2-(3-phenylureido)malonic acid diethyl ester | 54001-50-2

• 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: 2-(3-phenylureido)malonic acid diethyl ester
• 英文别名: diethyl 2-(3-phenylureido)malonate；diethyl (N'-phenylureido)malonate；(N'-phenyl-ureido)-malonic acid diethyl ester；(N'-Phenyl-ureido)-malonsaeure-diaethylester；(ω-Phenyl-ureido)-malonsaeure-diaethylester；(N'-Phenylureido)-malonsaeure-diaethylester；Diethyl 2-(phenylcarbamoylamino)propanedioate
• CAS: 54001-50-2
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: NCEQMUTUWGKCFS-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  402.5±45.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-phenylureido)malonic acid diethyl ester 在 盐酸 作用下， 生成 3-苯基-2-氧代己内酰脲
  参考文献：
  名称：

  Gatewood, Journal of the American Chemical Society, 1925, vol. 47, p. 2178

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基丙二酸二乙酯 、 异氰酸苯酯 生成 2-(3-phenylureido)malonic acid diethyl ester
  参考文献：
  名称：

  Conversion of ureidomalonates and 5-carbalkoxyhydantoins to 5-ureido-4,6-pyrimidinediones

  摘要：

  DOI：

  10.1021/jo00828a062

文献信息

• Highly Stereoselective, One-Pot Synthesis of Azetidines and 2,4-Dioxo-1,3-diazabicyclo[3.2.0] Compounds Mediated by I₂
  作者：Chun-Bao Miao、Chun-Ping Dong、Min Zhang、Wen-Long Ren、Qi Meng、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1021/jo400181r

  日期：2013.5.3

  3-diazabicyclo[3.2.0] compounds with high stereoselectivities in a one-pot reaction mediated by I2. The tetramethylguanidine (TMG)/I2-mediated formal [2 + 2] cycloaddition reaction of α-amidomalonate 1 with enones 2 affords functionalized azetidine derivatives 4 in moderate to good yields with high diastereoselectivity. When the α-ureidomalonate 5 is used instead of 1, 2,4-dioxo-1,3-diazabicyclo[3.2.0]heptanes

  我们在这里报告一种方便的方法来构建由I 2介导的一锅反应中具有高立体选择性的多取代的氮杂环丁烷和2,4-二氧代-1,3-二氮杂双环[3.2.0]化合物。α-氨基天冬氨酸盐1与烯酮2的四甲基胍（TMG）/ I 2介导的正式[2 + 2]环加成反应以中等至良好的收率提供了高非对映选择性的官能化氮杂环丁烷衍生物4。当α-ureidomalonate 5代替1，2,4-二氧代-1,3-二氮杂双环[3.2.0]庚烷8和2,4-二氧代-1,3-二氮杂双环[3.2.0]庚烯9通过控制溶剂和温度可以选择性地制备。2,4-二氧代-1,3-二氮杂双环[3.2.0]庚烷8可以进一步经历与不同的亲核试剂，以得到相应的多官能化的氮杂环丁烷衍生物的开环反应13 - 16具有高steroselectivities。
• A Tunable Cascade Reaction of Ureidomalonates and Alkenyl Azlactones for the Divergent Synthesis of Hydantoins with Distinct Functional Groups
  作者：Lin Chen、Di Wang

  DOI：10.1021/acs.joc.3c02814

  日期：2024.3.1

  A tunable cascade reaction of ureidomalonates and alkenyl azlactones was disclosed, which gave rise to the construction of N-aroyl α-amino acid ester and imide-functionalized hydantoins in moderate to good yields and with excellent diastereoselectivities. The reaction pathway was precisely manipulated by organocatalysis and phase-transfer/sunlight relay catalysis, respectively, to realize the divergent

  公开了脲基丙二酸酯和烯基吖内酯的可调级联反应，该反应以中等至良好的收率和优异的非对映选择性构建了N-芳酰基α-氨基酸酯和酰亚胺官能化乙内酰脲。分别通过有机催化和相转移/阳光中继催化精确控制反应路径，实现发散合成。代表性产品的克级制备的成功展示了该方案的应用潜力。机理研究表明，乙氧基阴离子的交换和相转移在改变反应途径中起着关键作用，并且阳光可能会加速相转移催化引发的反应后期的氧化过程。
• Capuano,L. et al., Chemische Berichte, 1974, vol. 107, p. 3237 - 3245
  作者：Capuano,L. et al.

  DOI：——

  日期：——
• N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls
  作者：Sang-Hyeup Lee、Kazuhiro Yoshida、Hana Matsushita、Bruce Clapham、Guido Koch、Jürg Zimmermann、Kim D. Janda

  DOI：10.1021/jo048353u

  日期：2004.12.1

  Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.
• Khalafy, Jabbar; Prager, Rolf H.; Smith, Jason A., Journal of Chemical Research, Miniprint, 1999, # 2, p. 518 - 536
  作者：Khalafy, Jabbar、Prager, Rolf H.、Smith, Jason A.

  DOI：——

  日期：——