dimethyl (R)-2-(2-(acryloyloxy)-1-phenylethyl)isoxazolidine-5,5-dicarboxylate | 951215-08-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (R)-2-(2-(acryloyloxy)-1-phenylethyl)isoxazolidine-5,5-dicarboxylate
• CAS: 951215-08-0
• 化学式: C₁₈H₂₁NO₇
• 分子量: 363.367
• InChiKey: FIKMTLBWYBSBNO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl (R)-2-(2-(acryloyloxy)-1-phenylethyl)isoxazolidine-5,5-dicarboxylate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 6.17h， 生成 (βR,5R)-5-(hydroxymethyl)-β-phenyl-2-isoxazolidineethanol
  参考文献：
  名称：

  The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

  摘要：

  A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.067
• 作为产物：
  描述：

  (R)-α-(hydroxymethyl)benzylhydroxylamine 在 吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 11.0h， 生成 dimethyl (R)-2-(2-(acryloyloxy)-1-phenylethyl)isoxazolidine-5,5-dicarboxylate
  参考文献：
  名称：

  The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

  摘要：

  A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.067