tert-butyl (3S,6S,9aS)-6-amino-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate | 188127-62-0

• 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: tert-butyl (3S,6S,9aS)-6-amino-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
• 英文别名: tert-butyl (3S,6S,9aS)-6-amino-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
• CAS: 188127-62-0
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: ATNIMEJQUKXJFA-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,6S,9aS)-6-amino-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 在 哌啶 、 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 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 氯仿 、 叔丁基氯化镁 、 氢溴酸 、 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 水 、 乙腈 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 124.0h， 生成 tert-butyl (3S,6S,9aS)-6-amino-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.09.037

文献信息

• Synthesis of Functionalized Azabicycloalkane Amino Acids as Dipeptide Mimics
  作者：Leonardo Manzoni、Carlo Scolastico、Laura Belvisi、Eliana DiCarlo、Alessandra Forni、Donatella Invernizzi

  DOI：10.1055/s-2006-926370

  日期：——

  Functionalized bicyclic lactams serve as building blocks for the synthesis of conformationally constrained peptides. A route to these building blocks is described based on the stereoselective alkylation of an appropriate azabicycloalkane; all possible diastereoisomers can be obtained stereoselectively.

  功能化的双环内酰胺用作合成构象受限肽的构件。基于合适的氮杂双环烷烃的立体选择性烷基化描述了获得这些结构单元的途径；所有可能的非对映异构体都可以立体选择性地获得。
• NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Buckman Brad

  公开号：US20110312996A1

  公开（公告）日：2011-12-22

  The embodiments provide compounds of the general Formulae VI, VII, VIII, IX, X, XI, XII, XIII, XIV, and XV as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  本实施例提供了通式VI、VII、VIII、IX、X、XI、XII、XIII、XIV和XV的化合物，以及包括药物组合物在内的组合物。本实施例还提供了治疗方法，包括治疗丙型肝炎病毒感染和肝纤维化的方法，通常涉及向需要的个体施用所述化合物或组合物的有效量。
• 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.
• Genarri, Cesare; Mielgo, Antonia; Potenza, Donatella, European Journal of Organic Chemistry, 1999, # 2, p. 379 - 388
  作者：Genarri, Cesare、Mielgo, Antonia、Potenza, Donatella、Scolastico, Carlo、Piarulli, Umberto、Manzoni, Leonardo

  DOI：——

  日期：——
• [EN] BICYCLIC LACTAM DERIVATIVES AS THROMBIN INHIBITORS<br/>[FR] DERIVES LACTAMES BICYCLIQUES UTILISES COMME INHIBITEURS DE THROMBINE
  申请人：A. MENARINI INDUSTRIE FARMACEUTICHE RIUNITE S.R.L.

  公开号：WO1997005160A1

  公开（公告）日：1997-02-13

  (EN) Bicyclic lactams containing an arginine residue, which can be of use in therapy as thrombin inhibitors, are disclosed.(FR) L'invention porte sur des lactames bicycliques contenant un reste arginine qui peuvent être utilisés, dans un traitement, comme inhibiteurs de thrombine.