ethyl (Z)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate | 2924-80-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (Z)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate
• 英文别名: 2-trifluoroacetyl-3-ureido-acrylic acid ethyl ester；2-Trifluoracetyl-3-ureido-acrylsaeure-aethylester；ethyl (2Z)-2-[(carbamoylamino)methylidene]-4,4,4-trifluoro-3-oxobutanoate
• CAS: 2924-80-3
• 化学式: C₈H₉F₃N₂O₄
• 分子量: 254.166
• InChiKey: SOFQKYDFWCMSMI-ARJAWSKDSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethanol (64-17-5))
• 沸点：
  243.6±40.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.49
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate 以 氘代二甲亚砜 为溶剂， 生成 ethyl (E)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate
  参考文献：
  名称：

  Synthesis of pyrimidine derivatives based on ethyl 2-ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionates and urea

  摘要：

  在温和条件下，2-乙氧基亚甲基-3-聚氟烷基-3-氧代丙酸乙酯在乙氧基亚甲基取代基上与脲发生区域选择性缩合，生成 3-聚氟烷基-3-氧代-2-(脲亚甲基)丙酸乙酯。在更苛刻的条件下，后者会在氟酰基片段发生环化反应，生成 4-聚氟烷基-4-羟基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯。

  DOI：

  10.1007/s11172-009-0164-6
• 作为产物：
  描述：

  乙氧基-2-亚甲基三氟乙酰乙酸乙酯 、 尿素 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到ethyl (Z)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate
  参考文献：
  名称：

  Synthesis of pyrimidine derivatives based on ethyl 2-ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionates and urea

  摘要：

  在温和条件下，2-乙氧基亚甲基-3-聚氟烷基-3-氧代丙酸乙酯在乙氧基亚甲基取代基上与脲发生区域选择性缩合，生成 3-聚氟烷基-3-氧代-2-(脲亚甲基)丙酸乙酯。在更苛刻的条件下，后者会在氟酰基片段发生环化反应，生成 4-聚氟烷基-4-羟基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯。

  DOI：

  10.1007/s11172-009-0164-6

文献信息

• Source regions and timescales for the delivery of water to the Earth
  作者：A. Morbidelli、J. Chambers、J. I. Lunine、J. M. Petit、F. Robert、G. B. Valsecchi、K. E. Cyr

  DOI：10.1111/j.1945-5100.2000.tb01518.x

  日期：2000.11

  Abstract—In the primordial solar system, the most plausible sources of the water accreted by the Earth were in the outer asteroid belt, in the giant planet regions, and in the Kuiper Belt. We investigate the implications on the origin of Earth's water of dynamical models of primordial evolution of solar system bodies and check them with respect to chemical constraints. We find that it is plausible that the Earth accreted water all along its formation, from the early phases when the solar nebula was still present to the late stages of gas‐free sweepup of scattered planetesimals. Asteroids and the comets from the Jupiter‐Saturn region were the first water deliverers, when the Earth was less than half its present mass. The bulk of the water presently on Earth was carried by a few planetary embryos, originally formed in the outer asteroid belt and accreted by the Earth at the final stage of its formation. Finally, a late veneer, accounting for at most 10% of the present water mass, occurred due to comets from the Uranus‐Neptune region and from the Kuiper Belt. The net result of accretion from these several reservoirs is that the water on Earth had essentially the D/H ratio typical of the water condensed in the outer asteroid belt. This is in agreement with the observation that the D/H ratio in the oceans is very close to the mean value of the D/H ratio of the water inclusions in carbonaceous chondrites.
• Synthesis of pyrimidine derivatives based on ethyl 2-ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionates and urea
  作者：M. V. Goryaeva、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1007/s11172-009-0164-6

  日期：2009.6

  Ethyl 2-ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionates under mild conditions undergo regioselective condensation with urea at the ethoxymethylidene substituent giving rise to ethyl 3-polyfluoroalkyl-3-oxo-2-(ureidomethylidene)propionates. Under more drastic conditions, the latter cyclize at the fluoroacyl fragment to form ethyl 4-polyfluoroalkyl-4-hydroxy-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates.

  在温和条件下，2-乙氧基亚甲基-3-聚氟烷基-3-氧代丙酸乙酯在乙氧基亚甲基取代基上与脲发生区域选择性缩合，生成 3-聚氟烷基-3-氧代-2-(脲亚甲基)丙酸乙酯。在更苛刻的条件下，后者会在氟酰基片段发生环化反应，生成 4-聚氟烷基-4-羟基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯。