2-Phenyl-[1,3]dioxane-5,5-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide] | 853065-10-8

• 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: 2-Phenyl-[1,3]dioxane-5,5-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide]
• CAS: 853065-10-8
• 化学式: C₂₂H₃₄N₂O₆
• 分子量: 422.522
• InChiKey: AJMXWCQYTMTGSF-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  117.12
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-Phenyl-[1,3]dioxane-5,5-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide] 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(4S)-2-[2-phenyl-5-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]-1,3-dioxan-5-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes as solution phase and immobilised ligands for highly enantioselective cyclopropanations

  摘要：

  2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes 5, which can be easily prepared in three steps from diethyl bishydroxymethylmalonate, amino alcohol and an aromatic aldehyde, have been used for the copper catalysed asymmetric cyclopropanation of styrene with ethyl diazoacetate in up to 99% ee for the trans-cyclopropane. Grafting onto a bromo-Wang resin produced an immobilised ligand 9 which gave the trans-cyclopropane in 65% ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.026
• 作为产物：
  描述：

  双羟甲基丙二酸二乙酯 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 2-Phenyl-[1,3]dioxane-5,5-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide]
  参考文献：
  名称：

  2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes as solution phase and immobilised ligands for highly enantioselective cyclopropanations

  摘要：

  2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes 5, which can be easily prepared in three steps from diethyl bishydroxymethylmalonate, amino alcohol and an aromatic aldehyde, have been used for the copper catalysed asymmetric cyclopropanation of styrene with ethyl diazoacetate in up to 99% ee for the trans-cyclopropane. Grafting onto a bromo-Wang resin produced an immobilised ligand 9 which gave the trans-cyclopropane in 65% ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.026