13a-hydroxy-10,11-dimethoxy-7,8,13,13a-tetrahydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5,13-dione | 113557-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 13a-hydroxy-10,11-dimethoxy-7,8,13,13a-tetrahydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5,13-dione
• 英文别名: 8,14-dioxo-13-hydroxyaporhoeadane；7,8-dihydro-13a-hydroxy-10,11-dimethoxy-5H-isoindolo<1,2-b><3>benzazepin-5,13aH-dione；7,8-dihydro-13a-hydroxy-10,11-dimethoxy-5H-isoindolo[1,2-b][3]benzazepine-5,13(13aH)-dione；13a-Hydroxy-10,11-dimethoxy-7,8-dihydroisoindolo[2,1-c][3]benzazepine-5,13-dione
• CAS: 113557-29-2
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: ASIDMLZQDANSRE-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  615.3±55.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 在 sodium hydroxide 、 N-氯代丁二酰亚胺 、 三氟化硼乙醚 、 silver nitrate 作用下， 以 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 1.5h， 生成 13a-hydroxy-10,11-dimethoxy-7,8,13,13a-tetrahydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5,13-dione
  参考文献：
  名称：

  光环化在金刚烷生物碱合成中的有趣应用

  摘要：

  2-羰基乙氧基苯甲酰氯与3,4-二氢-6,7-二甲氧基异喹啉的反应制得开环醛邻苯二甲酰亚胺（3），形成硫代乙缩醛并进行光环化，然后脱缩酮化，得到8,14-重氮基-13-羟基戊二烷（8）。

  DOI：

  10.1016/s0040-4039(00)96720-0

文献信息

• A Photochemical Approach to the Fully Functionalized Ring System of Chilinene, a Key Alkaloid of the Berberine Family
  作者：Paul H. Mazzocchi、Cliff R. King、Herman L. Ammon

  DOI：10.1016/s0040-4039(00)95444-3

  日期：1987.1

  The fully functionalized ring system of the berberine alkaloid chilinene has been prepared in a seven step synthesis. Key steps in the synthesis are the photocyclization of an imide-thioether and the oxidative formation with Pb(OAc)4 of a novel hexacyclic orthoester which led directly to the desired product.

  小ber碱生物碱基里恩的全功能环系统已通过七步合成法制备。合成中的关键步骤是酰亚胺-硫醚的光环化和新型六环原酸酯的Pb（OAc）4的氧化形成，直接导致所需的产物。
• Kessar, S V; Singh, Tejvir; Vohra, Rahul, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 11, p. 999 - 1005
  作者：Kessar, S V、Singh, Tejvir、Vohra, Rahul

  DOI：——

  日期：——
• A concise synthesis of the aporhoeadane skeleton
  作者：Bridget E. Piko、Amy L. Keegan、Michael S. Leonard

  DOI：10.1016/j.tetlet.2011.02.068

  日期：2011.4

  A concise synthesis of the isoindolobenzazepine aporhoeadane core is achieved in four steps from homoveratrylamine and ninhydrin. (C) 2011 Elsevier Ltd. All rights reserved.
• Dioxirane Epoxidation of 10-Membered-Ring Stilbene Lactams as Synthetic Precursors to Protoberberines
  作者：Gema Rodríguez、Luis Castedo、Domingo Domínguez、Carlos Saá、Waldemar Adam、Chantu R. Saha-Möller

  DOI：10.1021/jo981829n

  日期：1999.2.1

  Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid-catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13-hydroxytetrahydroprotoberberines and 13a-hydroxy-13-ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.
• KESSAR, S. V.;SINGH, TEJVIR;VOHRA, RAHUL, TETRAHEDRON LETT., 28,(1987) N 44, 5323-5326
  作者：KESSAR, S. V.、SINGH, TEJVIR、VOHRA, RAHUL

  DOI：——

  日期：——