tert-butyl (3S,6S,9aS)-6-(2,2,2-trifluoroacetylamino)-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate | 643014-05-5

• 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: tert-butyl (3S,6S,9aS)-6-(2,2,2-trifluoroacetylamino)-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
• 英文别名: tert-butyl (3S,6S,9aS)-5-oxo-6-[(2,2,2-trifluoroacetyl)amino]-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
• CAS: 643014-05-5
• 化学式: C₁₆H₂₃F₃N₂O₄
• 分子量: 364.365
• InChiKey: TVZUETSKWBDFHW-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,6S,9aS)-6-(2,2,2-trifluoroacetylamino)-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 在 哌啶 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

  Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins

  摘要：

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.170
• 作为产物：
  描述：

  methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate 在 palladium on activated charcoal 叔丁基氯化镁 、 氢溴酸 、 氢气 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 氯仿 、 乙腈 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 50.0h， 生成 tert-butyl (3S,6S,9aS)-6-(2,2,2-trifluoroacetylamino)-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

  Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins

  摘要：

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.170

文献信息

• Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins
  作者：David E. Davies、Paul M. Doyle、R.Duncan Farrant、Richard D. Hill、Peter B. Hitchcock、Paul N. Sanderson、Douglas W. Young

  DOI：10.1016/j.tetlet.2003.09.170

  日期：2003.12

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of an external beta-turn based on the GLDV motif of cell adhesion proteins
  作者：David E. Davies、Paul M. Doyle、Richard D. Hill、Douglas W. Young

  DOI：10.1016/j.tet.2004.09.037

  日期：2005.1

  The (3S,6S, 10S)-7/5 bicyclic lactam 8, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. The cyclic peptide 35 containing the integrin recognition motif GLDV added across the amino and carboxyl groups of the lactam external constraint 8 was prepared. (C) 2004 Elsevier Ltd. All rights reserved.