(S)-thpec12 | 205066-94-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-thpec12
• CAS: 205066-94-0
• 化学式: C₄₀H₅₂N₄O₄
• 分子量: 652.877
• InChiKey: XGENMCFBPIVUMO-YKKXUYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.88
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  cadmium(II) perchlorate hexahydrate 、 (S)-thpec12 以 乙醇 为溶剂， 以99%的产率得到(Cd((S)-thpec12))(ClO4)2
  参考文献：
  名称：

  Metal Ion-Dependent Molecular Inclusion Chemistry:  Inclusion of Aromatic Anions by Coordinated 1,4,7,10-Tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane

  摘要：

  The ability of the pendant donor macrocyclic ligand 1,4,7,10-tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane((S)-thphpc12) (or [Cd((S)-thphpc12)](2+)) to act as a metal ion-dependent receptor for aromatic anions has been investigated in solution and in the solid state. [Cd((S)-thphpc12)](2+) adopts a stable conical conformation with a large hydrophobic cavity, which has been shown to contain, via complementary multiple hydrogen bonding, p-nitrophenolate, aromatic carboxylates, p-toluenesulfonate, certain aromatic amino acid anions, phenoxyacetate, and acetate. In the case of p-nitrophenolate only, one or two anions can be contained within the receptor cavity. The crystal structure of [Cd((S)-thphpc12)(p-nitrophenolate)(2)] shows a coplanar arrangement of the p-nitrophenolates, where each is retained in the cavity by a pair of hydrogen bonds to cis hydroxyl groups. The crystal structure of the p-aminobenzoate inclusion complex indicates retention of the guest via a pair of hydrogen bonds to each oxygen atom of the carboxylate moiety, The crystal structure of the (L)-phenylalaninate inclusion complex indicates that the amino acid is retained by five hydrogen bonds, two involving the nitrogen atom and three to the oxygen atoms of the carboxylate moiety. Binding constants (10(3)-10(5) M-1) for the inclusion of some of the aforementioned anions in [Cd((S)-thphpc12)](2+) and related receptors were measured by H-1 NIVR titration in DMSO-d(6) at 298 K.

  DOI：

  10.1021/ic010694s
• 作为产物：
  描述：

  (R)-环氧苯乙烷 、 轮环藤宁 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以61%的产率得到(S)-thpec12
  参考文献：
  名称：

  非对映异构 Δ-1,4,7,10-Tetrakis((R)-2-hydroxy-2-phenylethyl)-1,4,7,10-tetraazacyclododecane 及其碱金属复合离子。电位滴定、核磁共振和分子轨道研究

  摘要：

  13C NMR研究与Δ-1,4,7,10-四((R)-2-羟基-2-苯乙基)-1,4,7,10-四氮杂环十二烷(ΔR-thpec12)及其八坐标一致碱金属配合物 Δ[M(R-thpec12)]+，主要以单方形反棱柱 Δ 非对映异构体形式存在于二甲基甲酰胺中。分子轨道计算显示平行的方形氧和氮平面描绘了 ΔR-thpec12 和 Δ[M(R-thpec12)]+ 的方形反棱柱结构，其中由 ΔR-thpec12 的四个苯基定义的篮子变得越来越浅M+ 半径从 Na+ 增加到 Cs+，四个氧进一步分开。涉及所有四个氮中心的双重反转的分子内交换过程发生在 ΔR-thpec12 中，其中 k(298.2 K) = 46300 ± 1800 s-1，ΔH⧧ = 40.8 ± 0.4 kJ mol-1，ΔS⧧ = - 18.8 ± 1.7 J K-1 mol-1。

  DOI：

  10.1021/ja973367l