(3S,4R)-3-benzyloxy-4-hydroxy-1-isopropylpiperidine | 1426142-54-2

• 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: (3S,4R)-3-benzyloxy-4-hydroxy-1-isopropylpiperidine
• 英文别名: (3S,4R)-3-phenylmethoxy-1-propan-2-ylpiperidin-4-ol
• CAS: 1426142-54-2
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: JDZPMJMXTIBDNG-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (3S,4R)-3-benzyloxy-4-hydroxy-1-isopropylpiperidine 、 (1S)-(-)-莰烷酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Synthesis of piperidin-4-ones starting from 2-(2-bromo-1,1-dimethylethyl)azetidines and 2-(2-mesyloxyethyl)azetidines through a ring expansion–oxidation protocol

  摘要：

  cis-2-(2-Bromo-1,1-dimethylethyl)azetidines were transformed into novel 5,5-dimethylpiperidin-4-ones through a ring expansion oxidation protocol upon heating in DMSO in the presence of Ag2CO3 or AgBF4. In addition, several 5,5-nor-dimethyl analogues of the latter piperidin-4-ones were synthesized in a selective way through a similar ring expansion oxidation approach involving treatment of cis-2-(2-mesyloxyethyl)azetidines with K2CO3 in DMSO. Furthermore, both a diastereoselective and an enantioselective reduction of the carbonyl function in piperidin-4-ones were performed through a chemical and an enzymatic approach, respectively. Whereas the NaBH4-induced reduction proceeded with cis-diastereoselectivity, alcohol dehydrogenase-mediated reductions resulted in either an S- or R-enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.045
• 作为产物：
  描述：

  cis-3-benzyloxy-1-isopropyl-2-(2-mesyloxyethyl)azetidine 在 R-specific alcohol dehydrogenase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 potassium carbonate 作用下， 以 二甲基亚砜 、 异丙醇 为溶剂， 反应 36.0h， 生成 (3S,4R)-3-benzyloxy-4-hydroxy-1-isopropylpiperidine
  参考文献：
  名称：

  Synthesis of piperidin-4-ones starting from 2-(2-bromo-1,1-dimethylethyl)azetidines and 2-(2-mesyloxyethyl)azetidines through a ring expansion–oxidation protocol

  摘要：

  cis-2-(2-Bromo-1,1-dimethylethyl)azetidines were transformed into novel 5,5-dimethylpiperidin-4-ones through a ring expansion oxidation protocol upon heating in DMSO in the presence of Ag2CO3 or AgBF4. In addition, several 5,5-nor-dimethyl analogues of the latter piperidin-4-ones were synthesized in a selective way through a similar ring expansion oxidation approach involving treatment of cis-2-(2-mesyloxyethyl)azetidines with K2CO3 in DMSO. Furthermore, both a diastereoselective and an enantioselective reduction of the carbonyl function in piperidin-4-ones were performed through a chemical and an enzymatic approach, respectively. Whereas the NaBH4-induced reduction proceeded with cis-diastereoselectivity, alcohol dehydrogenase-mediated reductions resulted in either an S- or R-enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.045

文献信息

• Synthesis of piperidin-4-ones starting from 2-(2-bromo-1,1-dimethylethyl)azetidines and 2-(2-mesyloxyethyl)azetidines through a ring expansion–oxidation protocol
  作者：Karen Mollet、Matthias D'hooghe、Leen Broeckx、Barbara Danneels、Tom Desmet、Norbert De Kimpe

  DOI：10.1016/j.tet.2013.01.045

  日期：2013.3

  cis-2-(2-Bromo-1,1-dimethylethyl)azetidines were transformed into novel 5,5-dimethylpiperidin-4-ones through a ring expansion oxidation protocol upon heating in DMSO in the presence of Ag2CO3 or AgBF4. In addition, several 5,5-nor-dimethyl analogues of the latter piperidin-4-ones were synthesized in a selective way through a similar ring expansion oxidation approach involving treatment of cis-2-(2-mesyloxyethyl)azetidines with K2CO3 in DMSO. Furthermore, both a diastereoselective and an enantioselective reduction of the carbonyl function in piperidin-4-ones were performed through a chemical and an enzymatic approach, respectively. Whereas the NaBH4-induced reduction proceeded with cis-diastereoselectivity, alcohol dehydrogenase-mediated reductions resulted in either an S- or R-enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.