cis-butenedial | 3675-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-butenedial
• 英文别名: cis-2-Butene-1,4-dial；maleic dialdehyde；BDA；Malealdehyde；(Z)-but-2-enedial
• CAS: 3675-13-6
• 化学式: C₄H₄O₂
• 分子量: 84.0746
• InChiKey: JGEMYUOFGVHXKV-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

(E)-2-丁烯二醛是呋喃的人类已知代谢物。

(E)-2-Butenedial is a known human metabolite of furan.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  cis-butenedial 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 羟基-1,4-丁二醛
  参考文献：
  名称：

  6-或7-羟基和6-或7-甲氧基烷烃的合成

  摘要：

  丙酮二羧酸的单甲酯，甲胺盐酸盐和水解的二甲氧基二氢呋喃之间的新型曼尼希式缩合反应得到6或7-官能化的β-酮酯tropanes 12-15。进一步加工得到一系列6-或-7-羟基和6-或7-甲氧基2β-甲氧基羰基-3-芳基托烷。

  DOI：

  10.1016/s0040-4039(97)00087-7
• 作为产物：
  描述：

  2,5-二氢呋喃 在 硫酸 作用下， 反应 5.0h， 生成 cis-butenedial
  参考文献：
  名称：

  Anodic Oxidation of Unsaturated Aliphatic Ethers in aqueous electrolytes

  摘要：

  2,5-dihydrofuran 1 was galvanostatically oxidized in aqueous electrolytes on Pt and PbO2 anodes at current densities of 10 to 50 mA cm(-2). Under acidic conditions maleic dialdehyde 2 was obtained on bath electrodes with a current efficiency (c.e.) of up to 50%. In the alkaline region (pH 10) 4-hydroxy crotonic aldehyde 3 (Pt) or 2,5-dihydrofuranone 4 (PbO2) become the main products with c.e.'s of 29% and 27%, respectively, depending on the anode material. The influence of pH and of the anode material are discussed in detail. 2,3-dihydrofuran 7, vinyl ethyl ether 8 and for comparison, furan 9 were studied in addition.

  DOI：

  10.1002/prac.19943360708

文献信息

• Atmospheric chemistry of benzene oxide/oxepin
  作者：Björn Klotz、Ian Barnes、Karl H. Becker、Bernard T. Golding

  DOI：10.1039/a606152d

  日期：——

  The atmospheric chemistry of benzene oxide/oxepin, a possible intermediate in the atmospheric oxidation of aromatic hydrocarbons, has been investigated in a large volume photoreactor at 298 K and atmospheric pressure using in situ FTIR spectroscopy for the analysis. Rate coefficients of (10.0±0.4)×10 -11 and (9.2±0.3)×10 -12 cm 3 molecule -1 s -1 have been determined for the reaction of benzene oxide/oxepin with OH and NO 3 radicals, respectively. Reaction with OH radicals produces almost exclusively the (E,Z)- and (E,E)-isomers of hexa-2,4-dienedial, whereas reaction with NO 3 produces (Z,Z)-hexa-2,4-dienedial and unidentified organic nitrates. Phenol has been observed as a major product of the thermal decomposition, visible and UV photolysis of benzene oxide/oxepin. The results are discussed in conjunction with the oxidation mechanisms of aromatic hydrocarbons. The major atmospheric sinks of benzene oxide/oxepin will be reaction with OH radicals and photolysis and, under smog chamber conditions with high NO 2 concentrations, also reaction with NO 3 .

  苯氧化物/环氧庚烷的大气化学，作为芳香烃大气氧化可能的中间体，已在298K和大气压下使用现场傅里叶变换红外光谱进行分析的大型体积光反应器中进行了研究。发现苯氧化物/环氧庚烷与OH和NO3自由基反应的速率系数分别为(10.0±0.4)×10-11和(9.2±0.3)×10-12 cm3分子-1 s-1。与OH自由基反应几乎专门生成(E,Z)-和(E,E)-己二烯二醛异构体，而与NO3反应生成(Z,Z)-己二烯二醛和未识别的有机硝酸盐。作为苯氧化物/环氧庚烷热分解、可见光和紫外光解的主要产物，酚已被观察到。研究结果与芳香烃的氧化机理结合讨论。苯氧化物/环氧庚烷的主要大气汇将是与OH自由基的反应和光解，以及在NO2浓度高的烟雾室条件下，也与NO3的反应。
• Gas-phase reaction of OH radicals with benzene: products and mechanism
  作者：Torsten Berndt、Olaf Böge

  DOI：10.1039/b106667f

  日期：——

  The gas-phase reaction of OH radicals with benzene was studied in O2/He mixtures under flow conditions in the temperature range 276–353 K and at pressures of 100 and 500 mbar using on-line FT-IR spectroscopy and GC-MS measurements. The reaction conditions were chosen so that the initially formed OH/benzene adduct predominantly reacted either with O2 or O3. Under conditions of a predominant reaction

  使用在线 FT-IR 光谱和 GC-MS 测量，在 276–353 K 温度范围和 100 和 500 mbar 压力下，在 O2/He 混合物中研究了 OH 自由基与苯的气相反应。选择反应条件以使最初形成的OH/苯加合物主要与O2或O3反应。在 OH/苯加合物与 O2 的主要反应条件下，研究了不同 NO 浓度的产物形成。鉴定产物为六-2,4-二烯二醛、苯酚、硝基苯、对苯醌和乙二醛的异构体。发现少量呋喃。随着 NO 浓度的增加，苯酚产率降低，反式、反式-六-2,4-二烯二烯和硝基苯的产率增加，最大值分别为 0.36 ± 0.02 和 0.11 ± 0.02，分别（100 毫巴，295 K）。发现 0.08 ± 0.02 的对苯醌产率与 NO 浓度无关。在 500 mbar 下，[NO]/[O2] = 1-20 × 10-6 的初始比率在 276-353 K 范围内测量苯酚产率的温度依赖性。对于固定的
• Oxidation of furans with dimethyldioxirane. Interception of malealdehyde and related aldehydes via Wittig reactions
  作者：Brian J. Adger、Collette Barrett、Joseph Brennan、Peter McGuigan、M. Anthony McKervey、Brian Tarbit

  DOI：10.1039/c39930001220

  日期：——

  Unsaturated aldehydes including malealdehyde, generated in acetone by oxidation of furans with dimethyldioxirane, can be trapped efficiently by phosphoranes in Wittig reactions.

  在二甲基二氧杂环丙烷作用下，由呋喃氧化生成的包括马来醛在内的不饱和醛，可通过磷鎓盐参与的维蒂希反应得到有效捕获。
• Chemical Synthesis and Pharmacology of 6- and 7-Hydroxylated 2-Carbomethoxy-3-(<i>p</i>-tolyl)tropanes:  Antagonism of Cocaine's Locomotor Stimulant Effects
  作者：Lianyun Zhao、Kenneth M. Johnson、Mei Zhang、Judith Flippen-Anderson、Alan P. Kozikowski

  DOI：10.1021/jm000141b

  日期：2000.8.1

  synthesis to construct an appropriately functionalized tropane ring followed by use of a Suzuki coupling reaction to introduce the aryl group at position 3. Reduction of the resulting tropene by use of SmI(2) or by catalytic hydrogenation followed by deprotection delivered the final target compounds. Some of these compounds were found to retain considerable affinity as inhibitors of the dopamine transporter

  在我们努力确定可能充当可卡因拮抗剂或可卡因部分激动剂的分子的过程中，人们努力利用我们先前关于7-甲氧基化拟可卡因类似物作为弱可卡因功能拮抗剂的能力的发现。本文中，制备了一系列具有环烷环的船形或椅子构型的6-和7-羟基化WIN类似物，并测试了它们取代[（3H）] mazindol结合并抑制高亲和力单胺摄取的能力。大鼠脑神经末梢。这些6和7羟基化的WIN类似物很容易通过经典的Willstätter合成来构建适当官能化的tropane环，然后使用Suzuki偶联反应在3位引入芳基来制备。通过使用SmI（2）或催化氢化，再进行脱保护反应，还原所得的托品，得到最终的目标化合物。发现这些化合物中的某些保留作为多巴胺转运蛋白（DAT）和去甲肾上腺素转运蛋白（NET）的抑制剂具有相当大的亲和力，但它们不是血清素转运蛋白（SERT）的有效抑制剂。本系列化合物均未显示[（3）H] mazindol结合与[（3）H]
• Comparative Metabolism of Furan in Rodent and Human Cryopreserved Hepatocytes
  作者：Leah A. Gates、Martin B. Phillips、Brock A. Matter、Lisa A. Peterson

  DOI：10.1124/dmd.114.057794

  日期：2014.7

  Furan is a liver toxicant and carcinogen in rodents. Although humans are most likely exposed to furan through a variety of sources, the effect of furan exposure on human health is still unknown. In rodents, furan requires metabolism to exert its toxic effects. The initial product of the cytochrome P450 2E1-catalyzed oxidation is a reactive α , β -unsaturated dialdehyde, cis -2-butene-1,4-dial (BDA). BDA is toxic and mutagenic and consequently is considered responsible for the toxic effects of furan. The urinary metabolites of furan in rats are derived from the reaction of BDA with cellular nucleophiles, and precursors to these metabolites are detected in furan-exposed hepatocytes. Many of these precursors are 2-( S -glutathionyl)butanedial-amine cross-links in which the amines are amino acids and polyamines. Because these metabolites are derived from the reaction of BDA with cellular nucleophiles, their levels are a measure of the internal dose of this reactive metabolite. To compare the ability of human hepatocytes to convert furan to the same metabolites as rodent hepatocytes, furan was incubated with cryopreserved human and rodent hepatocytes. A semiquantitative liquid chromatography with tandem mass spectrometry assay was developed for a number of the previously characterized furan metabolites. Qualitative and semiquantitative analysis of the metabolites demonstrated that furan is metabolized in a similar manner in all three species. These results indicate that humans may be susceptible to the toxic effects of furan.

  呋喃在啮齿动物中是一种肝毒物和致癌物。尽管人类很可能通过多种途径接触到呋喃，但呋喃暴露对人类健康的影响尚不清楚。在啮齿动物中，呋喃需要经过代谢才能发挥其毒性作用。细胞色素P450 2E1催化的氧化作用的初始产物是一种活性α,β-不饱和二醛，即顺-2-丁烯-1,4-二醛（BDA）。BDA具有毒性和诱变性，因此被认为是导致呋喃毒性效应的原因。大鼠尿液中的呋喃代谢物来源于BDA与细胞亲核体的反应，这些代谢物的前体在呋喃暴露的肝细胞中被检测到。许多这些前体是2-(S-谷胱甘肽基)丁二醛-胺交联物，其中的胺是氨基酸和多胺。由于这些代谢物来源于BDA与细胞亲核体的反应，它们的水平可以作为这种活性代谢物内部剂量的衡量标准。为了比较人肝细胞与啮齿动物肝细胞将呋喃转化为相同代谢物的能力，将呋喃与冷冻保存的人和啮齿动物肝细胞一起孵育。开发了一种半定量的液相色谱-串联质谱法，用于检测先前鉴定的一些呋喃代谢物。对这些代谢物的定性和半定量分析表明，呋喃在所有三种物种中以类似方式被代谢。这些结果表明，人类可能对呋喃的毒性作用敏感。

表征谱图