5-(9-methyl nonanoate)-3-phenyl-Δ²-isoxazoline | 394724-67-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(9-methyl nonanoate)-3-phenyl-Δ²-isoxazoline
• 英文别名: Methyl 9-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)nonanoate；methyl 9-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)nonanoate
• CAS: 394724-67-5
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: XWCYRXIJUSFEDM-UHFFFAOYSA-N

物化性质

• 沸点：
  411.9±37.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(9-methyl nonanoate)-3-phenyl-Δ²-isoxazoline 在 镍 氢气 、 硼酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 21.17h， 生成 12-Oxo-12-phenyl-10-trimethylsilanyloxy-dodecanoic acid methyl ester
  参考文献：
  名称：

  还原脂肪酸酯Δ2-异恶唑啉杂环。含有β-羟基酮部分杂环的脂肪酸酯的制备。含有β-羟基酮部分的脂肪酯的制备

  摘要：

  AbstractFatty ester compounds containing the β‐hydroxy ketone moiety were prepared in good yields from their corresponding fatty Δ2‐isoxazoline heterocyclic precursors by a reductive hydrogenolysis‐hydrolysis procedure using Raney nickel as catalyst. By this methodology, C‐17, C‐18, and C‐19 straight‐chain fatty methyl esters containing the 10‐hydroxy 12‐keto moieties were prepared in 73, 83, and 92%, respectively, from their corresponding isoxazoline fatty ester compounds. Two other 10‐hydroxy 12‐keto C‐12 and C‐14 fatty ester compounds were prepared in 84 and 92% yield, respectively. The C‐12 β‐hydroxy ketone contains a phenyl ring at C‐12, whereas the C‐14 β‐hydroxy ketone compound has two methyl substituents at C‐13. GC‐MS using electron impact ionization was used to determine the hydroxyl and ketone positions after conversion of the hydroxyl group into its corresponding trimethylsilyl ether. The precursor fatty ester Δ2‐isoxazolines used in this study are readily available in one step from a 1,3‐dipolar cycloaddition reaction between nitrile oxides and methyl 10‐undecenoate. This overall two‐step sequence, 1,3‐dipolar cycloaddition followed by reductive ring opening, represent a convenient method to construct fatty ester compounds in good yields containing the β‐hydroxy ketone functionality, an outcome not easily accessible by other methods.

  DOI：

  10.1007/s11746-002-0487-5
• 作为产物：
  描述：

  苯甲醛肟 、 10-烯酸甲酯 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到5-(9-methyl nonanoate)-3-phenyl-Δ²-isoxazoline
  参考文献：
  名称：

  Δ2-异恶唑啉脂肪酸酯杂环的合成

  摘要：

  AbstractFatty ester Δ‐2 heterocycles were prepared in good yields and excellent regioselectivity from 1,3‐dipolar cycloaddition reactions between methyl 10‐undecenoate and nitrile oxides. This methodology provides convenient access to the methyl esters of margaric (4b) and stearic (4c) acids in 63–66% yield that contain the isoxazoline heterocycle between C‐10 and C‐12. These fatty heterocycle compounds are synthesized in a one‐pot sequence in which methyl 10‐undecenoate is used to trap the reactive nitrile oxide intermediates that are generated by reacting aldoximes with aqueous sodium hypochlorite and a catalytic amount of triethylamine or by directly reacting hydroximic acid chlorides with a stoichiometric amount of base. The fatty ester Δ2‐isozazoline heterocycles represent a versatile synthon that may be useful to obtain oleochemicals with potentially new and interesting properties not easily accessible by other methods.

  DOI：

  10.1007/s11746-001-0386-9

文献信息

• Synthesis of Δ²-Isoxazoline fatty acid ester heterocycles
  作者：James A. Kenar、Sevim Z. Erhan

  DOI：10.1007/s11746-001-0386-9

  日期：2001.10

  AbstractFatty ester Δ‐2 heterocycles were prepared in good yields and excellent regioselectivity from 1,3‐dipolar cycloaddition reactions between methyl 10‐undecenoate and nitrile oxides. This methodology provides convenient access to the methyl esters of margaric (4b) and stearic (4c) acids in 63–66% yield that contain the isoxazoline heterocycle between C‐10 and C‐12. These fatty heterocycle compounds are synthesized in a one‐pot sequence in which methyl 10‐undecenoate is used to trap the reactive nitrile oxide intermediates that are generated by reacting aldoximes with aqueous sodium hypochlorite and a catalytic amount of triethylamine or by directly reacting hydroximic acid chlorides with a stoichiometric amount of base. The fatty ester Δ2‐isozazoline heterocycles represent a versatile synthon that may be useful to obtain oleochemicals with potentially new and interesting properties not easily accessible by other methods.
• Reduction of fatty ester Δ²-isoxazoline heterocycles. Preparation of fatty esters containing the β-hydroxy ketone moietyheterocycles. Preparation of fatty esters containing the β-hydroxy ketone moiety
  作者：James A. Kenar

  DOI：10.1007/s11746-002-0487-5

  日期：2002.4

  AbstractFatty ester compounds containing the β‐hydroxy ketone moiety were prepared in good yields from their corresponding fatty Δ2‐isoxazoline heterocyclic precursors by a reductive hydrogenolysis‐hydrolysis procedure using Raney nickel as catalyst. By this methodology, C‐17, C‐18, and C‐19 straight‐chain fatty methyl esters containing the 10‐hydroxy 12‐keto moieties were prepared in 73, 83, and 92%, respectively, from their corresponding isoxazoline fatty ester compounds. Two other 10‐hydroxy 12‐keto C‐12 and C‐14 fatty ester compounds were prepared in 84 and 92% yield, respectively. The C‐12 β‐hydroxy ketone contains a phenyl ring at C‐12, whereas the C‐14 β‐hydroxy ketone compound has two methyl substituents at C‐13. GC‐MS using electron impact ionization was used to determine the hydroxyl and ketone positions after conversion of the hydroxyl group into its corresponding trimethylsilyl ether. The precursor fatty ester Δ2‐isoxazolines used in this study are readily available in one step from a 1,3‐dipolar cycloaddition reaction between nitrile oxides and methyl 10‐undecenoate. This overall two‐step sequence, 1,3‐dipolar cycloaddition followed by reductive ring opening, represent a convenient method to construct fatty ester compounds in good yields containing the β‐hydroxy ketone functionality, an outcome not easily accessible by other methods.