(Z)-methyl 2-azido-3-phenylacrylate | 81777-11-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-azido-3-phenylacrylate
• 英文别名: methyl (Z)-2-azido-3-phenylacrylate；methyl 2-azido-3-phenylacrylate；methyl (Z)-2-azido-3-phenylprop-2-enoate
• CAS: 81777-11-9
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: HZPRAUOGOBIGGF-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-azido-3-phenylacrylate 在 Rh₄(3,3'-[1,3-phenylenebis(ethyne-2,1-diyl)]dibenzoicacid(-H))₄(H₂O)₂(dimethylacetamide)₂ 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以94%的产率得到吲哚-2-羧酸甲酯
  参考文献：
  名称：

  A porous metal–organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis

  摘要：

  一种具有Rh-Rh键的多孔金属-有机笼（MOC-Rh-1）已经制备完成，可作为异质催化剂，并促进偶氮化物的分子内C-H胺化反应。

  DOI：

  10.1039/c5ta05592j
• 作为产物：
  描述：

  methyl erythro-3-azido-2-iodo-3-phenylpropanoate 在 碘叠氮化物 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (Z)-methyl 2-azido-3-phenylacrylate
  参考文献：
  名称：

  Cambie, Richard C.; Jurlina, Jeffrey L.; Rutledge, Peter S., Journal of the Chemical Society. Perkin transactions I, 1982, p. 327 - 334

  摘要：

  DOI：

文献信息

• A Fast Procedure for the Preparation of Amides/Peptides from Carboxylic Acids and Azides via Two Redox Reactions: Application to the Synthesis of Methionine Enkephalin
  作者：Sunil K. Ghosh、Rekha Verma、Usha Ghosh、Vasant R. Mamdapur

  DOI：10.1246/bcsj.69.1705

  日期：1996.6

  A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction–oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid derivatives respectively as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has

  已经描述了基于两个还原-氧化（氧化还原）反应的用于合成酰胺/肽的一锅自调节方法。一级和二级酰胺/肽分别使用叠氮三甲基硅烷和烷基叠氮化物/α-叠氮酸衍生物作为胺组分的直接来源制备。已发现在羧基活化过程中在反应介质中产生的苯甲酚是用于将叠氮化物转化为伯胺的有效还原剂。该方法已应用于甲硫氨酸脑啡肽的合成。
• Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates
  作者：Alexander G. O'Brien、François Lévesque、Peter H. Seeberger

  DOI：10.1039/c0cc04481d

  日期：——

  An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

  已经开发了一种有效，安全和可扩展的方法，用于叠氮丙烯酸酯的连续流热解以生成吲哚，并将其用于相关杂环的合成。该方法的可扩展性在DAAO抑制剂4H-呋喃[3,2-b]吡咯-5-羧酸的前体的连续流动合成中得到证明。
• A porous metal–organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis
  作者：Lianfen Chen、Tao Yang、Hao Cui、Tao Cai、Li Zhang、Cheng-Yong Su

  DOI：10.1039/c5ta05592j

  日期：——

  A porous metal–organic cage (MOC-Rh-1) with Rh–Rh bonds has been prepared, which can act as a heterogeneous catalyst and promote the intramolecular C–H amination of azides.

  一种具有Rh-Rh键的多孔金属-有机笼（MOC-Rh-1）已经制备完成，可作为异质催化剂，并促进偶氮化物的分子内C-H胺化反应。
• Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C−H Amination
  作者：Julien Bonnamour、Carsten Bolm

  DOI：10.1021/ol2004066

  日期：2011.4.15

  A practical iron-catalyzed intramolecular C−H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.

  提出了一种实用的铁催化分子内胺化反应及其在吲哚衍生物合成中的应用。作为催化剂，使用可商购的三氟甲磺酸铁（II）。
• Derivatives of Azidocinnamic Acid in the Synthesis of 2-Amino-4-Arylidene-1H-Imidazol-5(4H)-Ones
  作者：Alexander Yu. Smirnov、Nadezhda S. Baleeva、Snezhana O. Zaitseva、Konstantin S. Mineev、Mikhail S. Baranov

  DOI：10.1007/s10593-018-2318-7

  日期：2018.6

  A method for the synthesis of 2-amino-4-arylidene-1H-imidazol-5(4H)-ones is proposed based on the reaction of various aromatic isocyanates with phosphazenes derived from azidocinnamic acid amides. The spectral-luminescent properties of the obtained compounds were studied. The products were shown to possess the (Z)-configuration with the help of two-dimensional spectroscopy.

  基于各种芳族异氰酸酯与衍生自叠氮基叠氮化酰胺的磷腈的反应，提出了一种2-氨基-4-亚芳基-1 H-咪唑-5（4 H）-ones的合成方法。研究了所得化合物的光谱发光性质。在二维光谱学的帮助下，显示出产物具有（Z）构型。