(1'R,4S)-hexahydro-4-benzyl-1-(1'-phenylethyl)-2H-azepin-2-one | 341508-47-2

• 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: (1'R,4S)-hexahydro-4-benzyl-1-(1'-phenylethyl)-2H-azepin-2-one
• 英文别名: (4S)-4-benzyl-1-[(1R)-1-phenylethyl]azepan-2-one
• CAS: 341508-47-2
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: CYYXKIWIHRLETL-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1'R,4S)-hexahydro-4-benzyl-1-(1'-phenylethyl)-2H-azepin-2-one 在 盐酸 、 氯化亚砜 、 氨 、 sodium 、 1-羟基苯并三唑 、 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 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S)-3-benzyl-6-[N-(tert-butoxycarbonyl)-glycyl-glycyl]-aminohexanoic acid methyl ester
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b
• 作为产物：
  描述：

  [2R(R*)]-2-(1'-phenylethyl)-5-phenylmethyl-1-oxa-2-azaspiro[2.5]octane 反应 19.0h， 生成 (1'R,4S)-hexahydro-4-benzyl-1-(1'-phenylethyl)-2H-azepin-2-one 、 (1'R,6R)-hexahydro-6-benzyl-1-(1'-phenylethyl)-2H-azepin-2-one
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b

文献信息

• Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides
  作者：Mary MacDonald、David Vander Velde、Jeffrey Aubé

  DOI：10.1021/jo001308b

  日期：2001.4.1

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.