(1'S,2'S)-(2'-azido-cyclohexyl)oxy-acetic-acid-tert-butylester | 357922-50-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1'S,2'S)-(2'-azido-cyclohexyl)oxy-acetic-acid-tert-butylester
• 英文别名: tert-butyl 2-[(1S,2S)-2-azidocyclohexyl]oxyacetate
• CAS: 357922-50-0
• 化学式: C₁₂H₂₁N₃O₃
• 分子量: 255.317
• InChiKey: BVJOYTHEVCOMFP-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,2'S)-(2'-azido-cyclohexyl)oxy-acetic-acid-tert-butylester 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 C₃₂H₅₂N₄O₈
  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：

  cyclohexene oxide 在 sodium hydroxide 、 [Cr(N₃)salen] 、 四丁基溴化铵 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 异丙醇 、 甲苯 为溶剂， 反应 61.0h， 生成 (1'S,2'S)-(2'-azido-cyclohexyl)oxy-acetic-acid-tert-butylester
  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.).