1-(2-acetyl-2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-3-(1-methoxycarbonylpiperidine-4-yl)propan-1-one | 160300-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-(2-acetyl-2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-3-(1-methoxycarbonylpiperidine-4-yl)propan-1-one
• 英文别名: Methyl 4-[3-(2-acetyl-1,3,4,5-tetrahydro-2-benzazepin-8-yl)-3-oxopropyl]piperidine-1-carboxylate
• CAS: 160300-42-5
• 化学式: C₂₂H₃₀N₂O₄
• 分子量: 386.491
• InChiKey: NRPDJQYJWNISSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-acetyl-2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-3-(1-methoxycarbonylpiperidine-4-yl)propan-1-one 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以70%的产率得到1-(2-acetyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)-3-piperidin-4-yl-propan-1-one
  参考文献：
  名称：

  Regioselective Friedel–Crafts acylation of 2,3,4,5-tetrahydro-1H-2-benzazepine and related nitrogen heterocycles

  摘要：

  It is revealed that NH-protected 2,3,4,5-tetrahydro-1H-2-benzazepine 4 is acylated on C-8 with greater than 95% regioselectivity. This regioselectivity has been applied to the synthesis of 3-(1-benzylpiperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)propan-1-one 3a, an inhibitor of acetylcholinesterase (AChE). The regioselectivities of the acylation of the following nitrogen heterocycles have also been studied: 4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepine 6, 2,3,4,5-tetrahydro-1H-2-benzazepin-3-one 7, 2,3,4,5-tetrahydro-1H-3-benzazepin-2-one 8, 7,11b,12,13-tetrahydro-5H-isoindolo[2,1-b][2] benzazepin-7-one 9 and 6,7,9,13b-tetrahydro-5H-isoindolo[1,2-a][2]benzazepin-9-one 10. A molecular orbital (MO) calculation on the Lewis acid coordinated substrates has been used for predicting regioselectivity.

  DOI：

  10.1039/p19940002993
• 作为产物：
  描述：

  3-[1-(acetyl)-4-piperidinyl]propionic acid 在 盐酸 、 sodium hydroxide 、 三氯化铝 、 氯化亚砜 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 27.5h， 生成 1-(2-acetyl-2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-3-(1-methoxycarbonylpiperidine-4-yl)propan-1-one
  参考文献：
  名称：

  Regioselective Friedel–Crafts acylation of 2,3,4,5-tetrahydro-1H-2-benzazepine and related nitrogen heterocycles

  摘要：

  It is revealed that NH-protected 2,3,4,5-tetrahydro-1H-2-benzazepine 4 is acylated on C-8 with greater than 95% regioselectivity. This regioselectivity has been applied to the synthesis of 3-(1-benzylpiperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)propan-1-one 3a, an inhibitor of acetylcholinesterase (AChE). The regioselectivities of the acylation of the following nitrogen heterocycles have also been studied: 4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepine 6, 2,3,4,5-tetrahydro-1H-2-benzazepin-3-one 7, 2,3,4,5-tetrahydro-1H-3-benzazepin-2-one 8, 7,11b,12,13-tetrahydro-5H-isoindolo[2,1-b][2] benzazepin-7-one 9 and 6,7,9,13b-tetrahydro-5H-isoindolo[1,2-a][2]benzazepin-9-one 10. A molecular orbital (MO) calculation on the Lewis acid coordinated substrates has been used for predicting regioselectivity.

  DOI：

  10.1039/p19940002993

文献信息

• Regioselective Friedel–Crafts acylation of 2,3,4,5-tetrahydro-1H-2-benzazepine and related nitrogen heterocycles
  作者：Yuji Ishihara、Toshimasa Tanaka、Seiji Miwatashi、Akira Fujishima、Giichi Goto

  DOI：10.1039/p19940002993

  日期：——

  It is revealed that NH-protected 2,3,4,5-tetrahydro-1H-2-benzazepine 4 is acylated on C-8 with greater than 95% regioselectivity. This regioselectivity has been applied to the synthesis of 3-(1-benzylpiperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)propan-1-one 3a, an inhibitor of acetylcholinesterase (AChE). The regioselectivities of the acylation of the following nitrogen heterocycles have also been studied: 4-formyl-2,3,4,5-tetrahydro-1,4-benzoxazepine 6, 2,3,4,5-tetrahydro-1H-2-benzazepin-3-one 7, 2,3,4,5-tetrahydro-1H-3-benzazepin-2-one 8, 7,11b,12,13-tetrahydro-5H-isoindolo[2,1-b][2] benzazepin-7-one 9 and 6,7,9,13b-tetrahydro-5H-isoindolo[1,2-a][2]benzazepin-9-one 10. A molecular orbital (MO) calculation on the Lewis acid coordinated substrates has been used for predicting regioselectivity.