5-oxononanal | 111183-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-oxononanal
• CAS: 111183-86-9
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: ZQVGQOFUOCVQCS-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 12 Torr)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  5-oxononanal 在 ((CF₃)2CHO)2Ti((R)-[1,1-binaphthyl]-2,2'-diolate) (i-C₃H₇)SB(C₂H₅)2 、 Sn(IV) triflate 、 苯基硫三甲基硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (1R,6S)-1-Butyl-8-methylene-10-oxa-bicyclo[4.3.1]decane
  参考文献：
  名称：

  Sequential Catalytic Asymmetric Allylic Transfer Reaction: Enantioselective and Diastereoselective Construction of Tetrahydropyran Units

  摘要：

  DOI：

  10.1002/1521-3773(20020104)41:1<161::aid-anie161>3.0.co;2-n
• 作为产物：
  描述：

  壬烷-1,5-二醇 在 pyridinium chlorochromate 作用下， 生成 5-oxononanal
  参考文献：
  名称：

  Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils

  摘要：

  As part of our efforts to identify volatile decomposition products in used frying oils, a series of 4- and 5-oxoaldehydes were synthesized, purified, and characterized by gas chromatography, gas chromatography-mass spectrometry, gas chromatography-Fourier transform infrared spectrometry, and nuclear magnetic resonance spectrometry. Oxoaldehydes have been proposed as possible precursors of alkylfurans, which have potential anticancer effects. In a model reaction 4-oxononanal was refluxed in hexane for 40 days and only trace amounts of 2-pentylfuran were produced, suggesting that it is not a major precursor of the furan. The volatile constituents of used frying oils obtained from commercial food processors were studied, and 4-oxohexanal, 4-oxooctanal, 4-oxononanal, and 4-oxodecanal were identified.

  DOI：

  10.1021/jf00049a006

文献信息

• 1,5-Dicarbonyl-Verbindungen durch Michael-Addition deprotonierter Enamine und Allylamine an 2-(<i>N</i>-Methylanilino)-acrylnitril
  作者：Hubertus Ahlbrecht、Manfred Dietz、Lothar Weber

  DOI：10.1055/s-1987-27904

  日期：——

  1,5-Dicarbonyl Compounds via Michael-Addition of Deprotonated Enamines and Allylamines to 2-(N-Methylanilino) acrylonitrile A new method for the synthesis of the title compounds by a onepot, three component, coupling reaction is described. Is consists of the reaction of a homoenolate anion and an enol cation equivalent with subsequent alkylation of an acyl-anion equivalent. Hence the methodology of Umpolung is used in a threefold manner within the reaction sequence.

  经由迈克尔加成反应合成1,5-二羰基化合物：通过去质子化的烯胺和烯丙胺对2-(N-甲基苯胺基)丙烯腈的反应。描述了一种新的合成标题化合物的一锅法、三组分偶联反应方法。该方法包括一个同烯醇盐负离子和一个烯醇正离子等价物的反应，随后是酰基负离子等价物的烷基化反应。因此，在反应序列中，极性反转策略被以三种不同的方式应用。
• Regulation of equilibria in the catalytic asymmetric allylic transfer reaction: unusual 1,2-carbonyl addition of 3-trimethylsilyl-2-propenylstannaneElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b304356h/
  作者：Chan-Mo Yu、Ji-Min Kim、Mi-Sook Shin、Mee-Ok Yoon

  DOI：10.1039/b304356h

  日期：——

  Catalytic enantioselective addition of 3-trimethylsilyl-2-propenylstannane to aldehydes promoted by BINOL–Ti(IV) catalyst along with synergistic reagent provides unusual 1,2-adducts with high levels of enantioselectivity.

  由BINOL–Ti(IV)催化剂促进的3-三甲基硅基-2-丙烯基锡酸盐与醛的催化手性选择性加成反应，同时使用协同试剂，生成了具有较高手性选择性的非凡1,2-加成产物。
• Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
  作者：Sandra Hernández-Ibáñez、Ana Sirvent、Miguel Yus、Francisco Foubelo

  DOI：10.3390/molecules28052414

  日期：——

  using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with β-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization are key steps of this methodology

  描述了使用手性 N-叔丁亚磺酰亚胺作为反应中间体的 1-取代同托烷酮的立体控制合成。有机锂和格氏试剂与羟基 Weinreb 酰胺的反应、从酮醛形成化学选择性 N-叔丁亚磺酰基醛亚胺、与这些醛亚胺的 β-酮酸的脱羧曼尼希反应，以及有机催化的 L-脯氨酸分子内曼尼希环化是该方法的关键步骤. 通过合成天然产物 (-)-adaline 及其对映异构体 (+)-adaline，证明了该方法的实用性。
• A dinickel-catalyzed three-component cycloaddition of vinylidenes
  作者：Annah E. Kalb、Mingxin Liu、Megan I. Bosso、Christopher Uyeda

  DOI：10.1039/d2sc02696a

  日期：——

  equivalents and a vinylidene. The resulting methylenedioxolane products can be deprotected in one pot under acidic conditions to reveal α-hydroxy ketones. This method provides convenient access to unsymmetrical alkyl-substituted α-hydroxy ketones, which are challenging to synthesize selectively using cross-benzoin reactions. Mechanistic studies are consistent with an initial migratory insertion of the

  二镍催化剂促进两个醛当量和一个亚乙烯基的[2+2+1]-环加成。所得亚甲基二氧戊环产物可在酸性条件下一锅脱保护以显示α-羟基酮。该方法可以方便地获得不对称烷基取代的α-羟基酮，而使用交叉苯偶姻反应选择性合成这些酮具有挑战性。机理研究与醛最初迁移插入二镍桥接亚乙烯基中一致。插入第二个醛，然后进行 C-O 还原消除，得到环加合物。在稀释条件下，由于所提出的金属环中间体的竞争性β-氢化物消除而产生烯酮副产物。提出了与亚甲基二氧戊环和烯酮的浓度依赖性形成一致的DFT模型。
• 10.1002/ejoc.202400556
  作者：Bagkavou, Georgia G.、Stathakis, Christos I.

  DOI：10.1002/ejoc.202400556

  日期：——

  The direct Cα−Cβ cleavage of allylic alcohols under mild aerobic conditions is presented. The method constitutes a special case of the Mukaiyama hydration reaction, where the presence of a free hydroxyl group in the nearby carbon alters the fate of the reaction leading to the oxidative braking of Cα−Cβ bond. A broad selection of allylic alcohols has been examined and found to deliver useful for further

  提出了在温和有氧条件下烯丙醇的直接 C α -C β裂解。该方法构成了 Mukaiyama 水合反应的一个特例，其中附近碳中游离羟基的存在改变了反应的命运，导致 C α -C β键的氧化断裂。多种烯丙醇经过检验，发现可用于进一步功能化产品，且收率良好至优异。初步的机理研究使我们能够提出一条可能导致碎片产物的合理途径。