(4R,5R)-2-phenyl-4-(4-methoxyphenyl)-1,3-oxazoline-5-carbonitrile | 851136-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R,5R)-2-phenyl-4-(4-methoxyphenyl)-1,3-oxazoline-5-carbonitrile
• 英文别名: (4R,5R)-4-(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole-5-carbonitrile
• CAS: 851136-42-0
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: ALKXDIILKBQCQP-JKSUJKDBSA-N

物化性质

• 熔点：
  115 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  490.6±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2-phenyl-4-(4-methoxyphenyl)-1,3-oxazoline-5-carbonitrile 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.67h， 生成 (4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylic acid
  参考文献：
  名称：

  Synthesis of (−)‐Cytoxazone and (+)‐epi‐Cytoxazone: The Chiral Pool Approach

  摘要：

  Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.

  DOI：

  10.1081/scc-200048953
• 作为产物：
  描述：

  (R)-N-(1-(4-methoxyphenyl)-2-oxoethyl)benzamide 在 azodicarboxylate 、 溶剂黄146 、 三苯基膦 、 对硝基苯甲酸 作用下， 以 甲醇 为溶剂， 反应 3.25h， 生成 (4R,5R)-2-phenyl-4-(4-methoxyphenyl)-1,3-oxazoline-5-carbonitrile
  参考文献：
  名称：

  Synthesis of (−)‐Cytoxazone and (+)‐epi‐Cytoxazone: The Chiral Pool Approach

  摘要：

  Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.

  DOI：

  10.1081/scc-200048953

文献信息

• Synthesis of (−)‐Cytoxazone and (+)‐<i>epi</i>‐Cytoxazone: The Chiral Pool Approach
  作者：Zorana Tokic‐Vujosevic、Goran Petrovic、Bojana Rakic、Radomir Matovic、Radomir N. Saicic

  DOI：10.1081/scc-200048953

  日期：2005.1.1

  Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.