2-ethynylindole-1-carboxylic acid tert-butyl ester | 680210-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-ethynylindole-1-carboxylic acid tert-butyl ester
• 英文别名: (1-tert-butoxycarbonyl-2-ethynyl)-indole；tert-butyl2-ethynyl-1H-indole-1-carboxylate；tert-butyl 2-ethynylindole-1-carboxylate
• CAS: 680210-66-6
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: MLGSLRLREFBJPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethynylindole-1-carboxylic acid tert-butyl ester 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium methylate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.17h， 生成 2,7-bis-(1H-indole-2-yl)ethynyl-1,8-naphthyridine
  参考文献：
  名称：

  Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors:  Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine

  摘要：

  The push-pull conjugated molecules 2,7-bis-(1 H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN) and 2,7-bis(1H-indol-2-yl)ethynyl-1,8-naphthyridine (BIN) adopting daad relays of proton donors (d) and acceptors (a) form multiple hydrogen-bonding complexes with various monosaccharides that possess complementary adda sequences. Although the free BPN emits blue light at lambda(max) = 475 nm in CH2CI2, its complexation with octyl ss-D-glucopyranoside gives green fluorescence at lambda(max) = 535 nm. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM. On the other hand, the CD-silent BIN molecule binds with monosaccharides to form the CD-active multiple hydrogen-bonding complexes, which exhibit the remarkable chirality dependent helicities consistent with the prediction by the ab initio approaches. On the basis of the similar daad cleft and hence the binding property, the fluorescence and CD absorption methods in BPN and BIN, respectively, are complementary, which, in combination with computational molecular modeling, not only give a detailed insight into the structures of the receptor-saccharide complexes in solution, but also differentiate octyl beta-D-glucopyranoside from its enantiomer and other monosaccharides.

  DOI：

  10.1021/ja039237w
• 作为产物：
  描述：

  2-碘-N-(叔-丁氧羰基)吲哚 在 bis-triphenylphosphine-palladium(II) chloride 甲醇 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.2h， 生成 2-ethynylindole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors:  Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine

  摘要：

  The push-pull conjugated molecules 2,7-bis-(1 H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN) and 2,7-bis(1H-indol-2-yl)ethynyl-1,8-naphthyridine (BIN) adopting daad relays of proton donors (d) and acceptors (a) form multiple hydrogen-bonding complexes with various monosaccharides that possess complementary adda sequences. Although the free BPN emits blue light at lambda(max) = 475 nm in CH2CI2, its complexation with octyl ss-D-glucopyranoside gives green fluorescence at lambda(max) = 535 nm. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM. On the other hand, the CD-silent BIN molecule binds with monosaccharides to form the CD-active multiple hydrogen-bonding complexes, which exhibit the remarkable chirality dependent helicities consistent with the prediction by the ab initio approaches. On the basis of the similar daad cleft and hence the binding property, the fluorescence and CD absorption methods in BPN and BIN, respectively, are complementary, which, in combination with computational molecular modeling, not only give a detailed insight into the structures of the receptor-saccharide complexes in solution, but also differentiate octyl beta-D-glucopyranoside from its enantiomer and other monosaccharides.

  DOI：

  10.1021/ja039237w

文献信息

• Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors:  Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine
  作者：Jim-Min Fang、Srinivasan Selvi、Jen-Hai Liao、Zdenek Slanina、Chao-Tsen Chen、Pi-Tai Chou

  DOI：10.1021/ja039237w

  日期：2004.3.1

  The push-pull conjugated molecules 2,7-bis-(1 H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN) and 2,7-bis(1H-indol-2-yl)ethynyl-1,8-naphthyridine (BIN) adopting daad relays of proton donors (d) and acceptors (a) form multiple hydrogen-bonding complexes with various monosaccharides that possess complementary adda sequences. Although the free BPN emits blue light at lambda(max) = 475 nm in CH2CI2, its complexation with octyl ss-D-glucopyranoside gives green fluorescence at lambda(max) = 535 nm. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM. On the other hand, the CD-silent BIN molecule binds with monosaccharides to form the CD-active multiple hydrogen-bonding complexes, which exhibit the remarkable chirality dependent helicities consistent with the prediction by the ab initio approaches. On the basis of the similar daad cleft and hence the binding property, the fluorescence and CD absorption methods in BPN and BIN, respectively, are complementary, which, in combination with computational molecular modeling, not only give a detailed insight into the structures of the receptor-saccharide complexes in solution, but also differentiate octyl beta-D-glucopyranoside from its enantiomer and other monosaccharides.