(Z)-3-benzoylamino-acrylic acid ethyl ester | 869902-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-benzoylamino-acrylic acid ethyl ester
• 英文别名: N-[ethoxy (Z)-propenoyl]benzamide；(Z)-ethyl 3-(benzamido)acrylate；ethyl N-benzoylaminoacrylate；ethyl (Z)-3-benzamidoacrylate；ethyl (Z)-3-benzamidoprop-2-enoate
• CAS: 869902-41-0
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: UUFLONADCIJUJL-HJWRWDBZSA-N

物化性质

• 沸点：
  392.6±34.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (Z)-3-benzoylamino-acrylic acid ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以90%的产率得到N-[(1E)-2-carbamoylvinyl]benzamide
  参考文献：
  名称：

  New [11C]Phosgene Based Synthesis of [11C]Pyrimidines for Positron Emission Tomography

  摘要：

  Thymine, 5-FU, and uracil were successfully synthesized through a procedure involving a cyclocondensation of triphosgene with newly developed alpha-substituted beta-aminoacrylamides intermediates (1a, X = Me; 1b, X = F; 1c, X = H). The radioligands [2-C-11]thymine and [2-C-11]5-fluorouracil were synthesized in high radiochemical yields in 16-17 minutes from the end of bombardment by applying the cyclocondensation method with [C-11]COCl2,

  DOI：

  10.3987/com-08-s(f)116
• 作为产物：
  描述：

  (E)-3-benzoylamino-acrylic acid ethyl ester 以 乙腈 为溶剂， 反应 4.0h， 以30%的产率得到(Z)-3-benzoylamino-acrylic acid ethyl ester
  参考文献：
  名称：

  New [11C]Phosgene Based Synthesis of [11C]Pyrimidines for Positron Emission Tomography

  摘要：

  Thymine, 5-FU, and uracil were successfully synthesized through a procedure involving a cyclocondensation of triphosgene with newly developed alpha-substituted beta-aminoacrylamides intermediates (1a, X = Me; 1b, X = F; 1c, X = H). The radioligands [2-C-11]thymine and [2-C-11]5-fluorouracil were synthesized in high radiochemical yields in 16-17 minutes from the end of bombardment by applying the cyclocondensation method with [C-11]COCl2,

  DOI：

  10.3987/com-08-s(f)116

文献信息

• Hydrogen-Bond-Directed Highly Stereoselective Synthesis of Z-Enamides via Pd-Catalyzed Oxidative Amidation of Conjugated Olefins
  作者：Ji Min Lee、Doo-Sik Ahn、Doo Young Jung、Junseung Lee、Youngkyu Do、Sang Kyu Kim、Sukbok Chang

  DOI：10.1021/ja0639315

  日期：2006.10.1

  amidation reaction has a broad substrate scope, allowing alkyl, aryl, and vinyl amides to react with olefins conjugated with ester, amide, phosphonate, and ketone groups. The notable preference for the formation of Z-enamides is presumably due to the presence of an intramolecular hydrogen bond between the amido proton and the carbonyl oxygen. The energy difference between two plausible sigma-alkylamidopalladium

  已经开发了一种制备 Z-烯酰胺的有效方法，包括使用 Pd/Cu 助催化剂体系使伯酰胺与共轭烯烃反应。发现某些添加剂，如氧化膦和膦酸盐，在氧气氛下提高了非极性溶剂中的反应效率，从而在瓦克型条件下以高产率生产各种 Z-烯酰胺，具有优异的立体选择性。氧化酰胺化反应具有广泛的底物范围，允许烷基、芳基和乙烯基酰胺与与酯、酰胺、膦酸酯和酮基团共轭的烯烃反应。形成 Z-烯酰胺的显着偏好可能是由于酰氨基质子和羰基氧之间存在分子内氢键。两种可能的 σ-烷基酰胺钯中间体之间的能量差异分别导致 Z-和 E-异构烯酰胺产物，计算为 4.18 kcal/mol。β-氢化物消除步骤被认为是整个氧化酰胺化过程中的立体化学决定步骤，导致Z-烯酰胺的过渡态的能级比导致E-异构体的能级低5.35 kcal/mol . 观察到 Z-和 E-烯酰胺之间的光异构化效率在很大程度上取决于底物的取代基，并且某些 E-烯酰胺可以通过 Z
• Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
  作者：Lili Chen、Xiaoliang Zou、Haonan Zhao、Senmiao Xu

  DOI：10.1021/acs.orglett.7b01740

  日期：2017.7.7

  delivering a series of stable functionalized chiral α-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral α-amino boronate esters.

  首次开发了使用双（频哪醇）二硼的铜催化Z -β-酰胺基丙烯腈和E -β-酰胺基丙烯酸乙酯的不对称原硼酸酯。该方法可耐受各种各样的底物，在温和的反应条件下，可以以良好的收率和对映选择性提供一系列稳定的官能化手性α-氨基硼酸酯。当前的方法也适用于克级合成，而不会削弱对映选择性。这项工作提供了一种有吸引力的和互补的方法来合成对映体的手性α-氨基硼酸酯。
• An Efficient Approach to the Stereocontrolled Synthesis of Enamides
  作者：Mathew V. J. Villa、Sarah M. Targett、John C. Barnes、William G. Whittingham、Rodolfo Marquez

  DOI：10.1021/ol070336e

  日期：2007.4.1

  [reaction: see text] A fast, flexible, and efficient approach for the stereocontrolled synthesis of enamides has been developed starting from lactams and amides through the use of imides. This new approach provides access to enamide systems not easily or currently accessible through other approaches.

  [反应：见正文]已经从内酰胺和酰胺开始，通过使用酰亚胺，开发了一种快速，灵活和有效的方法，用于立体控制合成酰胺。这种新方法提供了对不容易或目前无法通过其他方法访问的酰胺系统的访问。
• Copper-Catalyzed Enantioselective Synthesis of β-Boron β-Amino Esters
  作者：Aurora López、Timothy B. Clark、Alejandro Parra、Mariola Tortosa

  DOI：10.1021/acs.orglett.7b02784

  日期：2017.12.1

  In this report, the enantioselective, copper-catalyzed borylation of β-amidoacrylates is disclosed. A broad variety of biologically important α-aminoboronates has been prepared with consistently high levels of enantiocontrol using an inexpensive copper catalyst and a commercially available chiral ligand. The method can be applied to the synthesis of novel boron-containing dipeptides and hemiboronates

  在该报告中，公开了β-酰胺基丙烯酸酯的对映选择性的铜催化的硼酸酯化。已经使用廉价的铜催化剂和可商购的手性配体制备了具有一致高水平对映体控制的多种生物学上重要的生物学重要的α-氨基硼酸酯。该方法可用于合成新型的含硼二肽和半硼酸酯。
• Magnetically recyclable palladium nanoparticles (Fe ₃ O ₄ ‐Pd) for oxidative coupling between amides and olefins at room temperature
  作者：Chandan Kumar Pal、Swagatika Sahu、Ranjan Kumar Sahu、Rajesh Kumar Singh、Ashis Kumar Jena

  DOI：10.1002/aoc.4985

  日期：2019.8

  for the synthesis of magnetically recyclable palladium nanoparticles (Fe3O4‐Pd) is described. The catalytic application of the Fe3O4‐Pd nanoparticles was explored for the first time in oxidative coupling between amides and olefins. p‐Toluenesulfonic acid plays a significant role in the oxidative amidation reaction. The reaction proceeds at room temperature, resulting in (Z)‐enamides under ambient air

  描述了一种方便的合成可磁回收钯纳米颗粒（Fe 3 O 4 -Pd）的方法。Fe 3 O 4 -Pd纳米颗粒的催化应用首次在酰胺和烯烃之间的氧化偶联中得到了探索。对甲苯磺酸在氧化酰胺化反应中起着重要作用。反应在室温下进行，在没有助催化剂和配体的情况下，在环境空气中生成（Z）酰胺。Fe 3 O 4的超顺磁性‐Pd有助于轻松，定量地从反应混合物中回收催化剂，并且可以重复使用多达三个连续周期，但催化活性会略有下降。