(S,S)-N,N'-bis(alanyl)-1,3-diaminopropane | 110449-66-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (S,S)-N,N'-bis(alanyl)-1,3-diaminopropane
• 英文别名: N,N'-Bis(L-alanyl)-1,3-propandiamin；AlaA3；(2S)-2-amino-N-[3-[[(2S)-2-aminopropanoyl]amino]propyl]propanamide
• CAS: 110449-66-6
• 化学式: C₉H₂₀N₄O₂
• 分子量: 216.283
• InChiKey: WJGZGFKXFJXPBA-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-二苯基磷烷基苯甲酸 、 (S,S)-N,N'-bis(alanyl)-1,3-diaminopropane 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107.9 mg的产率得到3-diphenylphosphanyl-N-[(2S)-1-[3-[[(2S)-2-[(3-diphenylphosphanylbenzoyl)amino]propanoyl]amino]propylamino]-1-oxopropan-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,N'-Bis(Z-ala)-1,3-propandiamin 在 氢溴酸 、 溶剂黄146 作用下， 生成 (S,S)-N,N'-bis(alanyl)-1,3-diaminopropane
  参考文献：
  名称：

  具有氨基酸酰胺的金属配合物。四、钯、镍和铜配合物与顺式双（氨基甲酰胺基）金属 (II) 型的 CD 光谱之间的关系

  摘要：

  [ML] 型方形平面配合物，其中 M=Pd2+、Ni2+ 和 Cu2+，对于 L=N,N'-双(L-丙氨酰)-1,3-丙二酸根阴离子，M=Ni2+ 和 Cu2+ 对于 L=N，合成了 N'-双（L-丙氨酰基）-1,2-乙二胺阴离子。在水溶液、乙醇和 DMF 溶液中测量了它们的吸收和 CD 光谱。将结果与顺式和反式双（氨基甲酰胺基）络合物的结果进行比较讨论。在 N,N'-bis(L-alanyl)-1,3-propanediaminatopalladium(II) 及其镍类似物的组分 dd 带之间发现了明确的对应关系，与相应的 trans-bis( L-氨基甲酰胺基）复合物。通过将它们的 CD 数据与钯和镍类似物的 CD 数据进行比较，重新检查了双（氨基甲酰胺）型铜配合物的组分 dd 带的分配。

  DOI：

  10.1246/bcsj.52.1832

文献信息

• ARMANI, ELISABETTA;DOSSENA, ARNALDO;MARCHELLI, ROSANGELA;VIRGILI, ROBERTA, J. CHROMATOGR., 441,(1988) N 2, 275-286
  作者：ARMANI, ELISABETTA、DOSSENA, ARNALDO、MARCHELLI, ROSANGELA、VIRGILI, ROBERTA

  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.
• Metal Complexes with Amino Acid Amides. IV. Relationship between the CD Spectra of Palladium, Nickel, and Copper Complexes with<i>cis</i>-Bis(amino carboxamidato) metal(II) Type
  作者：Takashi Komorita、Yoichi Shimura

  DOI：10.1246/bcsj.52.1832

  日期：1979.6

  3-propanediaminatopalladium(II) and those of its nickel analog, in line with a similar correspondence for the corresponding trans-bis(L-amino carboxamidato) complexes. Assignment of the component d-d bands has been reexamined for the copper complexes of bis (amino carboxamidato) type by comparing their CD data with those for the palladium and nickel analogs.

  [ML] 型方形平面配合物，其中 M=Pd2+、Ni2+ 和 Cu2+，对于 L=N,N'-双(L-丙氨酰)-1,3-丙二酸根阴离子，M=Ni2+ 和 Cu2+ 对于 L=N，合成了 N'-双（L-丙氨酰基）-1,2-乙二胺阴离子。在水溶液、乙醇和 DMF 溶液中测量了它们的吸收和 CD 光谱。将结果与顺式和反式双（氨基甲酰胺基）络合物的结果进行比较讨论。在 N,N'-bis(L-alanyl)-1,3-propanediaminatopalladium(II) 及其镍类似物的组分 dd 带之间发现了明确的对应关系，与相应的 trans-bis( L-氨基甲酰胺基）复合物。通过将它们的 CD 数据与钯和镍类似物的 CD 数据进行比较，重新检查了双（氨基甲酰胺）型铜配合物的组分 dd 带的分配。