diethyl (E,E)-4-oxohepta-2,5-diene-1,7-dioate | 59234-62-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl (E,E)-4-oxohepta-2,5-diene-1,7-dioate
• 英文别名: diethyl (E,E)-4-oxo-2,5-heptadienedioate；diethyl (E,E)-4-oxohepta-2,5-dienedioate；diethyl (2E,5E)-4-oxohepta-2,5-dienoate；4-Oxoheptan-2E,5E-dien-disaeure-diethylester；diethyl (2E,5E)-4-oxohepta-2,5-dienedioate
• CAS: 59234-62-7
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: LHMUOUUDFCOZNB-KQQUZDAGSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  322.0±27.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 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,E)-4-oxohepta-2,5-diene-1,7-dioate 在 水 作用下， 生成 4-oxo-2,6-dihydroxyheptandioic 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
• 作为产物：
  描述：

  4-氧代庚二酸二乙酯 在 溴 、 三乙胺 作用下， 生成 diethyl (E,E)-4-oxohepta-2,5-diene-1,7-dioate
  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

• 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.
• Synthesis of 2,3,4,5-tetra-substituted pyrroles via a base-promoted double Michael reaction of oxime-enoates with nitroolefins
  作者：Yusuke Kuroda、Kazuto Imaizumi、Ken-ichi Yamada、Yosuke Yamaoka、Kiyosei Takasu

  DOI：10.1016/j.tetlet.2013.05.100

  日期：2013.7

  A new method of synthesizing 2,3,4,5-tetra-substituted pyrroles from oxime-enoates with nitroolefins is described. This reaction involves a base-promoted double Michael reaction, followed by dehydrative aromatization. (C) 2013 Elsevier Ltd. All rights reserved.
• The simultaneous double Diels-Alder addition of 1,1-bis(3,5-dimethylfur-2-yl)ethane; toward a new, asymmetric synthesis of long-chain polypropionate fragments and analogues
  作者：Chiara Marchionni、Pierre Vogel、Pietro Roversi

  DOI：10.1016/0040-4039(96)00771-x

  日期：1996.6

  The double cycloaddition of 1,1-bis(3,5-dimethylfur-2-yl)ethane to diethyl (E,E)-4-oxohepta-2,5-diene-1,7-dioate gave a single bis-adduct, the hydroboration of which with IpcBH(2) allows the creation of optically active polycyclic systems that are potential precursors of long-chain polypropionate fragments. (C) 1996 Published by Elsevier Science Ltd
• Total, asymmetric synthesis of ethyl d-ido-4-heptulosuronate derivatives starting from diethyl 4-oxopimelate
  作者：Sandrine Lemaire-Audoire、Pierre Vogel

  DOI：10.1016/s0957-4166(99)00120-2

  日期：1999.4

  Bromination of diethyl 4-oxopimelate, followed by double elimination of HBr and ketalization provided diethyl (E,E)-4,4-(ethylidenedioxy)hepta-2,5-dienedioate 4. Sharpless asymmetric dihydroxylation of 4 produced diethyl (2S,3S)-4,4-(ethylidenedioxy)-2,3-dihydroxyhept-5-eneiodate (+)-5, with 78% e.e. The corresponding tetrol could not be obtained in one step. Silylation of (+)-5 and a second asymmetric dihydroxylation, followed by silylation led to 20% of meso-diester 9 and 60% of diethyl (2S,3S,5S,6S)-2,3,5,6-tetrakis[(t-butyl) 4,4-(ethylidenedioxy)heptanedioate (-)-10. Reductive desymmetrization of (-)-10 with DIBAL-H furnished, after selective oxidation, ethyl (2S,3S,5S,6S)-2,3,5,6-tetrakis-[(t-butyl oxoheptanoate (+)-13 which was then converted into ethyl 1,2,3,6-0-tetraacetyl-4,4-ethylidenedioxy-alpha- and beta-D-ido-heptapyranuronate (-)-15 alpha,beta and into the corresponding 3-(alpha-D-pyranosyl)propene (-)-16. (C) 1999 Elsevier Science Ltd. All rights reserved.