(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-N-benzoylaminopropionitrile | 851136-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-N-benzoylaminopropionitrile
• 英文别名: N-[(1R,2R)-2-cyano-2-hydroxy-1-(4-methoxyphenyl)ethyl]benzamide
• CAS: 851136-40-8
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: ZLPSUYPCNBBJRO-JKSUJKDBSA-N

物化性质

• 沸点：
  613.9±55.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-N-benzoylaminopropionitrile 在 sodium tetrahydroborate 作用下， 生成 (R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]benzamide
  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：

  methyl (R)-N-benzoyl-4-methoxyphenylglycinate 在 sodium tetrahydroborate 、 邻苯二甲酸二甲酯 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.45h， 生成 (2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-N-benzoylaminopropionitrile
  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.