1-Piperidin-1-yl-2-(prop-2-ynylamino)ethanone | 1020932-16-4

• 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: 1-Piperidin-1-yl-2-(prop-2-ynylamino)ethanone
• CAS: 1020932-16-4
• 化学式: C₁₀H₁₆N₂O
• mdl: MFCD11149745
• 分子量: 180.25
• InChiKey: IAMUHULBGJYQKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Piperidin-1-yl-2-(prop-2-ynylamino)ethanone 在 copper(II) sulfate 、 三乙胺 、 维生素 C 作用下， 以 乙酸乙酯 、 乙腈 、 叔丁醇 为溶剂， 反应 29.0h， 生成 1-(cyclohexylmethyl)-3-methyl-4-((N-(2-oxo-2-(piperidin-1-yl)ethyl)acetamido)methyl)-1H-1,2,3-triazol-3-ium iodide
  参考文献：
  名称：

  The Click Triazolium Peptoid Side Chain: A Strongcis-Amide Inducer Enabling Chemical Diversity

  摘要：

  Access to homogeneous and discrete folded peptoid structures primarily depends on control of the cis/trans isomerism of backbone tertiary amides. This can be achieved by designing specific side chains capable of forming local interactions with the backbone. This is often undertaken at the expense of side-chain diversity, which is a key advantage of peptoids over other families of peptidomimetics. We report for the first time a positively charged triazolium-type side chain that does not compromise diversity and exhibits the best ability reported to date for inducing the cis conformation. The cis-directing effect was studied in N-acetamide dipeptoid model systems and evaluated in terms of K-cis/trans using NMR spectroscopy in aprotic and protic solvents. Computational geometry optimization and natural bond orbital analysis in combination with NOESY experiments were consistent with a model in which n -> pi*(Ar). electronic delocalization [from carbonyl (Oi-1) to the antibonding orbital (pi*) of the triazolium motif on residue i] may be operative. In the computational model (gas-phase) and experimentally in CDCl3, H-bonding between the triazolium C-H proton and the C-i=O-i, oxygen was also identified and may act cooperatively with the n -> pi*(Ar) delocalization, resulting in the absence of the trans rotamers in CDCl3.

  DOI：

  10.1021/ja302342h
• 作为产物：
  描述：

  哌啶 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-Piperidin-1-yl-2-(prop-2-ynylamino)ethanone
  参考文献：
  名称：

  The Click Triazolium Peptoid Side Chain: A Strongcis-Amide Inducer Enabling Chemical Diversity

  摘要：

  Access to homogeneous and discrete folded peptoid structures primarily depends on control of the cis/trans isomerism of backbone tertiary amides. This can be achieved by designing specific side chains capable of forming local interactions with the backbone. This is often undertaken at the expense of side-chain diversity, which is a key advantage of peptoids over other families of peptidomimetics. We report for the first time a positively charged triazolium-type side chain that does not compromise diversity and exhibits the best ability reported to date for inducing the cis conformation. The cis-directing effect was studied in N-acetamide dipeptoid model systems and evaluated in terms of K-cis/trans using NMR spectroscopy in aprotic and protic solvents. Computational geometry optimization and natural bond orbital analysis in combination with NOESY experiments were consistent with a model in which n -> pi*(Ar). electronic delocalization [from carbonyl (Oi-1) to the antibonding orbital (pi*) of the triazolium motif on residue i] may be operative. In the computational model (gas-phase) and experimentally in CDCl3, H-bonding between the triazolium C-H proton and the C-i=O-i, oxygen was also identified and may act cooperatively with the n -> pi*(Ar) delocalization, resulting in the absence of the trans rotamers in CDCl3.

  DOI：

  10.1021/ja302342h

文献信息

• The Click Triazolium Peptoid Side Chain: A Strong<i>cis</i>-Amide Inducer Enabling Chemical Diversity
  作者：Cécile Caumes、Olivier Roy、Sophie Faure、Claude Taillefumier

  DOI：10.1021/ja302342h

  日期：2012.6.13

  Access to homogeneous and discrete folded peptoid structures primarily depends on control of the cis/trans isomerism of backbone tertiary amides. This can be achieved by designing specific side chains capable of forming local interactions with the backbone. This is often undertaken at the expense of side-chain diversity, which is a key advantage of peptoids over other families of peptidomimetics. We report for the first time a positively charged triazolium-type side chain that does not compromise diversity and exhibits the best ability reported to date for inducing the cis conformation. The cis-directing effect was studied in N-acetamide dipeptoid model systems and evaluated in terms of K-cis/trans using NMR spectroscopy in aprotic and protic solvents. Computational geometry optimization and natural bond orbital analysis in combination with NOESY experiments were consistent with a model in which n -> pi*(Ar). electronic delocalization [from carbonyl (Oi-1) to the antibonding orbital (pi*) of the triazolium motif on residue i] may be operative. In the computational model (gas-phase) and experimentally in CDCl3, H-bonding between the triazolium C-H proton and the C-i=O-i, oxygen was also identified and may act cooperatively with the n -> pi*(Ar) delocalization, resulting in the absence of the trans rotamers in CDCl3.