tert-butyl N-[(2S)-1-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butylamino]-1-oxopropan-2-yl]carbamate | 1026551-34-7

• 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 N-[(2S)-1-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butylamino]-1-oxopropan-2-yl]carbamate
• CAS: 1026551-34-7
• 化学式: C₂₀H₃₈N₄O₆
• 分子量: 430.545
• InChiKey: CKYZVKWRDUENEE-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butylamino]-1-oxopropan-2-yl]carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Lyakhov; Suveyzdis; Litvinova, Pharmazie, 2000, vol. 55, # 10, p. 733 - 736

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 四亚甲基二胺 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以65%的产率得到tert-butyl N-[(2S)-1-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butylamino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  “Backdoor Induction” of Chirality: Asymmetric Hydrogenation with Rhodium(I) Complexes of Triphenylphosphane-Substituted β-Turn Mimetics

  摘要：

  Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based beta-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by "backdoor induction" from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.

  DOI：

  10.1021/om5005385

文献信息

• Lyakhov; Suveyzdis; Litvinova, Pharmazie, 2000, vol. 55, # 10, p. 733 - 736
  作者：Lyakhov、Suveyzdis、Litvinova、Andronati、Rybalko、Dyadyun

  DOI：——

  日期：——
• “Backdoor Induction” of Chirality: Asymmetric Hydrogenation with Rhodium(I) Complexes of Triphenylphosphane-Substituted β-Turn Mimetics
  作者：Zoran Kokan、Zoran Glasovac、Maja Majerić Elenkov、Matija Gredičak、Ivanka Jerić、Srećko I. Kirin

  DOI：10.1021/om5005385

  日期：2014.8.11

  Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based beta-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by "backdoor induction" from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.