(R)-hexahydro-3-methyl-2H-azepin-2-one | 131613-13-3

• 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-3-methyl-2H-azepin-2-one
• 英文别名: r-Methyl-caprolactam；(3R)-3-methylazepan-2-one
• CAS: 131613-13-3
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: FGSUUFDRDVJCLT-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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

• 作为产物：
  描述：

  -hexahydro-3-methyl-1-(1-phenylethyl)-2H-azepin-2-one 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以86%的产率得到(R)-hexahydro-3-methyl-2H-azepin-2-one
  参考文献：
  名称：

  Syntheses and rearrangements of spirocyclic oxaziridines derived from unsymmetrical ketones

  摘要：

  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.

  DOI：

  10.1021/jo00002a006

文献信息

• Enantioselective Synthesis of 2-Substituted 5-, 6- and 7-Membered Lactams via α-Alkylation of Their Chiral N-Dialkylamino Derivatives
  作者：Dieter Enders、Robert Gröbner、Gerhard Raabe、Jan Runsink

  DOI：10.1055/s-1996-4443

  日期：1996.8

  2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee =71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≥ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e’.

  通过手性N-（二烷基氨基）内酰胺2的α-烷基化反应，随后在液氨中使用锂进行所得内酰胺3的还原性N-N键断裂，合成了具有良好总收率和高对映体纯度（ee = 71-99%）的2-烷基取代内酰胺4。这些内酰胺2是通过将β-氯代烷基酰肼1与氢化钠环合反应制备的，收率良好。内酰胺4的酸性水解得到γ-氨基丁酸（GABA）衍生物5（ee ≥ 99%）。绝对构型通过旋光仪测定和（S，S）-3e’的X射线结构分析确定。
• Use of neurokinin antagonists in the treatment of urinary incontinence
  申请人：Novartis AG

  公开号：EP2158910A1

  公开（公告）日：2010-03-03

  This invention relates to compounds of formula (I), wherein the R1, R2, R3, R4, R5 R6 and R7 are as defined in the specification, and, in particular, their use as pharmaceuticals, e.g. use in urinary incontinence.

  本发明涉及式 (I) 化合物，其中 R1、R2、R3、R4、R5、R6 和 R7 如说明书中所定义，尤其涉及其作为药物的用途，例如用于治疗尿失禁。
• PHOTO-INDUCED RING EXPANSION OF 1-TRIISOPROPYLSILYLOXY-1-AZIDOCYCLOHEXANE: PREPARATION OF ε-CAPROLACTAM
  作者：Nelson, Jade D.、Modi, Dilip P.、Evans, P. Andrew、Foyle, Patrick、Belica, Peter、Wolff, Steven

  DOI：10.15227/orgsyn.079.0165

  日期：——
• 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：——
• Use of acylaminoalkenylene-amide derivatives in functional motility disorders of the viscera
  申请人：Fozard R. John

  公开号：US20070293473A1

  公开（公告）日：2007-12-20

  The use of a compound of formula I in free form or in the form of a pharmaceutically acceptable salt for the preparation of a medicament for the treatment of a functional motility disorder of the viscera.