(3R,5R)-4-methyl-3,5-diphenylmorpholin-2-ol | 891821-38-8

• 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: (3R,5R)-4-methyl-3,5-diphenylmorpholin-2-ol
• CAS: 891821-38-8
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: SJLWISKPELEXKX-RTKIROINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-4-methyl-3,5-diphenylmorpholin-2-ol 在 diaza(1,3)bicyclo[5.4.0]undecane 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (3S,5R)-4-methyl-3,5-diphenylmorpholin-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction

  摘要：

  The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.023
• 作为产物：
  描述：

  (R)-4-Methyl-5-phenyl-3-phenylsulfanyl-morpholin-2-ol 、 苯硼酸 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到(3R,5R)-4-methyl-3,5-diphenylmorpholin-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction

  摘要：

  The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.023

文献信息

• Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction
  作者：Fabienne Berrée、AbdelMajid Debache、Yohann Marsac、Béatrice Collet、Pascale Girard-Le Bleiz、Bertrand Carboni

  DOI：10.1016/j.tet.2006.02.023

  日期：2006.4

  The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride. (c) 2006 Elsevier Ltd. All rights reserved.