5-acetoxy-2,3-diphenyl-isoxazolidine | 19744-05-9

• 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: 5-acetoxy-2,3-diphenyl-isoxazolidine
• 英文别名: (2,3-diphenyl-1,2-oxazolidin-5-yl) acetate
• CAS: 19744-05-9
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: NFCRCWGPKGNBJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-acetoxy-2,3-diphenyl-isoxazolidine 在 硫酸 作用下， 反应 1.0h， 以85%的产率得到C-styryl-N-phenyl nitrone
  参考文献：
  名称：

  Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines.

  摘要：

  High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.

  DOI：

  10.1016/s0040-4020(01)88315-0
• 作为产物：
  描述：

  C,N-diphenylnitrone 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 5-acetoxy-2,3-diphenyl-isoxazolidine
  参考文献：
  名称：

  通过5-羟基异恶唑烷对芳族醛进行有效的C 2同源化

  摘要：

  乙醛的烯醇锂（由在n -BuLi存在下已知的THF环还原反应生成）与许多芳基N-苯基硝酮的反应可在高浓度下获得2-苯基-3-芳基-5-羟基异恶唑烷（反式+顺式）产量。相反，用一些N-烷基硝酮（分别为甲基和叔丁基）观察到低转化率或根本没有反应。碱（或酸）诱导的5-羟基异恶唑烷的分解可以高产率获得肉桂醛。因此，5-羟基异恶唑烷的合成和分解的结合为芳族醛的C 2-同系化提供了一种新的有效途径。

  DOI：

  10.1016/s0040-4020(01)86449-8

文献信息

• Cum,G. et al., Gazzetta Chimica Italiana, 1968, vol. 98, p. 782 - 794
  作者：Cum,G. et al.

  DOI：——

  日期：——
• Mukherjee, Shubhasish; Raunak; Dhawan, Ashish, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2670 - 2682
  作者：Mukherjee, Shubhasish、Raunak、Dhawan, Ashish、Poonam、Prasad, Ashok K.、Olsen, Carl E.、Cholli, Ashok L.、Errington, William、Raj, Hanumantharao G.、Watterson, Arthur C.、Parmar, Virinder S.

  DOI：——

  日期：——
• Hydrophobic effect on 1,3-dipolar cycloaddition reactions
  作者：Pramod S. Pandey、Inder K. Pandey

  DOI：10.1016/s0040-4039(97)01679-1

  日期：1997.10

  Rate and selectivity of 1,3-dipolar cyloaddition reactions of C,N-diphenyl-nitrone are influenced by hydrophobic effect. (C) 1997 Elsevier Science Ltd.
• An efficient C2-homologation of aromatic aldehydes via 5-hydroxyisoxazolidines
  作者：L Di Nunno、A Scilimati

  DOI：10.1016/s0040-4020(01)86449-8

  日期：1991.1

  The reaction of lithium enolate of acetaldehyde (generated by the known cycloreversion of THF in the presence of n-BuLi) with a number of aryl N-phenylnitrones affords 2-phenyl-3-aryl-5-hydroxyisoxazolidines (trans + cis) in high yields. A low conversion or no reaction at all were instead observed with some N-alkylnitrones (methyl and t-butyl, respectively). Base (or acid) induced decomposition of

  乙醛的烯醇锂（由在n -BuLi存在下已知的THF环还原反应生成）与许多芳基N-苯基硝酮的反应可在高浓度下获得2-苯基-3-芳基-5-羟基异恶唑烷（反式+顺式）产量。相反，用一些N-烷基硝酮（分别为甲基和叔丁基）观察到低转化率或根本没有反应。碱（或酸）诱导的5-羟基异恶唑烷的分解可以高产率获得肉桂醛。因此，5-羟基异恶唑烷的合成和分解的结合为芳族醛的C 2-同系化提供了一种新的有效途径。
• Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines.
  作者：Ugo Chiacchio、Angelo Liguori、Giovanni Romeo、Giovanni Sindona、Nicola Uccella

  DOI：10.1016/s0040-4020(01)88315-0

  日期：1992.1

  High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.