(E,4S)-4-amino-5-phenylpent-2-en-1-ol | 298208-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,4S)-4-amino-5-phenylpent-2-en-1-ol
• CAS: 298208-80-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: RMRMPYGKBFZZHI-TZOMUSMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,4S)-4-amino-5-phenylpent-2-en-1-ol 在 吡啶 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 38.0h， 生成 (4S-cis)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r
• 作为产物：
  描述：

  (4S)-4-(N-叔丁氧羰基)氨基-5-苯基-2-戊烯-1-醇 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (E,4S)-4-amino-5-phenylpent-2-en-1-ol
  参考文献：
  名称：

  Irreversible inhibitions of serine proteases by peptidyl allylic halide derivatives

  摘要：

  Peptidyl 4-amino-5-phenyl-2-pentenyl bromide (7a, 9a, 10a) and chloride derivatives (7b, 9b, 10b) were found to be active-site directed irreversible inhibitors of alpha-chymotrypsin but did not show any irreversible inhibitory activity toward porcine pancreatic elastase.

  DOI：

  10.1016/0960-894x(95)00592-h