(1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(benzylamino)ethanol | 1258071-24-7

• 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: (1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(benzylamino)ethanol
• CAS: 1258071-24-7
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: KYLJGLFPEXLYJF-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 、 苄胺 以 甲醇 为溶剂， 反应 16.0h， 以56%的产率得到(1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(benzylamino)ethanol
  参考文献：
  名称：

  New class of β-aminoalcohol ligands derived from isosorbide and isomannide: application in hydrogen transfer reduction of prochiral ketones

  摘要：

  Starting from isosorbide and isomannide, two by-products from the starch industry, a family of chiral functionalized beta-aminoalcohols presenting a THF ring has been synthesized as potential ligands for hydrogen transfer reduction of prochiral ketones. Under optimal conditions, more than 70% ee with an excellent conversion were obtained for the HTR of the acetophenone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.060
• 作为试剂：
  描述：

  间硝基苯乙酮 在 [RuCl2(benzene)]2 、 (1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(benzylamino)ethanol 、 potassium tert-butylate 作用下， 以 异丙醇 为溶剂， 反应 21.0h， 生成 (R)-1-(3-硝基苯基)乙醇 、 (S)-1-(3-硝基苯基)乙醇
  参考文献：
  名称：

  New class of β-aminoalcohol ligands derived from isosorbide and isomannide: application in hydrogen transfer reduction of prochiral ketones

  摘要：

  Starting from isosorbide and isomannide, two by-products from the starch industry, a family of chiral functionalized beta-aminoalcohols presenting a THF ring has been synthesized as potential ligands for hydrogen transfer reduction of prochiral ketones. Under optimal conditions, more than 70% ee with an excellent conversion were obtained for the HTR of the acetophenone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.060

文献信息

• New class of β-aminoalcohol ligands derived from isosorbide and isomannide: application in hydrogen transfer reduction of prochiral ketones
  作者：Tin Thanh Le、Stéphane Guillarme、Christine Saluzzo

  DOI：10.1016/j.tet.2010.09.060

  日期：2010.11

  Starting from isosorbide and isomannide, two by-products from the starch industry, a family of chiral functionalized beta-aminoalcohols presenting a THF ring has been synthesized as potential ligands for hydrogen transfer reduction of prochiral ketones. Under optimal conditions, more than 70% ee with an excellent conversion were obtained for the HTR of the acetophenone. (C) 2010 Elsevier Ltd. All rights reserved.