[2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester | 1089216-03-4

• 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-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[2-(butylcarbamoylamino)-7-(cyclohexylmethyl)-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]acetate
• CAS: 1089216-03-4
• 化学式: C₂₂H₃₃N₅O₄
• 分子量: 431.535
• InChiKey: VWWLNHFKTGAZEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以98%的产率得到[2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid
  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
• 作为产物：
  描述：

  (2-amino-7-cyclohexylmethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)-acetic acid ethyl ester 、 异氰酸正丁酯 在 吡啶 作用下， 反应 16.0h， 以65%的产率得到[2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester
  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.