methyl (2S,3aR,6R,7aR)-1-benzyl-6-hydroxyoctahydroindole-2-carboxylate | 501368-62-3

• 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: methyl (2S,3aR,6R,7aR)-1-benzyl-6-hydroxyoctahydroindole-2-carboxylate
• 英文别名: methyl (2S,3aR,6R,7aR)-1-benzyl-6-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate
• CAS: 501368-62-3
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: CRKDJTMHMPQZPT-FPCVCCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aR,6R,7aR)-1-benzyl-6-hydroxyoctahydroindole-2-carboxylate 在 palladium dihydroxide N-甲基吗啉 、 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 100.0h， 生成
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250
• 作为产物：
  描述：

  methyl (2S,3aR,7aR)-1-benzyl-6-oxo-octahydroindole-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以72%的产率得到methyl (2S,3aR,6R,7aR)-1-benzyl-6-hydroxyoctahydroindole-2-carboxylate
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250