methyl (E,E)-5-formyl-2,4-pentadienoate | 40188-21-4

• 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: methyl (E,E)-5-formyl-2,4-pentadienoate
• 英文别名: (2E,4E)-methyl 6-oxohexa-2,4-dienoate；trans, trans-Muconaldehydsaeure-methylester；Methyl-6-oxo-2,4-trans,trans-hexadienoat；methyl (2E,4E)-6-oxohexa-2,4-dienoate
• CAS: 40188-21-4
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: OKCKDXOUJKZELN-ZUVMSYQZSA-N

物化性质

• 熔点：
  81 °C(Solv: water (7732-18-5))
• 沸点：
  237.2±23.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E,E)-5-formyl-2,4-pentadienoate 在 咪唑 、 盐酸 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl (E,E)-6-(tert-butyldimethylsilyloxy)-7-carbamoyl-2,4-heptadienoate
  参考文献：
  名称：

  A new total synthesis of the fungal toxin slaframine

  摘要：

  DOI：

  10.1021/ja00389a030
• 作为产物：
  描述：

  6-羟基己酸甲酯 在 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 10.0h， 以26%的产率得到methyl (E,E)-5-formyl-2,4-pentadienoate
  参考文献：
  名称：

  醇的立体选择性有机催化氧化为烯类：制备多烯的同源方法

  摘要：

  开发了一种新型的通过氧化烯胺催化的有机催化氧化方法，该方法与由简单的饱和醇直接合成烯类具有优异的相容性。通过使用这种胺催化的IBX氧化，广泛的...

  DOI：

  10.1039/c5cc10093c

文献信息

• Deblocking of dithioacetals and oxathioacetals using periodic acid under mild nonaqueous conditions
  作者：Xiao-Xin Shi、Subhash P. Khanapure、Joshua Rokach

  DOI：10.1016/0040-4039(96)00838-6

  日期：1996.6

  A novel method for the deblocking of the dithioacetals and oxathioacetals is described. Periodic acid under nonaqueous conditions has been used for the deprotection of the dithio- and oxathio-derivatives to the corresponding carbonyl compounds. This simple high-yield transformation is conveniently carried out in nonaqueous medium and works well with complex sensitive aldehydes and in the presence of

  描述了用于解封二硫缩醛和草硫缩醛的新方法。非水条件下的高碘酸已用于将二硫代和氧杂硫代衍生物脱保护为相应的羰基化合物。这种简单的高收率转化可在非水介质中方便地进行，并且与复杂的敏感醛以及存在其他保护基时均能很好地发挥作用。
• Delta-hydroxy-beta-lysine derivatives and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0271829A2

  公开（公告）日：1988-06-22

  compound of the formula wherein R' and R4 are independently amino or an organic residue bonded through nitrogen, R2 is hydrogen or alkyl which may be substituted, R3 is hydrogen or a protecting group and R5 is hydroxyl which may be substituted or amino which may be substituted or salts thereof; with the proviso that when R1 is amino, sorbylamino or hexanoylamino, R2 is hydrogen or methyl, R4 is amino which may be protected adn R5 is hydroxyl or 2-amidinoethylamino, R3 is a protecting group, and that when R1 is amino, leucylamino, acetylamino or benzyloxycarbonylamino, R3 is hydrogen, methyl or 2-tettrahydropyranyl, R4 is amino, acetylamino or benzyloxycarbonylamino and R5 is hydroxyl which may be substituted or amino which may be substituted, R2 is alkyl which may be substituted, has antibacterial activities against drug-resistant bacteria and therefore can be useful as a chemotherapeutic drug for bacterial infections in mammals.

  式中的化合物 其中 R' 和 R4 独立地为氨基或通过氮键合的有机残基，R2 为氢或可被取代的烷基，R3 为氢或保护基团，R5 为可被取代的羟基或可被取代的氨基或其盐；但当 R1 为氨基、山梨氨基或己酰氨基时，R2 为氢或甲基，R4 为可被保护的氨基，R5 为羟基或 2-脒乙基氨基，R3 为保护基；当 R1 为氨基、月桂氨基、乙酰氨基或苄氧羰基氨基时，R3 为氢、甲基或 2-四氢吡喃基、R4 是氨基、乙酰氨基或苄氧羰基氨基，R5 是羟基（可被取代）或氨基（可被取代），R2 是烷基（可被取代）时，具有抗耐药细菌的抗菌活性，因此可用作哺乳动物细菌感染的化疗药物。
• A synthetic route to the C4 octadienic esters of trichothecenes from D-glucose
  作者：Deen Bhandu Tulshian、Bert Fraser-Reid

  DOI：10.1021/ja00392a045

  日期：1981.1
• Chloroperoxidase-catalyzed oxidation of conjugated dienoic esters
  作者：Despina J Bougioukou、Ioulia Smonou

  DOI：10.1016/s0040-4039(01)02127-x

  日期：2002.1

  The chloroperoxidase (CPO)-catalyzed oxidations of dienes conjugated to an ester group were studied using tert-butyl hydroperoxide as the terminal oxidant. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes
  作者：Weilin Sun、Patrick J. Carroll、Dianne R. Soprano、Daniel J. Canney

  DOI：10.1016/j.bmcl.2009.05.081

  日期：2009.8

  Attempts to prepare substituted chromones as novel retinoids revealed that some chromones were unstable under Wadsworth-Horner-Emmons reaction conditions. Hence, Wittig reactions were used to prepare chromone-based compounds as potential retinoids. Firstly, Wittig reagents prepared from 3-bromomethyl-chromen-4-one were reacted with olefinic-aldehydes to provide the target compounds with all-trans side chains in good yield. The approach supplies a useful general route to structurally diverse chromone-based compounds possessing a variety of side chains. Sequential Wittig reactions were used also to prepare a chromone-based retinoid. These novel compounds were evaluated in binding assays and a high affinity RAR ligand was identified. Crystal structures obtained for two key precursors aided the interpretation of binding data. (C) 2009 Elsevier Ltd. All rights reserved.