diethyl (E)-4-oxo-2-heptendioate | 59742-69-7

• 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: diethyl (E)-4-oxo-2-heptendioate
• 英文别名: 4-oxo-hept-2t-enedioic acid diethyl ester；4-Oxo-hept-2t-endisaeure-diaethylester；(2E)-4-Oxoheptenedioate；diethyl (E)-4-oxohept-2-enedioate
• CAS: 59742-69-7
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: YSXDKKYVUOEOGS-FNORWQNLSA-N

物化性质

• 沸点：
  337.6±27.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (E)-4-oxo-2-heptendioate 在 水 作用下， 生成
  参考文献：
  名称：

  4-氧-庚二酸类似物对二氢二吡啶甲酸酯合酶的不可逆抑制作用。

  摘要：

  我们报告了（2E，5E）-4-氧庚二烯二酸和（2E）-4-氧庚二烯酸的合成以及作为细菌二氢二吡啶甲酸酯合酶抑制剂的二酯和二酸类似物的评价。酶动力学研究可以确定失活的二级速率常数。底物共孵育研究表明，抑制剂在活性位点起作用。质谱分析进一步探索了酶-抑制剂的相互作用并确定了酶烷基化的位点。

  DOI：

  10.1016/j.bmc.2008.10.026
• 作为产物：
  描述：

  4-氧代庚二酸二乙酯 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 diethyl (E)-4-oxo-2-heptendioate
  参考文献：
  名称：

  Two new irreversible inhibitors of dihydrodipicolinate synthase: diethyl (E,E)-4-oxo-2,5-heptadienedioate and diethyl (E)-4-oxo-2-heptenedioate

  摘要：

  Dihydrodipicolinate synthase (DHDPS) is a key enzyme in lysine biosynthesis and an important antibiotic target. The enzyme catalyses the condensation of (S)-aspartate semialdehyde (ASA) and pyruvate to form dihydrodipicolinate. Two new irreversible inhibitors of dihydrodipicolinate synthase are reported, designed to mimic the acyclic enzyme-bound condensation product of ASA and pyruvate. These compounds represent an important new lead in the design of potent inhibitors for this enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.043

文献信息

• Using High Hydraulic Conductivity Nodes to Simulate Seepage Lakes
  作者：Mary P. Anderson、Randall J. Hunt、James T. Krohelski、Kuopo Chung

  DOI：10.1111/j.1745-6584.2002.tb02496.x

  日期：2002.3

  AbstractIn a typical ground water flow model, lakes are represented by specified head nodes requiring that lake levels be known a priori. To remove this limitation, previous researchers assigned high hydraulic conductivity (K) values to nodes that represent a lake, under the assumption that the simulated head at the nodes in the high‐K zone accurately reflects lake level. The solution should also produce a constant water level across the lake. We developed a model of a simple hypothetical ground water/lake system to test whether solutions using high‐K lake nodes are sensitive to the value of K selected to represent the lake. Results show that the larger the contrast between the K of the aquifer and the K of the lake nodes, the smaller the error tolerance required for the solution to converge. For our test problem, a contrast of three orders of magnitude produced a head difference across the lake of 0.005 m under a regional gradient of the order of 10−3 m/m, while a contrast of four orders of magnitude produced a head difference of 0.001 m. The high‐K method was then used to simulate lake levels in Pretty Lake, Wisconsin. Results for both the hypothetical system and the application to Pretty Lake compared favorably with results using a lake package developed for MODFLOW (Merritt and Konikow 2000). While our results demonstrate that the high‐K method accurately simulates lake levels, this method has more cumbersome postprocessing and longer run times than the same problem simulated using the lake package.
• Irreversible inhibition of dihydrodipicolinate synthase by 4-oxo-heptenedioic acid analogues
  作者：Berin A. Boughton、Michael D.W. Griffin、Paul A. O’Donnell、Renwick C.J. Dobson、Matthew A. Perugini、Juliet A. Gerrard、Craig A. Hutton

  DOI：10.1016/j.bmc.2008.10.026

  日期：2008.12

  We report the synthesis of (2E,5E)-4-oxoheptadienedioic acid and (2E)-4-oxoheptenedioic acid and evaluation of both diester and diacid analogues as inhibitors of bacterial dihydrodipicolinate synthase. Enzyme kinetic studies allowed the determination of second-order rate constants of inactivation; and substrate co-incubation studies have shown the inhibitors act at the active-site. Mass spectrometric

  我们报告了（2E，5E）-4-氧庚二烯二酸和（2E）-4-氧庚二烯酸的合成以及作为细菌二氢二吡啶甲酸酯合酶抑制剂的二酯和二酸类似物的评价。酶动力学研究可以确定失活的二级速率常数。底物共孵育研究表明，抑制剂在活性位点起作用。质谱分析进一步探索了酶-抑制剂的相互作用并确定了酶烷基化的位点。
• Two new irreversible inhibitors of dihydrodipicolinate synthase: diethyl (E,E)-4-oxo-2,5-heptadienedioate and diethyl (E)-4-oxo-2-heptenedioate
  作者：Jennifer J. Turner、Jackie P. Healy、Renwick C.J. Dobson、Juliet A. Gerrard、Craig A. Hutton

  DOI：10.1016/j.bmcl.2004.12.043

  日期：2005.2

  Dihydrodipicolinate synthase (DHDPS) is a key enzyme in lysine biosynthesis and an important antibiotic target. The enzyme catalyses the condensation of (S)-aspartate semialdehyde (ASA) and pyruvate to form dihydrodipicolinate. Two new irreversible inhibitors of dihydrodipicolinate synthase are reported, designed to mimic the acyclic enzyme-bound condensation product of ASA and pyruvate. These compounds represent an important new lead in the design of potent inhibitors for this enzyme. (C) 2004 Elsevier Ltd. All rights reserved.