3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionic acid | 815620-35-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionic acid
• CAS: 815620-35-0
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: SUKKHPPFUYYMGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionic acid 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (2S,3R)-(-)-2,3-二羟基-3-苯基丙酸甲酯
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones

  摘要：

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.015
• 作为产物：
  描述：

  对甲氧基苯氧乙酸 在 sodium hydroxide 、 草酰氯 、 四氯化钛 、 lithium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionic acid
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones

  摘要：

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.015

文献信息

• Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones
  作者：Jeremy F. Vaughn、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2004.09.015

  日期：2004.11

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.