methyl (R)-N-benzoyl-4-methoxyphenylglycinate | 851136-38-4

• 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: methyl (R)-N-benzoyl-4-methoxyphenylglycinate
• 英文别名: methyl (2R)-2-benzamido-2-(4-methoxyphenyl)acetate
• CAS: 851136-38-4
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: KYRUHLFMZHUPBM-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-N-benzoyl-4-methoxyphenylglycinate 在 sodium tetrahydroborate 、 邻苯二甲酸二甲酯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.2h， 生成 (R)-N-(1-(4-methoxyphenyl)-2-oxoethyl)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：

  左旋对羟基苯甘氨酸甲酯 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (R)-N-benzoyl-4-methoxyphenylglycinate
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-radicamine B via anti,syn,syn-oxazine

  摘要：

  The stereoselective total synthesis of (+)-radicamine B was achieved using commercially available D-4-hydroxy-phenylglycine via chiral 1,3-oxazine, which has been applied to synthesis of amino polyols such as DAB-1, D-fagomine, and phytosphingosines. The key steps in this strategy were the palladium(0)-catalyzed stereoselective intramolecular oxazine formation, an extension of the chirality of anti,syn-oxazine with Lewis acid and vinylmagnesium bromide, and pyrrolidine ring formation via hydrogenation reaction. The chiral extension is also applicable to other chiral 1,3-oxazine derived from D-4-hydroxy-phenylglycine. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.01.009

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.
• Stereoselective total synthesis of (+)-radicamine B via anti,syn,syn-oxazine
  作者：Jin-Seok Kim、Gun-Woo Kim、Jong-Cheol Kang、In-Soo Myeong、Changyoung Jung、Yong-Taek Lee、Gyung-Ho Choo、Seok-Hwi Park、Gyu-Jin Lee、Won-Hun Ham

  DOI：10.1016/j.tetasy.2016.01.009

  日期：2016.3

  The stereoselective total synthesis of (+)-radicamine B was achieved using commercially available D-4-hydroxy-phenylglycine via chiral 1,3-oxazine, which has been applied to synthesis of amino polyols such as DAB-1, D-fagomine, and phytosphingosines. The key steps in this strategy were the palladium(0)-catalyzed stereoselective intramolecular oxazine formation, an extension of the chirality of anti,syn-oxazine with Lewis acid and vinylmagnesium bromide, and pyrrolidine ring formation via hydrogenation reaction. The chiral extension is also applicable to other chiral 1,3-oxazine derived from D-4-hydroxy-phenylglycine. (C) 2016 Elsevier Ltd. All rights reserved.