1,2-di-((2R,5R)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-on-5-yl)ethane | 881032-74-2

• 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: 1,2-di-((2R,5R)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-on-5-yl)ethane
• 英文别名: (3R,7aR)-7a-[2-[(3R,7aR)-3-tert-butyl-1-oxo-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-7a-yl]ethyl]-3-tert-butyl-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-one
• CAS: 881032-74-2
• 化学式: C₂₂H₃₆N₂O₄
• 分子量: 392.539
• InChiKey: POBXWCQCFYQYGP-AHWCRGGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-di-((2R,5R)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-on-5-yl)ethane 在 N-甲基吗啉 、 盐酸 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 生成 (2R,2'R)-2,2'-ethano-cyclo(Pro-Pro)
  参考文献：
  名称：

  Concerted Synthesis of a Spirobicyclic Type-VI β-Turn Mimic of Pro-Pro-Pro-NH₂

  摘要：

  A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i + 1 and i + 2 residues are identical.

  DOI：

  10.1021/ol0600335
• 作为产物：
  描述：

  甲磺酸,三氟-,1,2-乙二基酯 、 (2R,5S)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以76%的产率得到1,2-di-((2R,5R)-2-tert-butyl-1-aza-3-oxabicyclo[3.3.0]octan-4-on-5-yl)ethane
  参考文献：
  名称：

  Concerted Synthesis of a Spirobicyclic Type-VI β-Turn Mimic of Pro-Pro-Pro-NH₂

  摘要：

  A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i + 1 and i + 2 residues are identical.

  DOI：

  10.1021/ol0600335

文献信息

• Concerted Synthesis of a Spirobicyclic Type-VI β-Turn Mimic of Pro-Pro-Pro-NH₂
  作者：Ashish P. Vartak、Rodney L. Johnson

  DOI：10.1021/ol0600335

  日期：2006.3.2

  A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i + 1 and i + 2 residues are identical.