肉桂酰甘氨酸甲酯 | 189618-39-1

• 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
• 中文名称: 肉桂酰甘氨酸甲酯
• 英文名称: Cinnamoylglycine methyl ester
• 英文别名: methyl 2-cinnamamidoacetate；cinnamoyl-glycine methyl ester；Cinnamoylglycine, methyl ester；methyl 2-[[(E)-3-phenylprop-2-enoyl]amino]acetate
• CAS: 189618-39-1
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD07352194
• 分子量: 219.24
• InChiKey: XFAGPDNLMRNSRO-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  肉桂酰甘氨酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (E)-cinnamoylglycine
  参考文献：
  名称：

  Artificial Trinuclear Metallopeptidase Synthesized by Cross-Linkage of a Molecular Bowl with a Polystyrene Derivative

  摘要：

  A novel methodology is reported for construction of active sites of artificial multinuclear metalloenzymes: transfer of metal-chelating sites confined in a prebuilt cage to a polymeric backbone. Artificial active sites comprising two or three moieties of Cu(II) complex of tris(2-aminoethyl)amine (tren) were prepared by transfer of Cu(II)tren units confined in a molecular bowl (MB) to poly(chloromethylstyrene-co-divinylbenzene) (PCD). By treatment of unreacted chloro groups of the resulting PCD with methoxide and destruction of the MB moieties attached to PCD with acid followed by addition of Cu(II) ion to the exposed tren moieties, catalytic polymers with peptidase activity were obtained. The average number (beta) of proximal Cu(II)tren moieties in the active site of the artificial multinuclear metallopeptidase was determined by quantifying the Cu(II) content. Several species of the artificial metallopeptidases with different beta contents were prepared and examined for catalytic activity in hydrolysis of various cinnamoyl amide derivatives. The PCD-based catalytic polymers did not hydrolyze a neutral amide but effectively hydrolyzed carboxyl-containing amides (N-cinnamoyl glycine, N-cinnamoyl beta-alanine, and N-cinnamoyl gamma-amino butyrate). Analysis of the kinetic data revealed that the active sites comprising three Cu(IT)tren units were mainly responsible for the catalytic activity. When analyzed in terms of k(cat), the catalytic activity of the PCD-based artificial peptidase was comparable to or better than the catalytic antibody with the highest peptidase activity reported to date. A mechanism is suggested for the effective cooperation among the three metal centers of the active site in hydrolysis of the carboxyl-containing amides.

  DOI：

  10.1021/ja000827t
• 作为产物：
  描述：

  methyl 2-[benzenesulfonyl-[(E)-3-phenylprop-2-enoyl]amino]acetate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以63%的产率得到肉桂酰甘氨酸甲酯
  参考文献：
  名称：

  Desulfonylation of Amides Using Samarium Iodide

  摘要：

  N-磺酰基酰胺的去磺酰化反应可通过在室温下与碘化镧(II) (SmI2)在THF中反应实现，产率从合理到优良均可。对带有芳基和烷基磺酰基的非环状和环状酰胺的去保护也是可行的。

  DOI：

  10.1055/s-1997-771

文献信息

• Efficient and Flexible Synthesis of Highly Functionalised 4‐Aminooxazoles by a Gold‐Catalysed Intermolecular Formal [3+2] Dipolar Cycloaddition
  作者：Andrew D. Gillie、Raju Jannapu Reddy、Paul W. Davies

  DOI：10.1002/adsc.201500905

  日期：2016.1.21

  fully substituted and functionalised 4‐aminooxazoles are accessed by an efficient intermolecular reaction between an ynamide and an N‐acylpyridinium N‐aminide in the presence of a gold catalyst. The formal [3+2] dipolar cycloaddition employs a nucleophilic nitrenoid approach to access the 1,3‐N,O‐dipole character in a controllable fashion. The selectivity for a cycloaddition pathway provides a stark

  恶唑是生物活性和功能性材料中的重要基序。在金催化剂的存在下，通过酰胺与N-酰基吡啶鎓N-氨基化物之间的有效分子间反应，可以得到复杂的，完全取代且官能化的4-氨基恶唑。正式的[3 + 2]偶极环加成反应采用亲核亚硝酰方法来接近1,3- N，O可控偶极子角色。环加成途径的选择性与亲电酰基腈的不分皂白的反应性形成了鲜明的对比。据报道，从可利用的前体包括羧酸酯和酸形成酰基官能化胺的方法。研究了这些胺类在恶唑形成反应中的功能，结果表明尽管靠近反应中心，仍可进行大量精制。因此，可以容易地获得基于功能性恶唑的基序，例如具有生物学相关取代模式的手性恶唑。已经评估了在金催化中未探索或很少使用的乙酰胺类型的使用。恶唑周围异常的全杂原子取代模式已显示可使用硫代乙酰胺实现。研究表明，在实际上简单的多毫摩尔规模的反应中，与理想的化学计量接近的反应物以及相对较低的稳定型前催化剂负载量是合适的。这种区域选择性分子间制剂
• Cinnamic acid derivatives, photocrosslinkable cinnamic acid-polymer derivative and crosslinked cinnamic acid polymer derivatives
  申请人：SEIKAGAKU KOGYO KABUSHIKI KAISHA (SEIKAGAKU CORPORATION)

  公开号：EP0713859A2

  公开（公告）日：1996-05-29

  The invention provides a cinnamic acid derivative having a novel spacer introduced into cinnamic acid which is photodimerizable, a cinnamic acid-polymer derivative photocurable with high sensitivity and efficiency obtainable by introducing the above cinnamic acid derivative into a host polymer such as a glycosaminoglycan, and a photocrosslinked cinnamic acid-polymer derivative obtainable by exposing the same cinnamic aicd-polymer derivative to ultraviolet light irradiation.

  本发明提供了一种肉桂酸衍生物，它在肉桂酸中引入了可进行光二聚化的新型间隔物；一种肉桂酸-聚合物衍生物，通过将上述肉桂酸衍生物引入主聚合物（如糖胺聚糖）中，可获得高灵敏度和高效率的光固化肉桂酸-聚合物衍生物；以及一种光交联肉桂酸-聚合物衍生物，通过将相同的肉桂酸-聚合物衍生物暴露于紫外线照射下，可获得光交联肉桂酸-聚合物衍生物。
• FIEZ-VANDAL, PIERRE-YVES
  作者：FIEZ-VANDAL, PIERRE-YVES

  DOI：——

  日期：——
• US5212158A
  申请人：——

  公开号：US5212158A

  公开（公告）日：1993-05-18
• US6025444A
  申请人：——

  公开号：US6025444A

  公开（公告）日：2000-02-15