(βR,5R)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-β-phenyl-2-isoxazolidineethanol | 951214-74-7

• 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: (βR,5R)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-β-phenyl-2-isoxazolidineethanol
• 英文别名: (2R)-2-[(5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1,2-oxazolidin-2-yl]-2-phenylethanol
• CAS: 951214-74-7
• 化学式: C₁₈H₃₁NO₃Si
• 分子量: 337.535
• InChiKey: JGZNKPJHMXPPLH-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (βR,5R)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-β-phenyl-2-isoxazolidineethanol 在 盐酸 作用下， 以 甲醇 为溶剂， 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 以 甲苯 为溶剂， 反应 16.0h， 生成 (βR,5R)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-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

文献信息

• The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones
  作者：Shaikh A. Ali、Muhammad Z.N. Iman

  DOI：10.1016/j.tet.2007.06.067

  日期：2007.9

  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.