2-[2-[(2-Methoxy-2-oxoethyl)amino]ethyl]-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid | 1026057-55-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-[(2-Methoxy-2-oxoethyl)amino]ethyl]-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid
• CAS: 1026057-55-5
• 化学式: C₁₉H₂₆N₂O₆
• 分子量: 378.425
• InChiKey: HCKIEIBIBLLBMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-[(2-Methoxy-2-oxoethyl)amino]ethyl]-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and x-ray crystallographic analysis of two novel spirolactam systems as .beta.-turn mimics

  摘要：

  Two novel 5.4-spirolactam systems have been developed as beta-turn mimics. The (R)-5.4-spirolactam system of 4 was designed to mimic the type-II beta-turn, and the (S)-5.4-spirolactam system of 5 was designed to mimic the type-II' beta-turn. The 5.4-spirolactam dipeptide mimic 11 was synthesized in racemic form from pipecolic acid. This intermediate was then converted to the diastereoisomeric mixture of peptidomimetics 4 and 5, which were separated by fractional recrystallization. X-ray crystallographic analysis of 4 and 5 indicated that both of these compounds adopted hydrogen-bonded beta-turn conformations. As predicted, the (R)-5.4-spirolactam system of 4 induced a type-II beta-turn while the (S)-5.4-spirolactam system of 5 induced a type-II' beta-turn. The backbone torsion angles of 4 and 5 were close to those of the classical type-II and-II' beta-turns, respectively. A computer-generated fit between nine atoms of the backbone of 4 and their counterparts in an ideal type-II beta-turn yielded an RMS fit of 0.218 angstrom. A similar comparison between 5 and an ideal type-II' beta-turn produced an RMS fit of 0.392 angstrom.

  DOI：

  10.1021/jo00056a018
• 作为产物：
  描述：

  六氢吡啶-alpha-羧酸 在 sodium hydroxide 、 sodium periodate 、 四氧化锇 、 3 A molecular sieve 、 硫酸 、 水 、 sodium cyanoborohydride 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 57.25h， 生成 2-[2-[(2-Methoxy-2-oxoethyl)amino]ethyl]-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and x-ray crystallographic analysis of two novel spirolactam systems as .beta.-turn mimics

  摘要：

  Two novel 5.4-spirolactam systems have been developed as beta-turn mimics. The (R)-5.4-spirolactam system of 4 was designed to mimic the type-II beta-turn, and the (S)-5.4-spirolactam system of 5 was designed to mimic the type-II' beta-turn. The 5.4-spirolactam dipeptide mimic 11 was synthesized in racemic form from pipecolic acid. This intermediate was then converted to the diastereoisomeric mixture of peptidomimetics 4 and 5, which were separated by fractional recrystallization. X-ray crystallographic analysis of 4 and 5 indicated that both of these compounds adopted hydrogen-bonded beta-turn conformations. As predicted, the (R)-5.4-spirolactam system of 4 induced a type-II beta-turn while the (S)-5.4-spirolactam system of 5 induced a type-II' beta-turn. The backbone torsion angles of 4 and 5 were close to those of the classical type-II and-II' beta-turns, respectively. A computer-generated fit between nine atoms of the backbone of 4 and their counterparts in an ideal type-II beta-turn yielded an RMS fit of 0.218 angstrom. A similar comparison between 5 and an ideal type-II' beta-turn produced an RMS fit of 0.392 angstrom.

  DOI：

  10.1021/jo00056a018

文献信息

• Design, synthesis, and x-ray crystallographic analysis of two novel spirolactam systems as .beta.-turn mimics
  作者：Michael J. Genin、William B. Gleason、Rodney L. Johnson

  DOI：10.1021/jo00056a018

  日期：1993.2

  Two novel 5.4-spirolactam systems have been developed as beta-turn mimics. The (R)-5.4-spirolactam system of 4 was designed to mimic the type-II beta-turn, and the (S)-5.4-spirolactam system of 5 was designed to mimic the type-II' beta-turn. The 5.4-spirolactam dipeptide mimic 11 was synthesized in racemic form from pipecolic acid. This intermediate was then converted to the diastereoisomeric mixture of peptidomimetics 4 and 5, which were separated by fractional recrystallization. X-ray crystallographic analysis of 4 and 5 indicated that both of these compounds adopted hydrogen-bonded beta-turn conformations. As predicted, the (R)-5.4-spirolactam system of 4 induced a type-II beta-turn while the (S)-5.4-spirolactam system of 5 induced a type-II' beta-turn. The backbone torsion angles of 4 and 5 were close to those of the classical type-II and-II' beta-turns, respectively. A computer-generated fit between nine atoms of the backbone of 4 and their counterparts in an ideal type-II beta-turn yielded an RMS fit of 0.218 angstrom. A similar comparison between 5 and an ideal type-II' beta-turn produced an RMS fit of 0.392 angstrom.