5-hydroxy pentanal oxime | 61862-52-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-hydroxy pentanal oxime
• 英文别名: 5-hydroxypentanal oxime；5-hydroxy-valeraldehyde-oxime；5-Hydroxy-valeraldehyd-oxim；5-Hydroxy-valeraldoxim；5-Oximino-1-pentanol；(E)-5-hydroxypentanal oxime；(5Z)-5-hydroxyiminopentan-1-ol
• CAS: 61862-52-0
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: YWEKQYZNCOGVBB-XQRVVYSFSA-N

物化性质

• 沸点：
  260.1±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy pentanal oxime 在 三溴化磷 、 苯 作用下， 生成 5-溴戊腈
  参考文献：
  名称：

  Gerecs; Windholz, Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 14, p. 333,335

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 盐酸 、 氢氧化钾 、 盐酸羟胺 作用下， 生成 5-hydroxy pentanal oxime
  参考文献：
  名称：

  Paul, Bulletin de la Societe Chimique de France, 1934, vol. <5> 1, p. 971,979

  摘要：

  DOI：

文献信息

• A General Synthetic Procedure for N-Unsubstituted Isoxazolidines<i>via</i>Nitrone-Olefin Cycloaddition. Remarkable Catalytic Effect of Bu₂SnO
  作者：Atsushi Abiko

  DOI：10.1246/cl.1995.357

  日期：1995.5

  The remarkable catalysis of Bu2SnO for nitrone formation in the nitrone-olefin cycloaddition reaction has been discovered, and has led to the development of a general method for the synthesis of N-unsubstituted isoxazolidine derivatives.

  发现了Bu2SnO在亚硝基烯烃环加成反应中催化亚硝基形成的显著作用，这导致了一种合成N-无取代异噁唑烷衍生物的通用方法的发展。
• Addition of organolithium compounds to N-thp protected nitrone
  作者：Anwer Basha、James D. Ratajczyk、Dee W. Brooks

  DOI：10.1016/s0040-4039(00)79375-0

  日期：1991.7

  A novel synthesis of a-branched primary hydroxylamines by addition of organolithium reagents to N-THP protected nitrone is described.

  描述了一种通过向N-THP保护的硝酮中添加有机锂试剂来合成α-支链伯羟胺的新方法。
• Dipolar cycloaddition reactions of N-tetrahydropyranylnitrone
  作者：Shadreck Mzengeza、Ralph A. Whitney

  DOI：10.1039/c39840000606

  日期：——

  Paraformaldehyde and the oxime of 5-hydroxypentanal react with alkenes at elevated temperatures to give dipolar cycloadducts arising from N-tetrahydropyran-2-ylnitrone.

  多聚甲醛和5-羟基戊醛的肟在高温下与烯烃反应，生成由N-四氢吡喃-2-基硝基生成的偶极环加合物。
• Structure−Activity Relationships of <i>N</i>-Hydroxyurea 5-Lipoxygenase Inhibitors
  作者：Andrew O. Stewart、Pramila A. Bhatia、Jonathan G. Martin、James B. Summers、Karen E. Rodriques、Michael B. Martin、James H. Holms、Jimmie L. Moore、Richard A. Craig、Teodozyj Kolasa、James D. Ratajczyk、Hormoz Mazdiyasni、Francis A. J. Kerdesky、Shari L. DeNinno、Robert G. Maki、Jennifer B. Bouska、Patrick R. Young、Carmine Lanni、Randy L. Bell、George W. Carter、Clint D. W. Brooks

  DOI：10.1021/jm9700474

  日期：1997.6.1

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.
• Tandem addition-cycloaddition reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene as a method for 4-piperidone synthesis
  作者：Bryan H. Norman、Yves Gareau、Albert Padwa

  DOI：10.1021/jo00006a036

  日期：1991.3

  The reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords 7-oxa-1-azanorbornanes in high yield. The formation of the bicyclic isoxazolidine involves conjugate addition of the oxime onto the diene to give a transient nitrone that then undergoes a subsequent intramolecular dipolar cycloaddition reaction. The coupling of several oximes with divinyl sulfone was also studied, and related cycloadducts were obtained in excellent yield. The stereochemistry of the cycloaddition is best explained in terms of an exclusive reaction of the Z isomer of the nitrone via an easily attainable endo orientation of the reactive groups. Molecular mechanics calculations have been refined to accurately predict the regiochemistry of the intramolecular cycloaddition. Treatment of these 7-oxa-1-azanorbornanes with Raney nickel in methanol results in reductive nitrogen-oxygen bond cleavage to give substituted 4-piperidones. The bicyclic isoxazolidine derived from cyclohexanone oxime and bis(phenyl-sulfonyl)diene was converted to the azaspiro[5.5]undecane ring system, which is representative of the key ring skeleton of the perhydrohistrionicotoxin family of alkaloids.