(R)-6-Methylazepan-2-one | 1123-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (R)-6-Methylazepan-2-one
• 英文别名: (6R)-6-methylazepan-2-one
• CAS: 1123-06-4
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: XDAWFENPCDYKEA-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (R)-6-Methylazepan-2-one 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Concise Formation of Spirocyclic Compounds for Marine Phycotoxins

  摘要：

  The stereoselective construction of azaspiro[5.6]dodecenone skeletons by the chiral BOX/copper-mediated Diels-Alder reaction is described. The cycloaddition reaction of alpha-methylene caprolactams and functionalized dienes allows the concise formation of spirocyclic structures of marine phycotoxins, such as pinnatoxin and spirolide.

  DOI：

  10.3987/com-16-s(s)34
• 作为产物：
  描述：

  6-(叔丁基二甲基硅氧基)己酸 在 4-二甲氨基吡啶 、 sodium hypochlorite 、 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 sodium azide 、 2,2,6,6-四甲基哌啶氧化物 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 三甲基乙酰氯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (R)-6-Methylazepan-2-one
  参考文献：
  名称：

  Concise Formation of Spirocyclic Compounds for Marine Phycotoxins

  摘要：

  The stereoselective construction of azaspiro[5.6]dodecenone skeletons by the chiral BOX/copper-mediated Diels-Alder reaction is described. The cycloaddition reaction of alpha-methylene caprolactams and functionalized dienes allows the concise formation of spirocyclic structures of marine phycotoxins, such as pinnatoxin and spirolide.

  DOI：

  10.3987/com-16-s(s)34

文献信息

• PYRAZOLE COMPOUND AND PHARMACEUTICAL USE THEREOF
  申请人：MIURA Tomoya

  公开号：US20130085132A1

  公开（公告）日：2013-04-04

  The present invention provides a pyrazole compound of the following general Formula [Ib] having SGLT1 inhibitory activity, or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the same, and its pharmaceutical use: wherein each symbol is the same as defined in the description.

  本发明提供了一种具有SGLT1抑制活性的下式[Ib]所示的吡唑化合物、或其药物可接受的盐、包含该化合物的药物组合物及其医药用途： 其中每个符号如说明书中所定义。
• Amidino derivatives useful as nitric oxide synthase inhibitors
  申请人：G.D. SEARLE & CO.

  公开号：EP0897912A1

  公开（公告）日：1999-02-24

  The current invention discloses useful pharmaceutical compositions containing amidino derivatives of formula (I) as nitric oxide synthase inhibitors.

  本发明公开了含有式（I）脒基衍生物作为一氧化氮合酶抑制剂的有用药物组合物。
• PYRAZOLE COMPOUND AND USE THEREOF FOR MEDICAL PURPOSES
  申请人：Japan Tobacco, Inc.

  公开号：EP2784074A1

  公开（公告）日：2014-10-01

  A compound of the following general Formula [Ib]: , wherein each symbol is the same as defined in the description; or a pharmaceutically acceptable salt thereof.

  以下通式[Ib]的化合物： 其中各符号与描述中定义的相同；或其药学上可接受的盐。
• Syntheses and rearrangements of spirocyclic oxaziridines derived from unsymmetrical ketones
  作者：Jeffrey Aube、Marlys Hammond、Elyse Gherardini、Fusao Takusagawa

  DOI：10.1021/jo00002a006

  日期：1991.1

  Oxaziridines provide useful alternatives to the Beckmann rearrangement and Schmidt reaction for ring enlargement of cyclic ketones. The procedure involves the condensation of the ketone in question with optically active alpha-methylbenzylamine, oxidation of the resultant imine, and photolysis to afford ring-expanded lactams. The alpha-phenylethyl substituent can be removed after photolysis to yield the N-unsubstituted lactam. When a distal ketone substituent is present, the oxaziridines can be synthesized stereoselectively. Thus, optically active ketones can be converted to either ring-expanded lactam by choice of either enantiomer of optically active alpha-methylbenzylamine. Ketones bearing adjacent substitution are generally not amenable to such regiocontrol because the resident substituent is the key stereocontrol element for the oxaziridine synthesis, although a notable exception is 2-methoxycyclohexanone. Stereogenic centers present in such compounds undergo epimerization during the couse of the reaction sequence; in addition, substrates containing substantial amounts of enamine give rise to novel doubly oxygenated products upon oxidation. Finally, the conformational behavior of the side chains in both oxaziridines and their product lactams permits some key stereochemical assignments to be made, on the basis of chemical shift trends in the NMR spectra of these materials.
• 2-Iminohomopiperidinium Salts as Selective Inhibitors of Inducible Nitric Oxide Synthase (iNOS)
  作者：Donald W. Hansen,、Karen B. Peterson、Mahima Trivedi、Steven W. Kramer、Ronald K. Webber、Foe S. Tjoeng、William M. Moore、Gina M. Jerome、Christine M. Kornmeier、Pamela T. Manning、Jane R. Connor、Thomas P. Misko、Mark G. Currie、Barnett S. Pitzele

  DOI：10.1021/jm9704715

  日期：1998.4.1

  An attractive approach to the treatment of inflammatory conditions such as osteo-and rheumatoid arthritis, inflammatory bowel disease, and sepsis is through the selective inhibition of human inducible nitric oxide synthase (hiNOS) since localized excess nitric oxide (NO) release has been implicated in the pathology of these diseases. A series of monosubstituted iminohomopiperidinium salts possessing lipophilic functionality at ring positions 3, 5, 6, and 7 has been synthesized, and series members have demonstrated the ability to inhibit the hiNOS isoform with an IC50 as low as 160 nM (7). Compounds were found that selectively inhibit hiNOS over the human endothelial constitutive enzyme (heNOS) with a heNOS/hiNOS IC50 ratio in excess of 100 and as high as 314 (9). Potencies for inhibition of hiNOS and the human neuronal constitutive enzyme (hnNOS) are comparable. Substitution in the 3 and 7 positions provides compounds that exhibit the greatest degree of selectivity for hiNOS and hnNOS over heNOS. Submicromolar potencies for 6 and 7 in a mouse RAW cell assay demonstrated the ability of these compounds to inhibit iNOS in a cellular environment. These latter compounds were also found to be orally bioavailable and efficacious due to their ability to inhibit the increase in plasma nitrite/nitrate levels in a rat LPS model.