(2S,2'S)-N,N'-(1,2-phenylenebis(prop-2-yne-3,1-diyl))bis(2-amino-3-methylbutanamide) | 1186404-62-5

• 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: (2S,2'S)-N,N'-(1,2-phenylenebis(prop-2-yne-3,1-diyl))bis(2-amino-3-methylbutanamide)
• CAS: 1186404-62-5
• 化学式: C₂₂H₃₀N₄O₂
• 分子量: 382.506
• InChiKey: YUQBGPSFGCBNSI-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110.24
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-N,N'-(1,2-phenylenebis(prop-2-yne-3,1-diyl))bis(2-amino-3-methylbutanamide) 、 3-二苯基磷烷基苯甲酸 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84.8 mg的产率得到3-diphenylphosphanyl-N-[(2S)-1-[3-[2-[3-[[(2S)-2-[(3-diphenylphosphanylbenzoyl)amino]-3-methylbutanoyl]amino]prop-1-ynyl]phenyl]prop-2-ynylamino]-3-methyl-1-oxobutan-2-yl]benzamide
  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
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-valine N'-propargylamide 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2S,2'S)-N,N'-(1,2-phenylenebis(prop-2-yne-3,1-diyl))bis(2-amino-3-methylbutanamide)
  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

• Synthesis and evaluation of homodimeric GnRHR antagonists having a rigid bis-propargylated benzene core
  作者：Kimberly M. Bonger、Richard J.B.H.N. van den Berg、Annemiek D. Knijnenburg、Laura H. Heitman、Ad P. IJzerman、Julia Oosterom、Cornelis M. Timmers、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1016/j.bmc.2008.01.054

  日期：2008.4.1

  The fact that GPCRs might function in a dimeric fashion is currently well accepted. For GnRHR, a GPCR that regulates gonadotropin release, there is evidence that the receptor also functions as a dimer. We here describe the design and synthesis of a set of dimeric GnRHR antagonists in order to understand the interaction of dimeric ligands to the receptor and to address the question whether GnRHR dimerisation is a prerequisite for signalling. Biological evaluation of the compounds shows no discrimination between monomeric and dimeric ligands in respect to binding affinities, however, the dimeric ligands appear to have different functional properties. (C) 2008 Elsevier Ltd. All rights reserved.