5-oxo-octanal | 30880-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-oxo-octanal
• 英文别名: 5-Oxooctanal
• CAS: 30880-59-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: NKKMPIXWEPUSCG-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±23.0 °C(Predicted)
• 密度：
  0.917±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：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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-oxo-octanal 在 palladium dihydroxide 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 毒芹碱
  参考文献：
  名称：

  Kawaguchi, Mamoru; Hayashi, Osamu; Sakai, Noriyuki, Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112

  摘要：

  DOI：
• 作为产物：
  描述：

  1-丙基环戊烯 在 sodium cyanoborohydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-oxo-octanal
  参考文献：
  名称：

  Kawaguchi, Mamoru; Hayashi, Osamu; Sakai, Noriyuki, Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112

  摘要：

  DOI：

文献信息

• Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
  作者：Gary A. Molander、Kimberly O. Cameron

  DOI：10.1021/ja00056a002

  日期：1993.2

  2-(alkoxycarbon)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regioncontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation

  路易斯酸用作 1,4- 和 1,5- 二羰基亲电试剂与 β-二酮和 β-酮酯的双（三甲基甲硅烷基）烯醇醚环化的催化剂。多种 2-(烷氧基碳)-m-氧杂双环[3.n.1]alkan-3-ones 可以通过该过程构建，其中产生两个新的碳-碳键。观察到异常高的区域控制，并且几乎可以在新碳环的每个位置实现良好到出色的立体化学控制。提出分子内相邻基团参与来解释在环化反应中获得的异常高的选择性
• Milieux hyperbasiques
  作者：M. Larchevêque、G. Valette、Th. Cuvigny

  DOI：10.1016/0040-4020(79)88003-5

  日期：1979.1

  Substituted γ and δ-ketoaldehydes may be conveniently synthesized in two steps from imine carbanions, which are obtained by reaction with hyperbasic media. These anions are stable at low temperature (−30°); they react with functional electrophiles to afford masked ketoaldehydes which may be cyclised into various cyclopentenones or cyclohexenones.

  取代的γ和δ-酮醛可以方便地从亚胺碳负离子分两步合成，亚胺碳负离子是通过与高碱性介质反应而获得的。这些阴离子在低温（−30°）下稳定；它们与功能性亲电试剂反应，得到被掩蔽的酮醛，可以将其环化成各种环戊烯酮或环己烯酮。
• <i>N</i>-phenyl-substituted pyrrolidines, piperidines and azabicyclics by a tandem reduction-double reductive amination reaction
  作者：Richard A. Bunce、Derrick M. Herron、Jason R. Lewis、Sharadsrikar V. Kotturi

  DOI：10.1002/jhet.5570400115

  日期：2003.1

  formed in high yield and are easily purified. The method has also been extended to the synthesis of fused N-phenylazabicyclics from 2-(3-oxo-propyl)cycloalkanones. A high degree of diastereoselectivity for the trans-fused product is observed in substrates having an ester group α to the cycloalkanone carbonyl. Bicyclic precursors lacking this ester group give mixtures of cis and trans products. Finally

  通过分别在4-和5-氧醛的存在下催化还原硝基苯来合成N-苯基取代的吡咯烷和哌啶。该方法包括还原芳族硝基以得到N-苯基羟胺或苯胺，然后用两个羰基官能团进行还原胺化。单环体系通常以高收率形成并且易于纯化。该方法还扩展到由2-（3-氧代-丙基）环烷酮合成稠合的N-苯基氮杂双环。在具有相对于环烷酮羰基的酯基为α的底物中，观察到对转熔产物的高度非对映选择性。缺少该酯基的双环前体可得到顺式和反式产品。最后，与以前的报道相反，我们证明了在这些反应中苯胺可以代替硝基苯。
• Novel 3-aroyl-6,7-dihydro-5h-pyrrolo[1,2-c] imidazole-7-carboxylic acid derivatives
  申请人：HISAMITSU PHARMACEUTICAL CO., INC.

  公开号：EP0307034A1

  公开（公告）日：1989-03-15

  A novel 3-aroyl-6,7-dihydro-5H-pyrrolo[1,2-c] imidazole-­7-carboxylic acid derivative which is useful as a medicine having excellent analgesic and anti-inflammatory actions with remarkably less toxicity and side-effects.

  一种新型 3-芳酰基-6,7-二氢-5H-吡咯并[1,2-c]咪唑-7-羧酸衍生物，可作为药物使用，具有极佳的镇痛和消炎作用，且毒性和副作用显著降低。
• Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils
  作者：Gary R. Takeoka、Ron G. Buttery、Charles T. Jr. Perrino

  DOI：10.1021/jf00049a006

  日期：1995.1

  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.