(R)-hexahydro-4-methyl-2H-azepin-2-one | 1123-08-6

• 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)-hexahydro-4-methyl-2H-azepin-2-one
• 英文别名: hexahydro-4R-methyl-1H-azepin-2-one；4-Methyl-2-oxo-hexamethylen-imin；(4R)-4-methylazepan-2-one
• CAS: 1123-08-6
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: SUXWXEJDQZBDNL-ZCFIWIBFSA-N

物化性质

• 熔点：
  98-103 °C
• 沸点：
  269.3±9.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

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)-hexahydro-4-methyl-2H-azepin-2-one 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Structural Analysis of .beta.-Turn Mimics Containing a Substituted 6-Aminocaproic Acid Linker

  摘要：

  A series of beta-turn models have been prepared consisting of the dipeptide Ala-Gly cyclized with all stereoisomers of 6-amino-3,5-dimethylcaproic acid and 6-amino-3-methylcaproic acid, as were related peptides based on Gly-Gly and Ala-Ala, The requisite linkers were made using routes featuring stereoselective ring-expansion reactions and the syntheses completed using standard methodology. A preliminary examination of these compounds has been carried out using NMR spectroscopy, circular dichroism, and, in several cases, X-ray crystallography. These studies indicate that, depending on linker stereochemistry, different proportions of type II and type I turns were observed in solution. Both type I and type II turns were observed in the solid state.

  DOI：

  10.1021/ja00124a001
• 作为产物：
  描述：

  在 sodium hydride 作用下， 生成 (R)-hexahydro-4-methyl-2H-azepin-2-one
  参考文献：
  名称：

  1,7-Asymmetric Induction in a Nitrogen Ring Expansion Process Facilitated by in Situ Tethering

  摘要：

  [GRAPHICS]There are only a few methods for the asymmetric ring expansion of prochiral ketones. Symmetrically substituted cyclohexanones can be converted to the corresponding ring expanded caprolactam with excellent 1,7 diastereoselectivity (greater than or equal to 93% ds) and yields (greater than or equal to 86%), using a chiral hydroxy azide-mediated Schmidt reaction.

  DOI：

  10.1021/ol990685b

文献信息

• Amidino dervatives useful as nitric oxide synthase inhibitors
  申请人：G. D. Searle & Co.

  公开号：US05854234A1

  公开（公告）日：1998-12-29

  The current invention discloses useful pharmaceutical compositions containing azepine derivatives useful as nitric oxide synthase inhibitors.

  本发明公开了含有用作一氧化氮合酶抑制剂的氮杂环衍生物的有用药物组合物。
• Amidino derivatives useful as nitric oxide synthase inhibitors
  申请人：G.D. Searle & Co.

  公开号：US06046211A1

  公开（公告）日：2000-04-04

  The current invention discloses useful pharmaceutical compositions containing amidino derivative useful as nitric oxide synthase inhibitors.

  本发明公开了含有作为一氧化氮合酶抑制剂的有用酰胺基衍生物的有用药物组合物。
• 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.
• AUBE, JEFFREY;HAMMOND, MARLYS;GHERARDINI, ELYSE;TAKUSAGAWA, FUSAO, J. ORG. CHEM., 56,(1991) N, C. 499-508
  作者：AUBE, JEFFREY、HAMMOND, MARLYS、GHERARDINI, ELYSE、TAKUSAGAWA, FUSAO

  DOI：——

  日期：——
• AMIDINO DERIVATIVES USEFUL AS NITRIC OXIDE SYNTHASE INHIBITORS
  申请人：G.D. SEARLE & CO.

  公开号：EP0724570A1

  公开（公告）日：1996-08-07