(1R,6R)-1-(hydroxymethyl)-3-[(1S)-1-phenylethyl]-7-oxa-3-azabicyclo[4.1.0]heptan-2-one | 1381968-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧哌啶
• 英文名称: (1R,6R)-1-(hydroxymethyl)-3-[(1S)-1-phenylethyl]-7-oxa-3-azabicyclo[4.1.0]heptan-2-one
• CAS: 1381968-82-6
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: LBVADHIGECSPML-ZKYQVNSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,6R)-1-(hydroxymethyl)-3-[(1S)-1-phenylethyl]-7-oxa-3-azabicyclo[4.1.0]heptan-2-one 在 Oxone 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate dihydrate 、 乙二胺四乙酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 48.25h， 生成 (1R,5R,6R)-5-hydroxy-5-(hydroxymethyl)-3-((S)-1-phenylethyl)-7-oxa-3-azabicyclo[4.1.0]heptan-4-one
  参考文献：
  名称：

  The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis

  摘要：

  A facile and environmentally friendly synthesis of both enantiomers of a biologically important 1-N-iminosugar (azasugar) is presented. To this end, the use of a very cheap and non-toxic reagent, such as sodium chlorite, is featured in two key reactions. Additionally, a highly stereoselective epoxidation with dimethyloxirane (DMDO), and regioselective acid-catalyzed epoxide ring opening are also two environmentally friendly reactions that are employed in this synthesis. For all the above-mentioned, and also taking into account that protecting groups were not employed, we would like to present this synthetic route as an efficient approach for the development of environmental and sustainable syntheses of highly oxygenated biologically important compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.08.054
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 盐酸 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 22.75h， 生成 (1R,6R)-1-(hydroxymethyl)-3-[(1S)-1-phenylethyl]-7-oxa-3-azabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  使用亚氯酸钠制备2,3-环氧乙烷的直接化学方法

  摘要：

  据报道，一种直接的方法是使用亚氯酸钠通过串联的C–H氧化/双键环氧化从叔烯丙胺制备2，3-环氧酰胺。显然，反应过程包括两个步骤：（i）用亚氯酸钠将起始烯丙胺烯丙基氧化为相应的不饱和烯丙基酰胺，然后（ii）由次氯酸根离子将烯丙基酰胺环氧化为2,3-环氧酰胺，形成通过还原亚氯酸钠就地还原。反应条件容许存在游离羟基和典型的官能团，例如TBS，芳基，烷基，烯丙基，乙酰基和苄基；然而，当基质中存在活化的芳环（例如芝麻酚）时，必须使用清除剂。

  DOI：

  10.1021/jo300542d

文献信息

• Direct Chemical Method for Preparing 2,3-Epoxyamides Using Sodium Chlorite
  作者：Lilia Fuentes、Urbano Osorio、Leticia Quintero、Herbert Höpfl、Nixache Vázquez-Cabrera、Fernando Sartillo-Piscil

  DOI：10.1021/jo300542d

  日期：2012.7.6

  mediated by hypochlorite ion, which is formed in situ by reduction of sodium chlorite. The reaction conditions tolerate the presence of free hydroxyl groups and typical functional groups such as TBS, aryl, alkyl, allyl, acetyl, and benzyl groups; however, when an activated aromatic ring (e.g., sesamol) is present in the substrate, the use of a scavenger is necessary.

  据报道，一种直接的方法是使用亚氯酸钠通过串联的C–H氧化/双键环氧化从叔烯丙胺制备2，3-环氧酰胺。显然，反应过程包括两个步骤：（i）用亚氯酸钠将起始烯丙胺烯丙基氧化为相应的不饱和烯丙基酰胺，然后（ii）由次氯酸根离子将烯丙基酰胺环氧化为2,3-环氧酰胺，形成通过还原亚氯酸钠就地还原。反应条件容许存在游离羟基和典型的官能团，例如TBS，芳基，烷基，烯丙基，乙酰基和苄基；然而，当基质中存在活化的芳环（例如芝麻酚）时，必须使用清除剂。
• The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis
  作者：Carlos G. Gómez-Fosado、Leticia Quintero、Lilia Fuentes、Fernando Sartillo-Piscil

  DOI：10.1016/j.tetlet.2015.08.054

  日期：2015.10

  A facile and environmentally friendly synthesis of both enantiomers of a biologically important 1-N-iminosugar (azasugar) is presented. To this end, the use of a very cheap and non-toxic reagent, such as sodium chlorite, is featured in two key reactions. Additionally, a highly stereoselective epoxidation with dimethyloxirane (DMDO), and regioselective acid-catalyzed epoxide ring opening are also two environmentally friendly reactions that are employed in this synthesis. For all the above-mentioned, and also taking into account that protecting groups were not employed, we would like to present this synthetic route as an efficient approach for the development of environmental and sustainable syntheses of highly oxygenated biologically important compounds. (C) 2015 Elsevier Ltd. All rights reserved.