(8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.0_4,8]heneicosane-9,17-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.0_4,8]heneicosane-9,17-dione
• 英文别名: (8S,18S)-1,4,10,13,16-pentazatricyclo[16.3.0.04,8]henicosane-9,17-dione
• 化学式: C₁₆H₂₉N₅O₂
• 分子量: 323.439
• InChiKey: PHCGHIIMHZZQGM-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  76.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丹酰氯 、 (8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.0_4,8]heneicosane-9,17-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以43.49%的产率得到
  参考文献：
  名称：

  A dansyl-appended N-heterocycle for Cu2+ and S2− recognition via a displacement mode

  摘要：

  A novel L-proline based heterocycle 3 of C-2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O = 9:1 (HEPES buffer, 0.01 M, pH 7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2-, even in the presence of S2O32-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of H-1 NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2- was carried out in HeLa cells. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2018.11.017
• 作为产物：
  描述：

  L-脯氨酸甲酯 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 288.0h， 生成 (8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.0_4,8]heneicosane-9,17-dione
  参考文献：
  名称：

  衍生自l-脯氨酸的新型刚性手性大环二氧杂多胺作为羧酸的手性溶剂化剂

  摘要：

  1 H NMR用于研究两种新型的l-脯氨酸衍生的刚性手性大环二氧杂多胺（（12 S）-1,4,7,10-四氮二环[10.3.0] pentadecane-3,11-dione 1的手性识别能力（8 S，18 S）-1,4,10,13,16-五氮杂三环[16.3.0.0 4,8 ] heneicosane-9,17-dione 2，后者是新合成的。通过X射线单晶结构分析确定两种大环化合物的晶体结构。乔布图表明化合物1与（R）-或（S）-扁桃酸形成1：1瞬时络合物，而化合物2与上面的两个客人组成一个1：2的瞬间复合体。通过非线性最小二乘拟合法确定化合物1与（R）-和（S）-扁桃酸的缔合常数。对于我们选择的外消旋羧酸的对映异构体，两个大环均表现出良好的手性识别能力。结果表明，大环dioxopolyamine Ç 2对称性具有比的对映异构体更好识别能力Ç 1对称性。

  DOI：

  10.1016/j.tetasy.2004.07.016

文献信息

• Novel rigid chiral macrocyclic dioxopolyamines derived from l-proline as chiral solvating agents for carboxylic acids
  作者：Xuemei Yang、Xiaojun Wu、Maohai Fang、Quan Yuan、Enqin Fu

  DOI：10.1016/j.tetasy.2004.07.016

  日期：2004.8

  NMR was employed to investigate the chiral recognition ability of two novel l-proline derived rigid chiral macrocyclic dioxopolyamines, (12S)-1,4,7,10-tetraazadicyclo[10.3.0]pentadecane-3,11-dione 1 and (8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.04,8]heneicosane-9,17-dione 2, the latter of which is newly synthesized. The crystal structures of the two macrocyclic compounds were determined by X-ray

  1 H NMR用于研究两种新型的l-脯氨酸衍生的刚性手性大环二氧杂多胺（（12 S）-1,4,7,10-四氮二环[10.3.0] pentadecane-3,11-dione 1的手性识别能力（8 S，18 S）-1,4,10,13,16-五氮杂三环[16.3.0.0 4,8 ] heneicosane-9,17-dione 2，后者是新合成的。通过X射线单晶结构分析确定两种大环化合物的晶体结构。乔布图表明化合物1与（R）-或（S）-扁桃酸形成1：1瞬时络合物，而化合物2与上面的两个客人组成一个1：2的瞬间复合体。通过非线性最小二乘拟合法确定化合物1与（R）-和（S）-扁桃酸的缔合常数。对于我们选择的外消旋羧酸的对映异构体，两个大环均表现出良好的手性识别能力。结果表明，大环dioxopolyamine Ç 2对称性具有比的对映异构体更好识别能力Ç 1对称性。
• Rational design of an “on-off-on” fluorescent switch for Cu2+ and histidine based on chiral macrocyclic dioxopolyamine
  作者：Xiaohuan Huang、Kaiqun Li、Xu Wang、Peng Xia

  DOI：10.1016/j.saa.2018.07.042

  日期：2018.12

  A novel chemosensor 1 having a chiral macrocyclic dioxopolyamine of C2 symmetry as a receptor and anthracene as a signal unit has been designed and synthesized for cations and α-amino acids recognition in DMSO-HEPES buffer (1:9, v/v, pH 7.2). The ligand exhibited selective response to Cu2+ even in the presence of other metal ions with a fluorescence “switch-off” behavior. Additionally, the in situ

  设计并合成了一种新型化学传感器1，该化合物具有C 2对称性的手性大环二氧杂胺作为受体，蒽作为信号单元，用于在DMSO-HEPES缓冲液（1：9，v / v，pH）中识别阳离子和α-氨基酸。 7.2）。即使在存在其他具有荧光“关闭”行为的金属离子的情况下，配体也表现出对Cu 2+的选择性响应。此外，原位生成的1-Cu 2+集合体通过“接通”荧光响应显示出对组氨酸的特异性识别。对于此双功能开关，其通过位移模式的感应行为已通过以下方式得到确认：1 H NMR滴定和ESI质谱。1对Cu 2+和组氨酸的顺序“ on-off-on”荧光反应已成功应用于HeLa细胞。
• A dansyl-appended N-heterocycle for Cu2+ and S2− recognition via a displacement mode
  作者：Xu Wang、Peng Xia、Xiaohuan Huang

  DOI：10.1016/j.saa.2018.11.017

  日期：2019.3

  A novel L-proline based heterocycle 3 of C-2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O = 9:1 (HEPES buffer, 0.01 M, pH 7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2-, even in the presence of S2O32-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of H-1 NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2- was carried out in HeLa cells. (C) 2018 Elsevier B.V. All rights reserved.
• Synthesis of Novel L‐Proline Derived Macrocyclic Dioxopolyamines of C₂Symmetry
  作者：Xuemei Yang、Baohua Li、Enqin Fu

  DOI：10.1081/scc-200048458

  日期：2005.1

  A short and convenient synthesis for four novel chiral L‐proline derived macrocyclic dioxopolyamines of C2 symmetry, by condensation of appropriate diester intermediates and polyamines, is reported. These macrocyclic dioxopolyamines may be applied as chiral solvating agents for enantiomeric recognition, and the work also provided a simple and convenient way for the synthesis of the diester intermediates

  摘要 报道了通过适当的二酯中间体和多胺的缩合，短而方便地合成了四种新型手性 L-脯氨酸衍生的 C2 对称的大环二氧多胺。这些大环二氧多胺可作为手性溶剂化剂用于对映体识别，该工作也为二酯中间体的合成提供了一种简便的途径。