(+)-2-methyl-3-phenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (+)-2-methyl-3-phenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 2-methyl-3-phenyloxazinane-4,4-dicarboxylate
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: KKHVXOSKWXHRKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,1-环丙烷二甲酸二甲酯 、 N-methyl-α-phenylnitrone 在 4 A molecular sieve 、 chiral (S,S)-bisoxazoline derivative 、 nickel(II) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+)-2-methyl-3-phenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester 、 (+)-2-methyl-3-phenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective Addition of Nitrones to Activated Cyclopropanes

  摘要：

  In this paper, we demonstrate the first examples of chiral Lewis acid catalysis in the formation of tetrahydro-1,2-oxazines with very high enantioselectivity starting with diactivated cyclopropanes and nitrones (>90% yields and ee). Reactions with racemic substituted cyclopropanes provide approximately 1:1 diastereomeric tetrahydro-1,2-oxazine products with high enantioselectivity. Mechanistic information for the formation of the tetrahydro-1,2-oxazines is also detailed.

  DOI：

  10.1021/ja0421497

文献信息

• Enantioselective Addition of Nitrones to Activated Cyclopropanes
  作者：Mukund P. Sibi、Zhihua Ma、Craig P. Jasperse

  DOI：10.1021/ja0421497

  日期：2005.4.1

  In this paper, we demonstrate the first examples of chiral Lewis acid catalysis in the formation of tetrahydro-1,2-oxazines with very high enantioselectivity starting with diactivated cyclopropanes and nitrones (>90% yields and ee). Reactions with racemic substituted cyclopropanes provide approximately 1:1 diastereomeric tetrahydro-1,2-oxazine products with high enantioselectivity. Mechanistic information for the formation of the tetrahydro-1,2-oxazines is also detailed.