ethyl 2-azido-3-phenylacrylate | 61013-61-4

• 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: ethyl 2-azido-3-phenylacrylate
• 英文别名: (E/Z)-ethyl 2-azido-3-phenylacrylate；3-phenyl-2-azido ethyl acrylate；Ethyl 2-azido-3-phenylprop-2-enoate；ethyl 2-azido-3-phenylprop-2-enoate
• CAS: 61013-61-4
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: YKMYSYKQMDHFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  ethyl 2-azido-3-phenylacrylate 在 氯化锆(IV) 、 silver nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以70%的产率得到吲哚-2-羧酸乙酯
  参考文献：
  名称：

  ZrCl₄-promoted facile synthesis of indole derivatives

  摘要：

  锆（IV）氯化物有效地激活芳基叠氮丙烯酸酯中的氮（N2）挤出，随后进行环化反应，以中等至良好的产率提供所需的吲哚产物。

  DOI：

  10.1039/c4ra02158d
• 作为产物：
  描述：

  ethyl 3-acetyloxy-2-azido-3-phenylpropanoate 在 sodium azide 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 ethyl 2-azido-3-phenylacrylate
  参考文献：
  名称：

  NOVEL SYNTHESIS OF THE TAUTOMERIC ISOMER OF THE AZIRINOMYCIN ETHYL ESTER AND ITS ANALOGUES

  摘要：

  已成功合成了乙基2-叠氮基-2-烯酸酯（4）和乙基3-叠氮基-2-烯酸酯（5），并通过光解或热裂解将4和5转化为2-烷基-3-乙oxycarbonyl-2H-氮杂环烯和3-烷基-2-乙oxycarbonyl-2H-氮杂环烯。

  DOI：

  10.1246/cl.1976.1063

文献信息

• Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide
  作者：Wenteng Chen、Jiaan Shao、Zhi Li、Marc A. Giulianotti、Yongping Yu

  DOI：10.1139/v11-150

  日期：2012.2

  A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

  从对甲苯甲基异氰酸酯（TOSMIC）和容易合成的乙烯基叠氮化合物中合成多取代吡咯的简便方法已经开发出来。在碱的存在下，在温和条件下进行反应。2-对甲苯基取代的吡咯以中等至良好的收率得到。此外，还开发了一种碱引发的一锅法吡咯合成方法，使用羧醛、乙酸叠氮乙酯和TOSMIC。
• Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds
  作者：Eileen Pei Jian Ng、Yi-Feng Wang、Benjamin Wei-Qiang Hui、Guillaume Lapointe、Shunsuke Chiba

  DOI：10.1016/j.tet.2011.08.006

  日期：2011.10

  Tri- and tetrasubstituted N–H pyrroles were prepared by the simple treatment of vinyl azides with 1,3-dicarbonyl compounds in toluene at 100 °C via 2H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1,3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K2CO3, 1-vinyl-1,2,3-triazoles were obtained via 1,3-dipolar cycloaddition. These

  三-和四取代Ñ经由2在100℃下在甲苯中的简单处理乙烯基叠氮化物与1,3-二羰基化合物制备-H吡咯ħ原位产生-azirine中间体。当在催化量的K 2 CO 3存在下，叠氮化乙烯和1,3-二羰基化合物的反应在DMF中进行时，通过1,3-偶极环加成反应获得1-乙烯基-1,2,3-三唑。这些方法利用了叠氮化乙烯基化学反应的正交模式，这可以通过稍微改变反应条件来实现。
• New Findings on the Hemetsberger-Knittel Reaction (Synthetic Studies on Indoles and Related Compounds. XLIII.
  作者：Yasuoki MURAKAMI、Toshiko WATANABE、Hideharu SUZUKI、Nobuyo KOTAKE、Tomoko TAKAHASHI、Kiyono TOYONARI、Masami OHNO、Kyoko TAKASE、Takayuki SUZUKI、Kazuhiro KONDO

  DOI：10.1248/cpb.45.1739

  日期：——

  In the Hemetsberger-Knittel reaction for indole synthesis, the intermediate ethyl 2-azido-3-hydroxy-3-aryl-propionate (4) was found to be formed in the reaction of arylaldehyde 1 with ethyl azidoacetate at a lower temperature (-30°C) as the main product, while only ethyl 2-azidocinnamate (2) is known to be formed at a higher temperature (0°C). It was also found that fluoride ion was effective for obtaining 4. Compound 4 was converted to 2 in good yield by treatment with SOCl2/pyridine or SOCl2/Et3N. A trial application of this reaction to ketone is also described.

  在合成吲哚的海梅茨贝格-克尼特尔反应中，发现当芳香醛1与叠氮乙酸乙酯在较低温度（-30°C）下反应时，主要生成中间体乙基2-叠氮-3-羟基-3-芳基丙酸酯（4），而在较高温度（0°C）下仅知生成乙基2-叠氮肉桂酸酯（2）。研究发现，氟离子对此生成4有效。通过使用SOCl2/吡啶或SOCl2/Et3N处理，4能良好地转化为2。此外，还描述了将该反应尝试应用于酮类的情况。
• Chemoselective reduction of azides catalyzed by molybdenum xanthate by using phenylsilane as the hydride source
  作者：Mahagundappa R. Maddani、Saravana K. Moorthy、Kandikere R. Prabhu

  DOI：10.1016/j.tet.2009.10.093

  日期：2010.1

  A chemoselective, neutral, and efficient strategy for the reduction of azides to corresponding amines catalyzed by dioxobis(N,N,-diethyldithiocarbamato) molybdenum complex (1, MoO2[S2CNEt2]2) in the presence of phenylsilane is discovered. This chemoselective reduction strategy tolerates a variety of reducible functional groups.

  发现了在苯基硅烷存在下，由二氧双（N，N，-diethyldithiocarbamato ）钼配合物（1，MoO 2 [S 2 CNEt 2 ] 2）催化的将叠氮化物还原为相应胺的化学选择，中性和有效策略。这种化学选择性还原策略可耐受多种可还原的官能团。
• Synthesis of Substituted Indoles from 2-Azidoacrylates and <i>ortho</i>-Silyl Aryltriflates
  作者：Deng Hong、Zhengbo Chen、Xufeng Lin、Yanguang Wang

  DOI：10.1021/ol101934v

  日期：2010.10.15

  2-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.

  2-叠氮基丙烯酸酯在PPh 3和CsF的存在下与苯炔反应，以高收率提供取代的吲哚。该反应涉及亚氨基磷烷和苯炔的形成以及随后的双环化/水解/空气氧化级联反应。该方法用于合成10 H-吲哚并[1,2-a]吲哚-10-酮。