2-hydroxyethyl-2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetate | 1089216-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-hydroxyethyl-2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetate
• 英文别名: 2-hydroxyethyl 2-[2-(butylcarbamoylamino)-7-(cyclohexylmethyl)-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]acetate
• CAS: 1089216-09-0
• 化学式: C₂₂H₃₃N₅O₅
• 分子量: 447.535
• InChiKey: ANTWQNWMAQWEIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl-2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetate 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 2-(2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetoxy)ethyl (2-(methacryloyloxy)ethyl) succinate
  参考文献：
  名称：

  Synthesis of a Redox-Responsive Quadruple Hydrogen-Bonding Unit for Applications in Supramolecular Chemistry

  摘要：

  A redox-responsive quadruple hydrogen-bonding module (eDAN) has been developed. The strong binding between the reduced form and its partner (DeUG) can be significantly decreased upon oxidation but restored upon subsequent reduction. This on-off switch was successfully applied to provide reversible control of macroscopic supramolecular polymer networks.

  DOI：

  10.1021/ja2069278
• 作为产物：
  描述：

  [2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester 、 乙二醇 在 potassium cyanide 作用下， 反应 16.0h， 以87%的产率得到2-hydroxyethyl-2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetate
  参考文献：
  名称：

  Hydrogen-Bonded DeUG·DAN Heterocomplex: Structure and Stability and a Scalable Synthesis of DeUG with Reactive Functionality

  摘要：

  A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K-assoc for the 1.2 heterocomplex was estimated to be 2 x 10(8) M-1 in chloroform.

  DOI：

  10.1021/ol802344w

文献信息

• Hydrogen-Bonded DeUG·DAN Heterocomplex: Structure and Stability and a Scalable Synthesis of DeUG with Reactive Functionality
  作者：Darrell W. Kuykendall、Cyrus A. Anderson、Steven C. Zimmerman

  DOI：10.1021/ol802344w

  日期：2009.1.1

  A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K-assoc for the 1.2 heterocomplex was estimated to be 2 x 10(8) M-1 in chloroform.
• Synthesis of a Redox-Responsive Quadruple Hydrogen-Bonding Unit for Applications in Supramolecular Chemistry
  作者：Ying Li、Taiho Park、J. Kwansima Quansah、Steven C. Zimmerman

  DOI：10.1021/ja2069278

  日期：2011.11.2

  A redox-responsive quadruple hydrogen-bonding module (eDAN) has been developed. The strong binding between the reduced form and its partner (DeUG) can be significantly decreased upon oxidation but restored upon subsequent reduction. This on-off switch was successfully applied to provide reversible control of macroscopic supramolecular polymer networks.