5-methyl-1,3,4,5-tetrahydro-1-benzazepin-2-one | 104479-28-9

• 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: 5-methyl-1,3,4,5-tetrahydro-1-benzazepin-2-one
• 英文别名: 5-methyl-1,3,4,5-tetrahydro-benz[b]azepin-2-one；5-Methyl-1,3,4,5-tetrahydro-benz[b]azepin-2-on；2,3,4,5-tetrahydro-5-methyl-1H-1-benzazepin-2-one；5-Methyl-4,5-dihydro-1h-1-benzazepin-2(3h)-one
• CAS: 104479-28-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: QKPXZBCOUCASTL-UHFFFAOYSA-N

物化性质

• 沸点：
  315.5±21.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-1,3,4,5-tetrahydro-1-benzazepin-2-one 在 硫酸 、 氢气 、 硝酸 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 7-(N',N''-bismethoxycarbonylguanidino)-5-methyl-1,3,4,5-tetrahydro-1-benzazepin-2-one
  参考文献：
  名称：

  Rajappa, Srinivasachari; Sreenivasan, Ramaswami; Khalwadekar, Asha, Journal of Chemical Research, Miniprint, 1986, # 5, p. 1657 - 1675

  摘要：

  DOI：
• 作为产物：
  描述：

  5-methyl-1,3-dihydro-2H-1-benzazepin-2-one 在 溶剂黄146 、 铂 作用下， 生成 5-methyl-1,3,4,5-tetrahydro-1-benzazepin-2-one
  参考文献：
  名称：

  Bertho, Chemische Berichte, 1957, vol. 90, p. 29,39

  摘要：

  DOI：

文献信息

• Regioselective Palladium(II)-Catalyzed Synthesis of Five- or Seven-Membered Ring Lactones and Five-, Six- or Seven-Membered Ring Lactams by Cyclocarbonylation Methodology
  作者：Bassam El Ali、Kazumi Okuro、Giuseppe Vasapollo、Howard Alper

  DOI：10.1021/ja953403l

  日期：1996.1.1

  affording five- or seven-membered ring lactones (bicyclic, tricyclic, and pentacyclic) as the principal products, often in excellent yields. Use of 2-aminostyrenes as reactants and catalytic quantities of palladium acetate and tricyclohexylphosphine, affords five-membered ring lactams in high yield and selectivity. Bicyclic and tricyclic heterocycles containing six-membered ring lactams can be synthesized

  2-烯丙基苯酚在催化量的阳离子钯 (II) 络合物 [(PCy3)2Pd(H)(H2O)]+BF4- 或乙酸钯和 1,4-双(二苯基膦) 存在下与一氧化碳和氢气反应丁烷，提供五元或七元环内酯（双环、三环和五环）作为主要产物，通常收率极好。使用 2-氨基苯乙烯作为反应物和催化量的乙酸钯和三环己基膦，以高产率和选择性提供五元环内酰胺。使用催化体系 Pd(OAc)2/PPh3，2-烯丙胺与 CO/H2 反应可以合成含有六元环内酰胺的双环和三环杂环，同时使用 1, 4-双（二苯基膦基）丁烷在后一过程中代替 PPh3 导致以良好的产率形成七元内酰胺苯并氮杂酮。区域化学控制取决于钯催化剂的性质、气体的相对压力和溶剂。
• An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P®)
  作者：John Kallikat Augustine、Rajesha Kumar、Agnes Bombrun、Ashis Baran Mandal

  DOI：10.1016/j.tetlet.2010.12.090

  日期：2011.3

  An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P®) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include

  描述了一种由催化量（15摩尔％）的丙基膦酸酐介导的将酮肟的贝克曼重排成酰胺的有效方法。Aldoximes在室温下与T3P（15 mol％）反应后，进行了二阶Beckmann重排，从而以优异的产率提供了相应的腈。这种环境友好协议的主要优点包括程序简单，尤其是产品隔离容易。
• Triazabenzo[E]Azulene Derivatives for the Treatment Of Tumors
  申请人：Hoelzemann Guenter

  公开号：US20100063028A1

  公开（公告）日：2010-03-11

  Novel triazabenzo[e]azulene derivatives of the formula, (I) in which R 1 , R 2 and R 3 have the meanings indicated in Claim 1, are inhibitors of TGF-beta receptor kinase and can be employed, inter alia, for the treatment of tumours.

  式(I)中，R1、R2和R3具有权利要求1所示的含义，是TGF-beta受体激酶的抑制剂，可用于治疗肿瘤等方面。
• N-biphenyl-3-amido substituted benzolactams stimulate growth hormone
  申请人：Merck & Co., Inc.

  公开号：US05317017A1

  公开（公告）日：1994-05-31

  There are disclosed certain compounds identified as N-biphenyl-3-amido substituted benzolactams which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. Growth promoting compositions containing such benzolactams as the active ingredient thereof are also disclosed.

  本发明公开了某些化合物，这些化合物被鉴定为N-联苯基-3-酰胺取代苯并内酰胺，可促进人类和动物的生长激素释放。该特性可用于促进食用动物的生长，使可食用肉制品的生产更加高效，并且在人类中，可增加那些患有正常分泌天然生长激素缺乏的人的身高。本发明还公开了包含该苯并内酰胺作为其活性成分的生长促进组合物。
• Discovery of novel triazolobenzazepinones as γ-secretase modulators with central Aβ42 lowering in rodents and rhesus monkeys
  作者：Christian Fischer、Susan L. Zultanski、Hua Zhou、Joey L. Methot、Sanjiv Shah、Ikuo Hayashi、Bethany L. Hughes、Christopher M. Moxham、Nathan W. Bays、Nadya Smotrov、Armetta D. Hill、Bo-Sheng Pan、Zhenhua Wu、Lily Y. Moy、Flobert Tanga、Candia Kenific、Jonathan C. Cruz、Deborah Walker、Melanie Bouthillette、George N. Nikov、Sujal V. Deshmukh、Valentina V. Jeliazkova-Mecheva、Damaris Diaz、Maria S. Michener、Jacquelynn J. Cook、Benito Munoz、Mark S. Shearman

  DOI：10.1016/j.bmcl.2015.07.003

  日期：2015.9

  Synthesis and SAR studies of novel triazolobenzazepinones as gamma secretase modulators (GSMs) are presented in this communication. Starting from our azepinone leads, optimization studies toward improving central lowering of A beta 42 led to the discovery of novel benzo-fused azepinones. Several benzazepinones were profiled in vivo and found to lower brain A beta 42 levels in Sprague Dawley rats and transgenic APP-YAC mice in a dose-dependent manner after a single oral dose. Compound 34 was further progressed into a pilot study in our cisterna-magna-ported rhesus monkey model, where we observed robust lowering of CSF A beta 42 levels. (C) 2015 Elsevier Ltd. All rights reserved.