solution as a mixture of tautomers gave the corresponding four methyl derivatives (3 - 6). Thioimerubrine (7) and thioisoimerubrine (8) were prepared by the nucleophilic substitutions of the methoxyl groups at C-11 and -10, respectively. Acetylation of 1 and 2 produced the corresponding mono-acetyl tautomers (9 and 10). Antileukemic activity of these derived tropoloisoquinoline alkaloids is also reported.