(+/-)-fuligocandin B | 1206881-20-0

• 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: (+/-)-fuligocandin B
• 英文别名: (6Z)-6-[(E)-4-(1H-indol-3-yl)-2-oxobut-3-enylidene]-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
• CAS: 1206881-20-0
• 化学式: C₂₄H₂₁N₃O₂
• 分子量: 383.45
• InChiKey: NYQWWRQVZXCLIH-NBKBGXPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-chloro-4-(1-(4-nitrophenylsulfonyl)-1H-indol-3-yl)but-3-en-2-one 在 甲醇 、 sodium hydride 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 生成 (+/-)-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

文献信息

• Total synthesis of fuligocandines A and B
  作者：Birgitta Pettersson、Vedran Hasimbegovic、Jan Bergman

  DOI：10.1016/j.tetlet.2009.10.134

  日期：2010.1

  A practical synthesis of the biologically active cycloanthranilylproline derivatives fuligocandines A and B is described, starting from L-proline and isatoic anhydride, employing an Eschenmoser episulfide contraction as the key step. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.