6-chloro-1-tosyl-1H-benzo[b]azepin-3(2H)-one | 1439383-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-chloro-1-tosyl-1H-benzo[b]azepin-3(2H)-one
• 英文别名: 6-chloro-1-(4-methylphenyl)sulfonyl-2H-1-benzazepin-3-one
• CAS: 1439383-98-8
• 化学式: C₁₇H₁₄ClNO₃S
• 分子量: 347.822
• InChiKey: MBSNTCYOFMDWFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-chloro-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 6-chloro-1-tosyl-1H-benzo[b]azepin-3(2H)-one
  参考文献：
  名称：

  Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis–Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes

  摘要：

  A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement and Bronsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (2)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones efficiently is reported. The reactions proceed rapidly under mild and operationally straightforward conditions for a wide variety of aldehyde substrates containing electron-withdrawing, electron-donating, and sterically demanding functional groups and afforded the corresponding benzo-fused azaheterocyclic products in moderate to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.069

文献信息

• Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis–Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes
  作者：Ella Min Ling Sze、Ming Joo Koh、Yen Min Tjia、Weidong Rao、Philip Wai Hong Chan

  DOI：10.1016/j.tet.2013.04.069

  日期：2013.7

  A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement and Bronsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (2)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones efficiently is reported. The reactions proceed rapidly under mild and operationally straightforward conditions for a wide variety of aldehyde substrates containing electron-withdrawing, electron-donating, and sterically demanding functional groups and afforded the corresponding benzo-fused azaheterocyclic products in moderate to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.