(2R,3S)-2,3-dihydroxy-3-phenylpropionamide | 206447-84-9

• 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,3S)-2,3-dihydroxy-3-phenylpropionamide
• 英文别名: (2R,3S)-2,3-dihydroxy-3-phenylpropanamide
• CAS: 206447-84-9
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: DNTDCDJASYYSJT-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-dihydroxy-3-phenylpropionamide 在 原乙酸三甲酯 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2-imino-(3S,4S)-3-acetoxy-4-phenyloxetane
  参考文献：
  名称：

  A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

  摘要：

  A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00049-4
• 作为产物：
  描述：

  甲基 (2R,3S)-(+)-2,3-二羟基-3-苯基丙酸盐 在 氨 作用下， 以99%的产率得到(2R,3S)-2,3-dihydroxy-3-phenylpropionamide
  参考文献：
  名称：

  A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

  摘要：

  A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00049-4

文献信息

• Diastereoselective β-Hydroxyalkylation and β-Hydroxycarboxylation of Amides­ by a Diels-Alder Strategy
  作者：Léon Ghosez、Deogratias Ntirampebura

  DOI：10.1055/s-2002-34367

  日期：——

  Acid chlorides readily condensed with N-silylated imines in the presence of a base to generate 2-azadienes. These underwent Diels-Alder cycloadditions with a wide variety of aldehydes.. In most cases the cycloadditions were diastereoselective in favor of the 3,4-cis-oxazinone adducts. Ethanolysis stereoselectively yielded products of hydroxyalkylation or hydroxycarboxylation of the primary amides derived

  在碱的存在下，酰氯很容易与 N-甲硅烷基化亚胺缩合生成 2-氮杂二烯。这些经历了与多种醛的 Diels-Alder 环加成反应。在大多数情况下，环加成反应是非对映选择性的，有利于 3,4-顺式-恶嗪酮加合物。乙醇解立体选择性地产生衍生自初始酰氯的伯酰胺的羟烷基化或羟羧化产物。