{(1S,2S)-2-[2-((1S,2S)-2-Azido-cyclohexyloxy)-acetylamino]-cyclohexyloxy}-acetic acid tert-butyl ester | 357922-53-3

• 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: {(1S,2S)-2-[2-((1S,2S)-2-Azido-cyclohexyloxy)-acetylamino]-cyclohexyloxy}-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[(1S,2S)-2-[[2-[(1S,2S)-2-azidocyclohexyl]oxyacetyl]amino]cyclohexyl]oxyacetate
• CAS: 357922-53-3
• 化学式: C₂₀H₃₄N₄O₅
• 分子量: 410.514
• InChiKey: GTLHMYMFWYREAB-QAETUUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(1S,2S)-2-[2-((1S,2S)-2-Azido-cyclohexyloxy)-acetylamino]-cyclohexyloxy}-acetic acid tert-butyl ester 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 25.5h， 生成 C₂₄H₃₉N₃O₆
  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)-2-azidocyclohexanol 在 palladium on activated charcoal sodium hydroxide 、 四丁基溴化铵 、 氢气 、 三甲基乙酰氯 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 27.5h， 生成 {(1S,2S)-2-[2-((1S,2S)-2-Azido-cyclohexyloxy)-acetylamino]-cyclohexyloxy}-acetic acid tert-butyl ester
  参考文献：
  名称：

  Cyclohexyletherδ-Amino Acids: New Leads for Selectivity Filters in Ion Channels

  摘要：

  Synthetic ion channels containing δ-amino acids can become cation selective! δ-Amino acids with a cyclohexylether unit were combined with structural motives from gramicidin A and led to channels with a NH4+ /K+ permeability ratio of >10/1. (The current trace for an NH4+ channel is shown.).

  DOI：

  10.1002/1521-3773(20010601)40:11<2076::aid-anie2076>3.0.co;2-g

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.
• Cyclohexyletherδ-Amino Acids: New Leads for Selectivity Filters in Ion Channels
  作者：Hans-Dieter Arndt、Andrea Knoll、Ulrich Koert

  DOI：10.1002/1521-3773(20010601)40:11<2076::aid-anie2076>3.0.co;2-g

  日期：2001.6.1

  Synthetic ion channels containing δ-amino acids can become cation selective! δ-Amino acids with a cyclohexylether unit were combined with structural motives from gramicidin A and led to channels with a NH4+ /K+ permeability ratio of >10/1. (The current trace for an NH4+ channel is shown.).