ethyl (2R)-5-bromo-6-methoxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-dihydroindene-2-carboxylate | 1207065-38-0

• 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: ethyl (2R)-5-bromo-6-methoxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-dihydroindene-2-carboxylate
• CAS: 1207065-38-0
• 化学式: C₂₇H₃₃BrN₂O₆
• 分子量: 561.473
• InChiKey: PRBNOMQKVNDWFH-IDISGSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (2R)-5-bromo-6-methoxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-dihydroindene-2-carboxylate 反应 0.33h， 以58%的产率得到(2R,5'S)-5'-benzyl-5-bromo-6-methoxyspiro[indane-2,2'-piperazine]-3',6'-dione
  参考文献：
  名称：

  A synchrotron study of (2R,5′S)-5′-benzyl-5-bromo-6-methoxyspiro[indane-2,2′-piperazine]-3′,6′-dione dimethylformamide solvate

  摘要：

  Synchrotron radiation was used to study the structure of the title compound, C(20)H(19)BrN(2)O(3)center dot C(3)H(7)NO, which was obtained as fine fragile needle-shaped crystals by recrystallization from dimethylformamide (DMF), one molecule of which is incorporated per asymmetric unit into the crystal. The compound adopts a compact closed conformation with the orientation of the benzyl group such that the aryl ring is positioned over the piperazinedione ring, resulting in a C(spiro)center dot center dot center dot C(trans)-C-C(Ph) pseudo-torsion angle of -3.3 (3)degrees. The five-membered ring is present in an expected envelope conformation and the six-membered piperazinedione ring adopts a less puckered boat-like conformation. Reciprocal amide-to-amide hydrogen bonding between adjacent piperazinedione rings and C-H center dot center dot center dot O interactions involving DMF molecules propagate in the crystal as a thick ribbon in the a-axis direction.

  DOI：

  10.1107/s0108270110017579
• 作为产物：
  描述：

  ethyl 2-amino-5-bromo-6-methoxyindane-2-carboxylate 、 BOC-L-苯丙氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ethyl (2R)-5-bromo-6-methoxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-dihydroindene-2-carboxylate 、 ethyl (2S)-5-bromo-6-methoxy-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-dihydroindene-2-carboxylate
  参考文献：
  名称：

  Synthesis of the Conformationally Constrained Tyrosine Analogues, (R)- and (S)-5-Hydroxy-2-aminoindan-2-carboxylic Acids

  摘要：

  The conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids, were prepared by chromatographic separation of diastereomeric dipeptide derivatives formed from N-BOC-L-phenylalanine. Absolute configurations were assigned by X-ray crystallographic analysis.

  DOI：

  10.1021/jo902438s