(5S,6R)-3,4,5,6,-tetrahydro-4-isopropyl-[2-(p-methoxyphenoxy)acetyl]-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one | 815620-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5S,6R)-3,4,5,6,-tetrahydro-4-isopropyl-[2-(p-methoxyphenoxy)acetyl]-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one
• 英文别名: (5S,6R)-3-[2-(4-methoxyphenoxy)acetyl]-5-methyl-6-phenyl-4-propan-2-yl-1,3,4-oxadiazinan-2-one
• CAS: 815620-25-8
• 化学式: C₂₂H₂₆N₂O₅
• 分子量: 398.459
• InChiKey: FOTJUQUWEMITSI-KKSFZXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S,6R)-3,4,5,6,-tetrahydro-4-isopropyl-[2-(p-methoxyphenoxy)acetyl]-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 在 sodium hydroxide 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (2S,3R)-methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionate
  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 草酰氯 、 lithium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (5S,6R)-3,4,5,6,-tetrahydro-4-isopropyl-[2-(p-methoxyphenoxy)acetyl]-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.