(2R,11aS)-7-methyl-2-hydroxy-1,2,3,10,11,11a-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione | 243981-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (2R,11aS)-7-methyl-2-hydroxy-1,2,3,10,11,11a-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
• 英文别名: (6aS,8R)-8-hydroxy-2-methyl-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione
• CAS: 243981-19-3
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: IHDDVNKTIFTWMH-KCJUWKMLSA-N

物化性质

• 沸点：
  557.0±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,11aS)-7-methyl-2-hydroxy-1,2,3,10,11,11a-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione 在 吡啶 、 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.83h， 生成 7-methyl-9-oxo-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline-1-carboxylic acid
  参考文献：
  名称：

  Jolivet-Fouchet, Sandrine; Fabis, Frederic; Bovy, Philippe, Heterocycles, 1999, vol. 51, # 6, p. 1257 - 1273

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(2R,11aS)-7-methyl-2-hydroxy-1,2,3,10,11,11a-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
  参考文献：
  名称：

  Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81

  摘要：

  An efficient method for the reduction of aromatic azides in both solution and solid-phase has been developed by employing (BF3OEt2)-O-./EtSH. This report also describes resin cleavage employing this reagent system. Further, this protocol has been utilized for the solution as well as the solid-phase synthesis of pyrrolo[2, 1-c][1,4]benzodiazepines, including the naturally occurring antibiotic DC-81 and fused [2,1-b]quinazolinones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.025

文献信息

• An Efficient Selective Reduction of Aromatic Azides to Amines Employing BF₃·OEt₂/NaI: Synthesis of Pyrrolobenzodiazepines
  作者：Ahmed Kamal、Ch. Reddy、N. Shankaraiah、N. Markandeya

  DOI：10.1055/s-2008-1072742

  日期：2008.5

  A selective and facile method for the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through intramolecular reductive-cyclization process. In this protocol the reagent systems are amenable for the generation

  使用三氟化硼乙醚合物和碘化钠将芳族叠氮化物还原为胺的选择性和简便方法。该方法已应用于通过分子内还原环化过程制备具有生物学意义的含亚胺的吡咯并苯二氮卓类及其双内酰胺。在该协议中，试剂系统适用于生成溶液相组合合成。
• An expedient route to aromatic pyrrolo[2,1-c][1,4]benzodiazepines and a study of their reactivity
  作者：Frédéric Fabis、Jana Sopkova-de Oliveira Santos、Sandrine Fouchet-Jolivet、Sylvain Rault

  DOI：10.1016/s0040-4039(01)00957-1

  日期：2001.7

  2-Hydroxypyrrolo[2,1-c][1,4]benzodiazepines were aromatised in refluxing thionyl chloride into 11-chloropyrrolo[2,1-c][1,4]benzodiazepines in high yield. This aromatic system is doubly reactive towards nucleophiles leading to rearranged products such as iminobenzoxazines and quinazolines.

  2-羟基吡咯并[2,1- c ^ ] [1,4]苯并二氮杂类中在回流的亚硫酰氯为11个氯吡咯芳香烃[2,1- c ^ ] [1,4]高收率苯二氮。该芳族体系对亲核试剂具有双反应性，从而导致重排产物，如亚氨基苯并恶嗪和喹唑啉。
• Microwave Assisted Synthesis of Pyrrolo[2,1-<i>c</i>][1,4]benzodiazepine-5,11-diones
  作者：Ahmed Kamal、B. S. Narayan Reddy、G. Suresh Kumar Reddy

  DOI：10.1055/s-1999-2812

  日期：1999.8
• Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81
  作者：Ahmed Kamal、N. Shankaraiah、K. Laxma Reddy、V. Devaiah

  DOI：10.1016/j.tetlet.2006.04.025

  日期：2006.6

  An efficient method for the reduction of aromatic azides in both solution and solid-phase has been developed by employing (BF3OEt2)-O-./EtSH. This report also describes resin cleavage employing this reagent system. Further, this protocol has been utilized for the solution as well as the solid-phase synthesis of pyrrolo[2, 1-c][1,4]benzodiazepines, including the naturally occurring antibiotic DC-81 and fused [2,1-b]quinazolinones. (c) 2006 Elsevier Ltd. All rights reserved.
• Jolivet-Fouchet, Sandrine; Fabis, Frederic; Bovy, Philippe, Heterocycles, 1999, vol. 51, # 6, p. 1257 - 1273
  作者：Jolivet-Fouchet, Sandrine、Fabis, Frederic、Bovy, Philippe、Ochsenbein, Philippe、Rault, Sylvain

  DOI：——

  日期：——