(R)-3-hydroxylamino-2-phenylethanol | 1041448-72-9

• 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: (R)-3-hydroxylamino-2-phenylethanol
• 英文别名: N-[(1R)-2-hydroxy-1-phenylethyl]methanimine oxide
• CAS: 1041448-72-9
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: UBOMBBGAXIJKGJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxylamino-2-phenylethanol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 (1R,5S)-methyl 2-(2-hydroxy-1-phenylethyl)-5-isoxazolidinecarboxylate
  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：

  聚合甲醛 、 (R)-α-(hydroxymethyl)benzylhydroxylamine 以 甲苯 为溶剂， 反应 2.0h， 生成 (R)-3-hydroxylamino-2-phenylethanol
  参考文献：
  名称：

  The Regio-and Stereo-Chemistry of 1,3-Dipolar Cycloaddition of a Chiral Methylenenitrone to 1,2-Disubstituted Alkenes

  摘要：

  研究人员对一系列对称和不对称的 1,2-二取代烯与手性、内部 H 键的 N-(2-羟基-1-苯基)亚甲基腈酮的环加成反应的区域和立体选择性进行了研究。在加成反应中观察到的区域选择性可以用前沿轨道相互作用来解释。研究发现，在无水溴化镁存在下，烯丙基位置上具有羟甲基取代基的烯烃会发生区域和高度立体选择性的环加成反应。

  DOI：

  10.3184/030823408x287087

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.
• The Regio-and Stereo-Chemistry of 1,3-Dipolar Cycloaddition of a Chiral Methylenenitrone to 1,2-Disubstituted Alkenes
  作者：Shaikh A. Ali、Muhammad Z.N. Iman

  DOI：10.3184/030823408x287087

  日期：2008.1

  A study of regio- and stereo-selectivity in the cycloaddition reactions of a series of symmetrical and unsymmetrical 1,2-disubstituted alkenes to the chiral, internally H-bonded N-(2-hydroxy-1-phenyl)methylenenitrone, has been carried out. The regioselectivity observed in the addition reactions is explained in terms of frontier orbital interactions. The alkenes having a hydroxymethyl substituent at the allylic position are found to undergo regio- as well as highly stereo-selective cycloaddition reactions in the presence of anhydrous magnesium bromide.

  研究人员对一系列对称和不对称的 1,2-二取代烯与手性、内部 H 键的 N-(2-羟基-1-苯基)亚甲基腈酮的环加成反应的区域和立体选择性进行了研究。在加成反应中观察到的区域选择性可以用前沿轨道相互作用来解释。研究发现，在无水溴化镁存在下，烯丙基位置上具有羟甲基取代基的烯烃会发生区域和高度立体选择性的环加成反应。