(Z)-11-(2-oxopropylidene)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(10H)-one | 1206881-19-7

• 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: (Z)-11-(2-oxopropylidene)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(10H)-one
• 英文别名: (+/-)-fuligocandin A；11-(2-Oxopropylidene)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one；(6Z)-6-(2-oxopropylidene)-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
• CAS: 1206881-19-7
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: QIABJYAEDCYFEV-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2,4,10,11,11a-hexahydro-11-thioxo-3H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 在 三乙烯二胺 、 sodium hydride 、 三甲氧基磷 作用下， 以 二甲基亚砜 为溶剂， 反应 1.17h， 生成 (Z)-11-(2-oxopropylidene)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(10H)-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

• Erratum
  作者：More, Satish S.、Shanmughapriya、Lingam、Patel

  DOI：10.1080/00397910903084904

  日期：2009.6.23
• 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.

表征谱图