cis-4-oxo-2-pentenal | 34218-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-4-oxo-2-pentenal
• 英文别名: cis-4-oxo-pent-2-enal；(Z)-4-oxopent-2-enal
• CAS: 34218-22-9
• 化学式: C₅H₆O₂
• 分子量: 98.1014
• InChiKey: GBLMMVFQENXAFZ-IHWYPQMZSA-N

物化性质

• 沸点：
  199.5±23.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-4-oxo-2-pentenal 在 sodium tetrahydroborate 作用下， 以 盐酸 、 phosphate buffer 为溶剂， 反应 8.0h， 生成 7-(2-hydroxypropyl)-5,6,7,9-tetrahydro-9-oxoimidazo[1,2-a]purine
  参考文献：
  名称：

  Liquid Chromatography−Electrospray Ionization Mass Spectrometric Detection of an Ethenodeoxyguanosine Adduct and Its Hemiaminal Precursors in DNA Reacted with α-Acetoxy-N-nitrosopiperidine and cis-4-Oxo-2-pentenal

  摘要：

  N-Nitrosopiperidine, a carcinogenic cyclic nitrosamine that occurs in the diet and may be formed endogenously, is believed to be metabolically activated by alpha-hydroxylation. The DNA reactive compounds that could be formed in this process have been studied using alpha-acetoxy-N-nitrosopiperidine as a model, Previous studies have shown that 4-oxo-2-pentenal is one product of the hydrolysis of alpha-acetoxyNPIP and that it reacts with deoxyguanosine to produce 7-(2-oxopropyl)-5,9-dihydro-9-oxo-3-beta-D-(7-(2-oxopropyl)-1,N-2-ethenodG). Several other products were formed in that reaction, and these have now been identified as diastereomers of 7-(2-oxopropyl)-5-hydroxy-5,6,7,9-tetrahydro-9-oxo-3-beta-D-deoxyribofuranosylimidazo[1,2-a]purine, the hemiaminal precursors to 7-(2-oxopropyl)-1,N-2-ethenodG. Their structures were characterized by electrospray ionization mass spectrometry (ESI-MS), and by reduction with NaBH4 followed by hydrolysis to 7-(2-hydroxypropyl)-5,6,7,9-tetrahydro-9-oxoimidazo[1,2-a]purine, which was characterized by H-1-NMR, MS, and UV. The presence of 7-(2-oxopropy)-1,N-2-ethenodG and its hemiaminal precursors in DNA reacted with either alpha-acetoxy-N-nitrosopiperidine or cis-4-oxo-2-pentenal was confirmed by LC-ESI-MS and LC-ESI-MS/MS. The results of this study demonstrate that ethenodG adducts and their precursors are present in DNA reacted with alpha-acetoxy-N-nitrosopiperidine, which suggests a possible basis for the unique carcinogenic properties of this nitrosamine.

  DOI：

  10.1021/tx950206r
• 作为产物：
  描述：

  2,5-二氢-2,5-二甲氧基-2-甲基呋喃 在 硫酸 作用下， 生成 cis-4-oxo-2-pentenal
  参考文献：
  名称：

  闪蒸真空热取代取代的三环[5.2.1.0 2,6 ]癸烯的立体特异性全合成（±）戊霉素

  摘要：

  描述了从呋喃开始合成4-官能化的三环[5.2.1.0 2,6 ]癸烯。这些结构被证明是用于合成环戊烯类化合物如戊霉素和类似物的合适的前体。

  DOI：

  10.1016/0040-4039(82)80158-5

文献信息

• First Exclusive Regioselective Fragmentation of Primary Ozonides Controlled by Remote Carbonyl Groups and a New Method for Determining the Regiochemistry of Carbonyl Oxide Formation
  作者：Hsien-Jen Wu、Chu-Chung Lin

  DOI：10.1021/jo952284p

  日期：1996.1.1

  The first exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups on ozonolysis of norbornene derivatives and reaction of final ozonides with triethylamine as a new probe for determining the regiochemistry of carbonyl oxide formation from primary ozonide fragmentation are reported. Ozonolysis of the endo adducts 3a-d and the deuterated compounds 8a and 8b in

  据报道，在降冰片烯衍生物的臭氧分解中，由远端羰基控制的伯氮氧化物的第一个排他性区域选择性断裂是最终的臭氧化物，以及最终的臭氧化物与三乙胺的反应，作为确定伯臭氧化物断裂形成羰基氧化物的区域化学的新探针。内加合物3a-d和氘代化合物8a和8b在CDCl（3）中于-78摄氏度进行臭氧分解，分别得到最终的臭氧化物4a-d，9a和9b作为唯一产物（> 95％）。没有获得可检测量的异构的最终臭氧化物5、10、11和12。提出了一种机制来解释初级臭氧化物的排他性区域选择性断裂。3a-d，8a的臭氧分解 在-78℃下在CH（2）Cl（2）中添加8b和8b，然后分别用三乙胺处理，分别以85-90％的收率得到凸四氧杂环己烷笼化合物16a-d，19a和19b。没有获得可检测量的其他区域异构体17a-d，20a和20b。在-78℃下于CH（2）Cl（2）中对3a-d，8a和8b进行臭氧分解，然后用二甲基硫醚还原，
• Synthesis of Diacetal Trioxa-cage Compounds via Reaction of Bicyclo[2.2.1]heptenes and Bicyclo[2.2.2]octenes with Dimethyldioxirane
  作者：Hui-Chang Lin、Hsien-Jen Wu

  DOI：10.1016/s0040-4020(99)00997-7

  日期：2000.1

  A new entry for the synthesis of diacetal trioxa-cage compounds via oxirane-induced sequential cyclization reaction of 2,3-bis-endo-diacylbicyclo[2.2.1]-5-heptenes and 2,3-bis-endo-diacylbicyclo[2.2.2]-5-octenes is reported. In the case of bicyclo[2.2.2]octenes, sequential cyclization reaction induced by iodine as electrophile failed. We have also demonstrated that dimethyldioxirane can selectively

  通过环氧乙烷诱导的2,3-双-内-二酰基双环[2.2.1] -5-庚烯和2,3-双-内-二酰基双环[2.2 ]的环氧乙烷顺序环化反应合成二缩醛三氧杂笼化合物的新方法.2] -5-辛烯的报道。在双环[2.2.2]辛烯的情况下，碘作为亲电试剂引起的顺序环化反应失败。我们还证明了二甲基二环氧乙烷可以选择性地氧化半缩醛以产生具有完整仲羟基的内酯。
• Titanium Silicalite 1 (TS-1) Catalyzed Oxidative Transformations of Furan Derivatives with Hydrogen Peroxide
  作者：Joos Wahlen、Bart Moens、Dirk E. De Vos、Paul L. Alsters、Pierre A. Jacobs

  DOI：10.1002/adsc.200303185

  日期：2004.2

  The oxidation of furan derivatives with titanium silicalite 1 (TS-1) and hydrogen peroxide is described. Oxidation products are identified and possible reaction pathways are discussed. It is shown that the oxidation of these compounds occurs via epoxidation of one of the furan double bonds. The initially formed epoxides immediately undergo rearrangement, furans yielding unsaturated 1,4-dicarbonyl compounds

  描述了用钛硅沸石1（TS-1）和过氧化氢氧化呋喃衍生物。确定了氧化产物并讨论了可能的反应途径。结果表明，这些化合物的氧化是通过呋喃双键之一的环氧化发生的。最初形成的环氧化物立即发生重排，呋喃产生不饱和的1,4-二羰基化合物，糠醇产生6-羟基-2 H-吡喃-3（6 H）-one。后者的化合物源自中间烯二酮醇的环化。提出的方法特别适用于将2,5-二甲基呋喃氧化为3-己烯-2,5-二酮并将糠醇转化为6-羟基-2 H-吡喃3（6 H）-一，有机合成中的通用合成子。
• Oxidation of furans with dimethyldioxirane
  作者：Brian M. Adger、Collette Barrett、Joseph Brennan、M. Anthony McKervey、R. W. Murray

  DOI：10.1039/c39910001553

  日期：——

  Dimethyldioxirane reacts rapidly at room temperature in acetone with a variety of furans, furnishing in high yield products of oxidative ring opening and, with 2-furanmethanol, 2H-pyran-3(6H)-one via subsequent ring closure.

  二甲基二噁烷在室温下与多种呋喃在丙酮中快速反应，生成氧化开环的高产率产物，且与2-呋喃甲醇反应后可通过后续的环闭合生成2H-吡喃-3(6H)-酮。
• Synthesis of Pentaoxa[5]peristylanes
  作者：Hsien-Jen Wu、Chung-Yi Wu

  DOI：10.1021/jo982049h

  日期：1999.3.1

  tetraacetal tetraoxa cages 11 and 12. Various reaction conditions have been used to optimize the overall yield for the synthesis of methyl group substituted pentaoxa[5]peristylane 7d. Ozonolysis of 6d in CDCl(3) at -78 degrees C without reduction was performed to study the ozonolysis chemistry of the triacylnorbornenes 6a-d. The synthesis of the parent (unsubstituted) compound 25 of pentaoxa[5]peristylane

  烷基取代的五氧杂戊环[5]过氧化炔烃的合成已通过2，3-双-内--7-抗-三酰基吲哚冰片6a-d的臭氧分解反应以及四缩醛四氧杂笼11和12的直接化学转化完成。已用于优化合成甲基取代的五氧杂[5]过氧化亚烷基7d的总收率。在-78摄氏度下进行CDCl（3）中6d的臭氧分解而不还原，以研究triacyInorbornenes 6a-d的臭氧分解化学。五氧杂环戊并[5]过氧杂环戊烷的母体（未取代）化合物25的合成已通过三步有效序列完成，三苯乙缩醛24进行了臭氧分解，总收率最高为45％。通过X射线分析母体化合物25。