1,4-pentadien-3-oxo-1,5-dicarboxylic acid | 59234-59-2

• 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: 1,4-pentadien-3-oxo-1,5-dicarboxylic acid
• 英文别名: (2E,5E)-4-oxohepta-2,5-dienoic acid；(E,E)-4-oxo-2,5-heptdienedioic acid；4-oxo-hepta-2t,5t-dienedioic acid；4-Oxo-hepta-2t,5t-diendisaeure；4-Oxoheptan-2E,5E-dien-disaeure；(2E,5E)-4-oxohepta-2,5-dienedioic acid
• CAS: 59234-59-2
• 化学式: C₇H₆O₅
• 分子量: 170.122
• InChiKey: FORGRSMNOFWNBO-ZPUQHVIOSA-N

物化性质

• 熔点：
  230 °C
• 沸点：
  406.9±30.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-pentadien-3-oxo-1,5-dicarboxylic acid 在 溴 作用下， 以 溶剂黄146 为溶剂， 以53%的产率得到2,3,5,6-Tetrabromo-4-oxoheptanedioic acid
  参考文献：
  名称：

  A Convenient Synthesis of Halogenated Spiro Bi-2(5H)-Furanones

  摘要：

  A new class of unsaturated simple dibromospirobilactones 3 and 4 has been synthesised on the base of the readily available 3-(2-furyl) acrylic acid.

  DOI：

  10.1080/00397919408011735
• 作为产物：
  描述：

  4-oxo-2,6-dihydroxyheptandioic acid 反应 16.0h， 生成 1,4-pentadien-3-oxo-1,5-dicarboxylic acid
  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

文献信息

• Acid catalyzed aldol condensations of ketones with glyoxylic acid: A simple single-step synthesis of 4-oxo-2,5-heptdienedioic acids
  作者：Ananda S. Amarasekara、Uyen Ha

  DOI：10.1080/00397911.2018.1511998

  日期：2018.10.2

  Abstract The acid catalyzed condensations of ketones with glyoxylic acid at 80 °C, under neat conditions gives 4-oxo-2,5-heptdienedioic acids in 56–88% yield. The solid state photochemical dimerization of 4-oxo-2,5-heptdienedioic acid under UV light gives 2,7-dioxo-tricyclo[6.2.0.03,6]decane-4,5,9,10-tetracarboxylic acid in 90% yield.

  摘要 在纯条件下，酮与乙醛酸在 80 °C 下酸催化缩合得到 4-氧代-2,5-庚二烯二酸，产率为 56-88%。4-氧代-2,5-庚二烯二酸在紫外光下固态光化学二聚反应得到2,7-二氧代-三环[6.2.0.03,6]癸烷-4,5,9,10-四羧酸，产率为90% .
• On the Ring-Opening Reactions of the Furan Compounds. I. The Synthesis of 1,4-Pentadien-3-one-1, 5-dicarboxylic Acid from 2-Furanacrylic Acid
  作者：Hiroshi Midorikawa

  DOI：10.1246/bcsj.26.302

  日期：1953.6

  2-Furanacrylic acid gave 1,4-pentadien-3-one-1,5-dicarboxylic acid in a fairly good yield by treatment with aqueous hydrogen peroxide containing hydrochloric acid. This acid underwent the same photochemical change by direct sunlight as its methyl ester. This acid was reduced to γ-ketopimelic acid hydrazones of the acid by aluminium amalgam, and oxidised to fumaric and oxalic acids by potassium permanganate

  通过用含有盐酸的过氧化氢水溶液处理，2-呋喃丙烯酸以相当好的收率得到1,4-戊二烯-3-one-1,5-二羧酸。这种酸在阳光直射下经历了与其甲酯相同的光化学变化。该酸被铝汞齐还原为该酸的γ-酮吡咯酸腙，并被高锰酸钾氧化为富马酸和草酸。假设两个双键具有反式结构。得到酸和甲酯的苯腙。
• Herstellung von Dihydro-, Tetrahydro- und Hexahydrochelidamsäure-Derivaten
  作者：Kurt Hermann、André S. Dreiding

  DOI：10.1002/hlca.19760590227

  日期：1976.3.10

  Preparation of dihydro-, tetrahydro- and hexahydro-chelidamic-acid derivatives.

  制备二氢-，四氢-和六氢-烯丙基酰胺酸衍生物。
• Asymmetric Synthesis of Complicated Bicyclic and Tricyclic Polypropanoatesvia the DoubleDiels-Alder Addition of 2,2′-Ethylidenebis[3,5-dimethylfuran]
  作者：Chiara Marchionni、Pierre Vogel

  DOI：10.1002/1522-2675(20010228)84:2<431::aid-hlca431>3.0.co;2-w

  日期：2001.2.28

  A new, non-iterative method for the asymmetric synthesis of long-chain and polycyclic polypropanoate fragments starting from 2,2'-ethylidenebis[3,5-dimethylfuran] (2) has been developed. Diethyl (2E,5E)-4-oxohepta-2,5-dienoate (6) added to 2 to give a single meso-adduct 7 containing nine stereogenic centers. Its desymmetrization was realized by hydroboration with (+)-IpcBH(2) (isopinocampheylborane), leading to diethyl (1S,2R,3S,4S,4aS,7R,8R,8aR,9aS,10R,10aR)-1,3,4,7,8,8a,9,9a-octahydro-3-hydroxy-2,4,5,7,10-pentamethyl-9-oxo-2H,10H-2,4a : 7,10a-diepoxyanthracene-1,8-dicarboxylate ((+)-8; 78% e.e.). Alternatively, 7 was converted to meso-(1R,2R,4R,4aR,5S,7S,8S,8aR,9aS,10s,10aS)-1,8-bis(acetoxymethyl)-1,8,8a,9a-tetrahydro-2,4,5,7,10-pentamethly-2H-10H-2,4a :7,10a-diepoxyanthracene-3,6,9(4H,5H,7H)-trione (32) that was reduced enantioselectively by BH3 catalyzed by methyloxazaborolidine 19 derived form L-diphenylprolinol giving (1S,2S,4S,4aS,5S,6R,7R,8R,8aS,9aR,10R,10aS)-1,8-bis(acetoxymethyl)-1,8,8a,9a-tetrahydro-6-hydroxy-2,4,5,7,10-pentamethyl-2H,10H-2,4a :7,10a-diepoxyanthracene-3,9(4H,7H)-dione ((-)-33; 90% e.e.). Chemistry was explored to carry out chemoselective 7-oxabicylo[2.2.1]heptanone oxa-ring openings and intra-ring C-C bond cleavage. Polycclic polypropanoates as (1R,2S,3R,4R,4aR,5S,6R,7S,8R,9R,10R,11S,12aR)-1-(ethoxy-carbonyl)-1,3,4,7,8,9,10,11,12,12a-decahydro-3,11-dihydroxy-2,4,5,7,9-pentamethyl-12-oxo-2H,5H-2,4a :6,9 :6,11-triepoxybenzocyclodecene-10,8-carbolactone (51), (1S,2R,3R,4R,4aS,5S,7S,8R,9R,10R,12S,12aS)-1,10-bis(acet-oxymethyl)tetradecahydro-8-(methoxymethoxy)-2,4,5,7,9-pentamethyl-3,9-bis[[2-(trimethylsilyl)ethoxy]methoxy)-6,11-epoxycyclodecene-4a,6,11,12-tetrol((+)-83), and (1R,2R,3R,4aR,4bR,6S,6R,7R,8R,8aS,9S,10aR)-3,5-bis(acetoxymethyl)-4a,8a-dihydroxy-1-(methoxymethoxy)-2,6,8,9,10a-pentamethyl-2,7-bis([2-(trimethylsilyl)-ethoxy]methoxy)dodecahydrophenanthrene-4,10-dione (85) were obtained in few synthetic steps.
• Generating MODFLOW Grids from Boundary Representation Solid Models
  作者：Norman L. Jones、Trevor J. Budge、Alan M. Lemon、Alan K. Zundel

  DOI：10.1111/j.1745-6584.2002.tb02504.x

  日期：2002.3

  AbstractComplex stratigraphy can be difficult to simulate in MODFLOW models. MODFLOW uses a structured grid that requires that each grid layer be continuous throughout the model domain. This makes it difficult to explicitly represent common features such as pinchouts and embedded seams in a MODFLOW model. In this paper, we describe a method for automatically generating MODFLOW‐compatible grids from boundary‐representation solid models. Solid models are data structures developed originally for computer‐aided design applications that define the geometry of three‐dimensional objects. Solid models can be used to represent arbitrarily complex stratigraphy. The elevations defined by the solids are then extracted from the solids in a manner that preserves the continuous‐layer requirement imposed by MODFLOW. Two basic approaches are described: The first method adjusts the MODFLOW grid dimensions (layer elevations) to fit the solid model boundaries, and the second method creates a regular MODFLOW grid and adjusts the material properties to match the changes in stratigraphy. One of the main benefits of using solid models to define stratigraphy for MODFLOW models is that it provides a grid‐independent definition of the layer elevations that can be used to immediately re‐create the MODFLOW grid geometry after any change to the grid resolution.