(2R,1'S,2'S)-2-(2'-carboxybenzylamino-cyclohexyl)oxy-3-phenyl-propionic acid | 777939-71-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,1'S,2'S)-2-(2'-carboxybenzylamino-cyclohexyl)oxy-3-phenyl-propionic acid
• 英文别名: (2R)-3-phenyl-2-[(1S,2S)-2-(phenylmethoxycarbonylamino)cyclohexyl]oxypropanoic acid
• CAS: 777939-71-6
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: IJEAOBKDBRCKGI-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,1'S,2'S)-2-(2'-carboxybenzylamino-cyclohexyl)oxy-3-phenyl-propionic acid 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 (1S,3R,6S,11S,16S,21S,26S)-3-benzyl-2,12,22-trioxa-5,15,25-triazatetracyclo[24.4.0.06,11.016,21]triacontane-4,14,24-trione
  参考文献：
  名称：

  Folding Propensity of Cyclohexylether-δ-peptides

  摘要：

  Linear (n = 2-18) and cyclic oligomers (n = 3-8) of a cyclohexylether-delta-amino acid (COA) were prepared in high yield and stereopurity. CID spectra of the linear oligomers were indicative of secondary structure formation. X-ray crystal structures of cyclic COA oligomers revealed hydrophobic packing and internal 5- and 10-membered-ring hydrogen bonds. Ether and amide oxygens reside preferably in an ap orientation. This conformational locking is apparently broken by a C-2 substituent in an asymmetric cyclotrimer, for which a zeolithe-like tubular structure was found.

  DOI：

  10.1021/ol048861q
• 作为产物：
  描述：

  (1S,2S)-反式-1,3-氨基环己醇盐酸盐 在 lithium hydroxide 、 正丁基锂 、 potassium tert-butylate 、 双氧水 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 21.75h， 生成 (2R,1'S,2'S)-2-(2'-carboxybenzylamino-cyclohexyl)oxy-3-phenyl-propionic acid
  参考文献：
  名称：

  Folding Propensity of Cyclohexylether-δ-peptides

  摘要：

  Linear (n = 2-18) and cyclic oligomers (n = 3-8) of a cyclohexylether-delta-amino acid (COA) were prepared in high yield and stereopurity. CID spectra of the linear oligomers were indicative of secondary structure formation. X-ray crystal structures of cyclic COA oligomers revealed hydrophobic packing and internal 5- and 10-membered-ring hydrogen bonds. Ether and amide oxygens reside preferably in an ap orientation. This conformational locking is apparently broken by a C-2 substituent in an asymmetric cyclotrimer, for which a zeolithe-like tubular structure was found.

  DOI：

  10.1021/ol048861q

文献信息

• Folding Propensity of Cyclohexylether-δ-peptides
  作者：Hans-Dieter Arndt、Burkhard Ziemer、Ulrich Koert

  DOI：10.1021/ol048861q

  日期：2004.9.1

  Linear (n = 2-18) and cyclic oligomers (n = 3-8) of a cyclohexylether-delta-amino acid (COA) were prepared in high yield and stereopurity. CID spectra of the linear oligomers were indicative of secondary structure formation. X-ray crystal structures of cyclic COA oligomers revealed hydrophobic packing and internal 5- and 10-membered-ring hydrogen bonds. Ether and amide oxygens reside preferably in an ap orientation. This conformational locking is apparently broken by a C-2 substituent in an asymmetric cyclotrimer, for which a zeolithe-like tubular structure was found.