(6Z,6aS)-6-[(E)-4-[1-(4-nitrophenyl)sulfonylindol-3-yl]-2-oxobut-3-enylidene]-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one | 1271450-10-2

• 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: (6Z,6aS)-6-[(E)-4-[1-(4-nitrophenyl)sulfonylindol-3-yl]-2-oxobut-3-enylidene]-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
• CAS: 1271450-10-2
• 化学式: C₃₀H₂₄N₄O₆S
• 分子量: 568.61
• InChiKey: CXCHSGYAWCVRKT-VYMNMVJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6Z,6aS)-6-[(E)-4-[1-(4-nitrophenyl)sulfonylindol-3-yl]-2-oxobut-3-enylidene]-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one 在 sodium hydride 、 苯硫酚 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.03h， 以0.25 g的产率得到fuligocandin B
  参考文献：
  名称：

  One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

  摘要：

  Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DAIS proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.

  DOI：

  10.1021/jo101864n
• 作为产物：
  描述：

  (S,E)-11-((4-(1-((4-nitrophenyl)sulfonyl)-1H-indol-3-yl)-2-oxobut-3-en-1-yl)thio)-1,2,3,11a-tetrahydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 以 二甲基亚砜 为溶剂， 反应 2.0h， 以0.323 g的产率得到(6Z,6aS)-6-[(E)-4-[1-(4-nitrophenyl)sulfonylindol-3-yl]-2-oxobut-3-enylidene]-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
  参考文献：
  名称：

  One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

  摘要：

  Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DAIS proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.

  DOI：

  10.1021/jo101864n

文献信息

• One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides
  作者：Birgitta Pettersson、Vedran Hasimbegovic、Jan Bergman

  DOI：10.1021/jo101864n

  日期：2011.3.18

  Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DAIS proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.