Pyridine-2,6-dicarboxylic acid 2-{(S)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester 6-[(R)-1-(6-hydroxymethyl-pyridin-2-yl)-ethyl] ester | 207735-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Pyridine-2,6-dicarboxylic acid 2-{(S)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester 6-[(R)-1-(6-hydroxymethyl-pyridin-2-yl)-ethyl] ester
• 英文别名: 6-O-[(1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethyl] 2-O-[(1R)-1-[6-(hydroxymethyl)pyridin-2-yl]ethyl] pyridine-2,6-dicarboxylate
• CAS: 207735-42-0
• 化学式: C₂₉H₃₇N₃O₆Si
• 分子量: 551.715
• InChiKey: BPSBZKYMEOLHHJ-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 Pyridine-2,6-dicarboxylic acid 2-{(S)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester 6-[(R)-1-(6-hydroxymethyl-pyridin-2-yl)-ethyl] ester 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到Pyridine-2,6-dicarboxylic acid 2-{(R)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester 6-{(S)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester
  参考文献：
  名称：

  Ag⁺-Specific Pyridine Podands:  Effects of Ligand Geometry and Stereochemically Controlled Substitution on Cation Complexation and Transport Functions

  摘要：

  A new series of acyclic podands was designed so that three pyridine moieties cooperatively bind a guest Ag(+). Liquid-Liquid extraction, NMR binding, and computer calculation experiments reveal that podands with three pyridine donors in a proper geometry exhibit a perfect Ag(+) specificity. They selectively extracted Ag+ in the presence of equimolar Pb(2+), CU(2+), Ni(2+), Co(2+), and Zn(2+). Introduction of two chiral centers close to the pyridine binding sites surprisingly influences the Ag(+)-binding ability of the podand. Fourteen new pyridine podands were evaluated as carriers in a liquid membrane transport system. A combination of ligand geometry and stereocontrolled substitution provides excellent Ag(+)-specific transport.

  DOI：

  10.1021/jo9721148
• 作为产物：
  描述：

  6-O-[(1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethyl] 2-O-[(1R)-1-[6-(trityloxymethyl)pyridin-2-yl]ethyl] pyridine-2,6-dicarboxylate 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以88%的产率得到Pyridine-2,6-dicarboxylic acid 2-{(S)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl} ester 6-[(R)-1-(6-hydroxymethyl-pyridin-2-yl)-ethyl] ester
  参考文献：
  名称：

  Ag⁺-Specific Pyridine Podands:  Effects of Ligand Geometry and Stereochemically Controlled Substitution on Cation Complexation and Transport Functions

  摘要：

  A new series of acyclic podands was designed so that three pyridine moieties cooperatively bind a guest Ag(+). Liquid-Liquid extraction, NMR binding, and computer calculation experiments reveal that podands with three pyridine donors in a proper geometry exhibit a perfect Ag(+) specificity. They selectively extracted Ag+ in the presence of equimolar Pb(2+), CU(2+), Ni(2+), Co(2+), and Zn(2+). Introduction of two chiral centers close to the pyridine binding sites surprisingly influences the Ag(+)-binding ability of the podand. Fourteen new pyridine podands were evaluated as carriers in a liquid membrane transport system. A combination of ligand geometry and stereocontrolled substitution provides excellent Ag(+)-specific transport.

  DOI：

  10.1021/jo9721148

文献信息

• Ag⁺-Specific Pyridine Podands:  Effects of Ligand Geometry and Stereochemically Controlled Substitution on Cation Complexation and Transport Functions
  作者：Hiroshi Tsukube、Satoshi Shinoda、Jun'ichi Uenishi、Takao Hiraoka、Takahiro Imakoga、Osamu Yonemitsu

  DOI：10.1021/jo9721148

  日期：1998.6.1

  A new series of acyclic podands was designed so that three pyridine moieties cooperatively bind a guest Ag(+). Liquid-Liquid extraction, NMR binding, and computer calculation experiments reveal that podands with three pyridine donors in a proper geometry exhibit a perfect Ag(+) specificity. They selectively extracted Ag+ in the presence of equimolar Pb(2+), CU(2+), Ni(2+), Co(2+), and Zn(2+). Introduction of two chiral centers close to the pyridine binding sites surprisingly influences the Ag(+)-binding ability of the podand. Fourteen new pyridine podands were evaluated as carriers in a liquid membrane transport system. A combination of ligand geometry and stereocontrolled substitution provides excellent Ag(+)-specific transport.