N-(thymin-1-ylacetyl)-N-(propyn-3-yl)glycine ethyl ester | 1349193-16-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(thymin-1-ylacetyl)-N-(propyn-3-yl)glycine ethyl ester
• 英文别名: Ethyl 2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-prop-2-ynylamino]acetate；ethyl 2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-prop-2-ynylamino]acetate
• CAS: 1349193-16-3
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: YXPSHSOLHFYRCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叠氮-三聚乙二醇-叔丁氧羰基 、 N-(thymin-1-ylacetyl)-N-(propyn-3-yl)glycine ethyl ester 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以76%的产率得到N-[N1-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-(thymin-1-ylacetyl)glycine ethyl ester
  参考文献：
  名称：

  Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs

  摘要：

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.124
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-N-(propyn-3-yl)glycine ethyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 N-(thymin-1-ylacetyl)-N-(propyn-3-yl)glycine ethyl ester
  参考文献：
  名称：

  Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs

  摘要：

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.124

文献信息

• Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs
  作者：Nicola M. Howarth、Jennyfer Ricci (née Goujon)

  DOI：10.1016/j.tet.2011.09.124

  日期：2011.12

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.