5,7-dimethyl-5H,7H-dibenzo[b,d]azepin-6-one | 1065508-97-5

• 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: 5,7-dimethyl-5H,7H-dibenzo[b,d]azepin-6-one
• 英文别名: 5,7-dimethyl-7H-benzo[d][1]benzazepin-6-one
• CAS: 1065508-97-5
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: OJSADKGWQPQNHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  碘甲烷 、 5,7-二氢-5-甲基-6H-二苯并[b,d]氮杂卓-6-酮 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.17h， 以98%的产率得到5,7-dimethyl-5H,7H-dibenzo[b,d]azepin-6-one
  参考文献：
  名称：

  Atropisomeric Properties of the Dibenzo[b,d]azepin-6-one Nucleus

  摘要：

  Dibenzo[b,d]azepin-6-ones (2a,b) were separated by chiral HPLC into the aR- and aS-atropisomers with high stereochemical stability, and methylation at C7 of 2a stereoselectively gave the (aR*,7R*) isomer (4a), which converted to the thermodynamically stable (aS*,7R*) atropisomer (5a) after heating.

  DOI：

  10.1021/ol801968b

文献信息

• Synthesis of Dibenzazepinones by Palladium-Catalyzed Intramolecular Arylation of <i>o</i>-(2′-Bromophenyl)anilide Enolates
  作者：Xiaohong Pan、Craig S. Wilcox

  DOI：10.1021/jo101137r

  日期：2010.10.1

  A new approach for the convenient synthesis of dibenzazepinones is reported. The key step is the formation of the seven-membered ring through palladium-catalyzed intramolecular arylation of an anilide enolate. The reactions were completed in 10 min at 100 °C with moderate to excellent yields. Aminodibenzazepinone 1, the core structure in the γ-secretase inhibitor LY411575, can be prepared in five steps

  报道了一种方便合成二苯并ze庚酮的新方法。关键步骤是通过钯催化苯胺酸烯醇酯的分子内芳基化反应形成七元环。反应在100分钟内于10分钟内完成，产率中等至极好。γ-分泌酶抑制剂LY411575的核心结构氨基二苯并ze庚酮1可以由5个步骤由2-溴苯基硼酸和2-碘苯胺制备，总产率为60％。此处报道的合成方法与目前有趣的环系统的现有方法相比具有优势。
• [EN] MALONAMIDE DERIVATIVES BLOCKING THE ACTIVITY OF GAMA-SECRETASE<br/>[FR] DERIVES DE MALONAMIDE BLOQUANT L'ACTIVITE GAMA-SECRETASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005023772A1

  公开（公告）日：2005-03-17

  The invention relates to malonamide derivatives of formula (I), wherein: R1 is one of the following groups (Formulae a), b), c), d)); R2 is lower alkyl, lower alkinyl, -(CH2)n-O-lower alkyl, -(CH2)n-S-lower alkyl, -(CH2)n-CN, -(CR'R')n-CF3, -(CR'R')n-CHF2, -(CR'R')n-CH2F, -(CH2)n-C(O)O-lower alkyl, -(CH2)n-halogen, or is -(CH2)n-cycloalkyl, optionally substituted by one or more substituents, selected from the group consisting of phenyl, halogen or CF3; R',R' are independently from n and from each other hydrogen, lower alkyl, lower alkoxy, halogen or hydroxy; R3, R4 are independently from each other hydrogen, lower alkyl, lower alkoxy, phenyl or halogen; R5 is hydrogen, lower alkyl, -(CH2)n-CF3 or -(CH2)n-cycloalkyl; R6 is hydrogen or halogen; R7 is hydrogen or lower alkyl; R8 is hydrogen, lower alkyl, lower alkinyl, -(CH2)n-CF3,-(CH2)n-cycloalkyl or -(CH2)n-phenyl, optionally substituted by halogen; R9 is hydrogen, lower alkyl, -C(O)H, -C(O)-lower alkyl, -C(O)-CF3,-C(O)-CH2F,-C(O)-CHF2,-C(O)-cycloalkyl,-C(O)-(CH2)n-O-lower alkyl,-C(O)O-(CH2)n-cycloalkyl, -C(O)-phenyl, optionally substituted by one or more substituents selected from the group consisting of halogen or -C(O)O-lower alkyl, or is -S(O)2-lower alkyl, -S(O)2-CF3,-(CH2)n-cycloalkyl or is -(CH2)n-phenyl, optionally substituted by halogen; n is 0, 1, 2, 3 or 4; and to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixture thereof. These compounds may be used for the treatment of Alzheimer's disease.

  本发明涉及式（I）的马隆酰胺衍生物，其中：R1是以下组之一（式a，b，c，d）之一；R2是较低的烷基，较低的烯烃基，-(CH2)n-O-较低的烷基，-(CH2)n-S-较低的烷基，-(CH2)n-CN，-(CR'R')n-CF3，-(CR'R')n-CHF2，-(CR'R')n-CH2F，-(CH2)n-C（O）O-较低的烷基，-(CH2)n-卤素，或者是-(CH2)n-环烷基，选自苯基，卤素或CF3的一种或多种取代基；R'，R'分别独立于n和彼此，是氢，较低的烷基，较低的烷氧基，卤素或羟基；R3，R4独立于彼此，是氢，较低的烷基，较低的烷氧基，苯基或卤素；R5是氢，较低的烷基，-(CH2)n-CF3或-(CH2)n-环烷基；R6是氢或卤素；R7是氢或较低的烷基；R8是氢，较低的烷基，较低的烯烃基，-(CH2)n-CF3，-(CH2)n-环烷基或-(CH2)n-苯基，选自卤素的一种或多种取代基；R9是氢，较低的烷基，-C（O）H，-C（O）-较低的烷基，-C（O）-CF3，-C（O）-CH2F，-C（O）-CHF2，-C（O）-环烷基，-C（O）-(CH2)n-O-较低的烷基，-C（O）O-(CH2)n-环烷基，-C（O）-苯基，选自卤素或-C（O）O-较低的烷基的一种或多种取代基，或者是-S（O）2-较低的烷基，-S（O）2-CF3，-(CH2)n-环烷基或是-(CH2)n-苯基，选自卤素的一种或多种取代基；n为0，1，2，3或4；以及药学上适用的酸盐，光学纯对映体，混合物或二对映异构体的制备方法。这些化合物可用于治疗阿尔茨海默病。
• CYCLIC MALONAMIDES AS INHIBITORS OF ABETA PROTEIN PRODUCTION
  申请人：Olson Richard E.

  公开号：US20100009965A1

  公开（公告）日：2010-01-14

  This invention relates to novel cyclic malonamides having the formula (I): to their pharmaceutical compositions and to their methods of use. These novel compounds inhibit the processing of amyloid precursor protein and, more specifically, inhibit the production of Aβ-peptide, thereby acting to prevent the formation of neurological deposits of amyloid protein. More particularly, the present invention relates to the treatment of neurological disorders related to β-amyloid production such as Alzheimer's disease and Down's Syndrome.

  本发明涉及具有公式（I）的新型环状马隆酰胺，其药物组成物和使用方法。这些新化合物抑制淀粉样前体蛋白的加工，更具体地抑制Aβ-肽的产生，从而防止神经沉积物的淀粉样蛋白形成。更具体地，本发明涉及治疗与β-淀粉样蛋白产生相关的神经疾病，如阿尔茨海默病和唐氏综合症。
• CYCLIC MALONAMIDES AS INHIBITORS OF Abeta PROTEIN PRODUCTION
  申请人：Olson Richard E.

  公开号：US20090264419A1

  公开（公告）日：2009-10-22

  This invention relates to novel cyclic malonamides having the formula (I): to their pharmaceutical compositions and to their methods of use. These novel compounds inhibit the processing of amyloid precursor protein and, more specifically, inhibit the production of Aβ-peptide, thereby acting to prevent the formation of neurological deposits of amyloid protein. More particularly, the present invention relates to the treatment of neurological disorders related to β-amyloid production such as Alzheimer's disease and Down's Syndrome.

  本发明涉及具有以下公式（I）的新型环状马隆酰胺、其制药组合物以及使用方法。这些新化合物抑制淀粉样前体蛋白的加工，更具体地抑制Aβ-肽的产生，从而防止神经沉积物的淀粉样蛋白形成。更具体地，本发明涉及与β-淀粉样蛋白产生有关的神经系统疾病的治疗，例如阿尔茨海默病和唐氏综合症。
• Hydroxyalkanoylaminolactams and related structures as inhibitors of Alphabeta protein production
  申请人：Olson E. Richard

  公开号：US20070027132A1

  公开（公告）日：2007-02-01

  This invention relates to novel lactams having the formula (I): to their pharmaceutical compositions and to their methods of use. These novel compounds inhibit the processing of amyloid precursor protein and, more specifically, inhibit the production of Aβ-peptide, thereby acting to prevent the formation of neurological deposits of amyloid protein. More particularly, the present invention relates to the treatment of neurological disorders related to β-amyloid production such as Alzheimer's disease and Down's Syndrome.

  本发明涉及具有公式（I）的新型内酰胺，其制药组合物以及使用方法。这些新型化合物抑制淀粉样前体蛋白的加工，更具体地抑制Aβ-肽的产生，从而防止神经沉积物的淀粉样蛋白形成。更具体地，本发明涉及与β-淀粉样蛋白产生相关的神经系统疾病的治疗，例如阿尔茨海默病和唐氏综合症。