1-(p-Tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine | 20426-63-5

• 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: 1-(p-Tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine；1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine；1-(p-toluenesulfonyl)-2,3,4,5-tetrahydrobenzazepine；2,3,4,5-Tetrahydro-1-tosyl<1>benzazepin；N-p-Toluolsulfonyl-2.3.4.5-tetrahydro-1-benzazepin；1-Tosyl-2,3,4,5-tetrahydro-1H-1-benzoazepine；1-(4-methylphenyl)sulfonyl-2,3,4,5-tetrahydro-1-benzazepine
• CAS: 20426-63-5
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: VDKPYIVOTCSPGI-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88.5 °C
• 沸点：
  454.6±48.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(p-Tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 在 盐酸 、 三氯化铝 、 三乙胺 作用下， 反应 24.0h， 生成 8-Acetyl-1-methylcarbamoyl-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Ishihara, Yuji; Tanaka, Toshimasa; Goto, Giichi, Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3401 - 3406

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[2-(4-Hydroxy-butyl)-phenyl]-4-methyl-benzenesulfonamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-(p-Tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  S（N）2反应中离去基团的催化活化。

  摘要：

  作为我们的三氟甲磺酸汞催化反应的扩展，实现了S（N）2反应中离去基团的新型催化活化。4-戊戊酸苯胺基乙酯的衍生物与催化量的Hg（OTf）（2）平稳反应，可在非常温和的条件下以优异的收率得到高效的二氢吲哚衍生物。光学纯仲醇衍生物的反应导致立体化学的转化，这是S（N）2反应的确定特征。该程序适用于苯并ze庚因的合成。

  DOI：

  10.1021/ol701737x

文献信息

• Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives
  作者：Shital Chattopadhyay、Debalina Ghosh、Latibuddin Thander、Sanjay Ghosh

  DOI：10.1055/s-0028-1087298

  日期：2008.12

  A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance.

  基于 aza-Claisen 重排和闭环复分解反应的顺序应用作为关键步骤的合成策略已被开发用于合成各种与药物相关的 1-苯并氮杂衍生物。
• Central Cholinergic Agents. 6. Synthesis and Evaluation of 3-[1-(Phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)- 1-propanones and Their Analogs as Central Selective Acetylcholinesterase Inhibitors
  作者：Yuji Ishihara、Keisuke Hirai、Masaomi Miyamoto、Giichi Goto

  DOI：10.1021/jm00041a007

  日期：1994.7

  In an attempt to find central selective acetylcholinesterase (AChE) inhibitors, 3-[1-(phenyl-methyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanones 9 and their analogs were designed on the basis of our working hypothesis of the enzyme's active site. These compounds were prepared by regioselective Friedel-Crafts acylation of 2,3,4,5-tetrahydro-1H-benzazepines and related nitrogen heterocycles as a key step. Most compounds showed potent inhibitory activities with IC(50)s in the 10-300 nM range. In order to estimate their central selectivities, we examined their effects on the apomorphine-induced circling behavior in rats with unilateral striatal lesions. Among compounds with potent AChE inhibition, 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone fumarate (9a, TAK-147) (IC50 of AChE inhibition = 97.7 nM) inhibited the circling behavior at 3 mg/kg po, in which it had no significant effect on peripheral cholinergic effects. This demonstrates that 9a has favorable central selectivity. Furthermore, 9a significantly ameliorated diazepam-induced passive avoidance deficit at 1 mg/kg po. The benzazepine derivative 9a was selected as a candidate for clinical evaluation.
• EP1475368
  申请人：——

  公开号：——

  公开（公告）日：——
• Ishihara, Yuji; Tanaka, Toshimasa; Goto, Giichi, Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3401 - 3406
  作者：Ishihara, Yuji、Tanaka, Toshimasa、Goto, Giichi

  DOI：——

  日期：——
• Catalytic Activation of the Leaving Group in the S_N2 Reaction
  作者：Hirofumi Yamamoto、Ghanshyam Pandey、Yumiko Asai、Mayo Nakano、Atsushi Kinoshita、Kosuke Namba、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1021/ol701737x

  日期：2007.9.1

  catalytic activation of the leaving group in the S(N)2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)(2) to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives

  作为我们的三氟甲磺酸汞催化反应的扩展，实现了S（N）2反应中离去基团的新型催化活化。4-戊戊酸苯胺基乙酯的衍生物与催化量的Hg（OTf）（2）平稳反应，可在非常温和的条件下以优异的收率得到高效的二氢吲哚衍生物。光学纯仲醇衍生物的反应导致立体化学的转化，这是S（N）2反应的确定特征。该程序适用于苯并ze庚因的合成。