trans-5-ethoxy-3-phenyl-N-methyl isoxazolidine | 83077-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: trans-5-ethoxy-3-phenyl-N-methyl isoxazolidine
• 英文别名: (3S,5S)-5-ethoxy-2-methyl-3-phenyl-1,2-oxazolidine
• CAS: 83077-18-3
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: NHILOZCLSIHIMC-RYUDHWBXSA-N

物化性质

• 沸点：
  145 °C(Press: 1 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-5-ethoxy-3-phenyl-N-methyl isoxazolidine 、 碘甲烷 在 sodium hydroxide 作用下， 生成 3-Dimethylamino-3-phenyl-propionsaeureethylester
  参考文献：
  名称：

  Synthese von 4-Alkoxy- und 3-nitrosubstituierten Isoxazolidinen durch katalysierte 1,3-dipolare Cycloadditionsreaktionen von Nitronen mit Vinylethern und Nitroolefinen

  摘要：

  1,3-Dipolar cycloadditions of the C-phenyl-N-alkylnitrones 1,3 and the C,N-diphenylnitrone (2) with vinyl ethers 5,6 are strongly catalyzed by chiral oxazaborolidines derived from N-arylsulfonyl substituted L-alpha-amino acids valine and tert-butyl leucine and BH3 . THF complex at -22 degrees C to room temperature to give predominantly the 3,5-trans-substituted 5-alkoxy-isoxazolidines 8b - 12b, but with moderate enantioselectivity. Thermal cycloaddition afforded predominantly the 3,5-cis-substituted 5-alkoxy-isoxazolidines 8a - 12a. The cycloaddition of (E)-1-ethyl-2-nitroethene (7) afforded a mixture of cis- and trans-substituted 4-nitro-isoxazolidines 13. The ratio depends on reaction temperature and catalyst. Mild ring cleavage after quarternization of 5-ethoxy-2-methyl-isoxazolidines (8) yields the corresponding beta-amino-esters 27, 28.

  DOI：

  10.1002/prac.19973390175
• 作为产物：
  描述：

  N-methyl-α-phenylnitrone 、 乙烯基乙醚 在 (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 57.0h， 以44%的产率得到cis-5-ethoxy-3-phenyl-N-methyl isoxazolidine
  参考文献：
  名称：

  Synthese von 4-Alkoxy- und 3-nitrosubstituierten Isoxazolidinen durch katalysierte 1,3-dipolare Cycloadditionsreaktionen von Nitronen mit Vinylethern und Nitroolefinen

  摘要：

  1,3-Dipolar cycloadditions of the C-phenyl-N-alkylnitrones 1,3 and the C,N-diphenylnitrone (2) with vinyl ethers 5,6 are strongly catalyzed by chiral oxazaborolidines derived from N-arylsulfonyl substituted L-alpha-amino acids valine and tert-butyl leucine and BH3 . THF complex at -22 degrees C to room temperature to give predominantly the 3,5-trans-substituted 5-alkoxy-isoxazolidines 8b - 12b, but with moderate enantioselectivity. Thermal cycloaddition afforded predominantly the 3,5-cis-substituted 5-alkoxy-isoxazolidines 8a - 12a. The cycloaddition of (E)-1-ethyl-2-nitroethene (7) afforded a mixture of cis- and trans-substituted 4-nitro-isoxazolidines 13. The ratio depends on reaction temperature and catalyst. Mild ring cleavage after quarternization of 5-ethoxy-2-methyl-isoxazolidines (8) yields the corresponding beta-amino-esters 27, 28.

  DOI：

  10.1002/prac.19973390175

文献信息

• 1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines
  作者：Jean-Paul G. Seerden、Mike M.M. Boeren、Hans W. Scheeren

  DOI：10.1016/s0040-4020(97)00757-6

  日期：1997.8

  The 1,3-dipolar cycloaddition reactions of various Z- and E-nitrones with ethyl vinyl ether and 2,3-dihydrofuran are catalyzed by 20 mol% of chiral oxazaborolidines at room temperature. The effect of high pressure on these reactions is discussed.

  在室温下，由20mol％的手性恶唑硼烷环烷催化各种Z-和E-硝酮与乙基乙烯基醚和2，3-二氢呋喃的1，3-偶极环加成反应。讨论了高压对这些反应的影响。
• Tricarbonyl(benzaldehyde)chromium(0) complexes in organic synthesis: A highly stereoselective 1,3-dipolar cycloaddition of chromium(0)-complexed nitrones
  作者：Chisato Mukai、Jea Cho Won、Jong Kim In、Miyoji Hanaoka

  DOI：10.1016/s0040-4039(00)97200-9

  日期：1990.1

  The 1,3-dipolar cycloaddition of chromium(0)-complexed nitrones (10, 11) with electron-rich olefins (2) provided, after decomplexation with CAN, -3,5-disubstituted isoxazolidines (-14, 15) in a highly stereoselective as well as regioselective manner.

  铬（0）-complexed硝酮的1,3-偶极环加成（10，11）与富电子烯烃（2）提供，具有CAN解络后，-3,5-二取代的异恶唑烷（- 14，15）是一个高度立体选择性以及区域选择性的方式。
• Palladium(II)-catalyzed 1,3-dipolar cycloaddition of nitrones with enol ethers
  作者：Kazushige Hori、Junji Ito、Tetsuo Ohta、Isao Furukawa

  DOI：10.1016/s0040-4020(98)00776-5

  日期：1998.10

  The 1,3-dipolar cycloadditions of enol ethers as electron-rich olefins with C-phenyl-N-alkyl nitrones proceeded smoothly in the presence of easy handling palladium(II) catalysts under mild conditions to give isoxazolidines in good yield.

  在易处理的钯（II）催化剂的存在下，在温和的条件下，烯醇醚作为富电子烯烃的1,3-偶极环加成反应与C-苯基-N-烷基硝酮平稳进行，从而以高收率得到异恶唑烷。
• Reactions at high pressures. [3+2] Dipolar cycloaddition of nitrones with vinyl ethers
  作者：Carl Michael Dicken、Philip DeShong

  DOI：10.1021/jo00132a014

  日期：1982.5
• Determination of configuration and conformation of isoxazolidines by nuclear Overhauser effect difference spectroscopy
  作者：Philip DeShong、C. Michael Dicken、Ronald R. Staib、Alan J. Freyer、Steven M. Weinreb

  DOI：10.1021/jo00144a002

  日期：1982.11