(2'S,3'R,5S,6R)-3-[3-(p-chlorophenyl)-3-hydroxy-2-(p-methoxyphenoxy)propionyl]-3,4,5,6-tetrahydro-4-isopropyl-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one

• 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: (2'S,3'R,5S,6R)-3-[3-(p-chlorophenyl)-3-hydroxy-2-(p-methoxyphenoxy)propionyl]-3,4,5,6-tetrahydro-4-isopropyl-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one
• 英文别名: (5S,6R)-3-[(2S,3R)-3-(4-chlorophenyl)-3-hydroxy-2-(4-methoxyphenoxy)propanoyl]-5-methyl-6-phenyl-4-propan-2-yl-1,3,4-oxadiazinan-2-one
• 化学式: C₂₉H₃₁ClN₂O₆
• 分子量: 539.028
• InChiKey: AASZLYTYPGPCAM-VIIGGRGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对甲氧基苯氧乙酸 在 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 6.5h， 生成 (2'S,3'R,5S,6R)-3-[3-(p-chlorophenyl)-3-hydroxy-2-(p-methoxyphenoxy)propionyl]-3,4,5,6-tetrahydro-4-isopropyl-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one
  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.