(1'R,3R)-1-(2-hydroxy-1-phenylethyl)-3-(3-methoxyphenyl)piperidin-2-one | 1342814-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1'R,3R)-1-(2-hydroxy-1-phenylethyl)-3-(3-methoxyphenyl)piperidin-2-one
• 英文别名: (3R)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-(3-methoxyphenyl)piperidin-2-one
• CAS: 1342814-89-4
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: PERBZVZPXCRIQV-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R,3R)-1-(2-hydroxy-1-phenylethyl)-3-(3-methoxyphenyl)piperidin-2-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以100%的产率得到(2'R,3R)-2-[3-(3-methoxyphenyl)-piperidin-1-yl]-2-phenylethanol
  参考文献：
  名称：

  Diastereoselective arylation of enantiopure 3-bromopiperidin-2-one derived from (R)-(−)-2-phenylglycinol with organocuprate reagents

  摘要：

  The diastereoselective substitution of 3-bromolactam derived from (R)-(-)-2-phenylglycinol with a variety of arylcuprate reagents is presented. The stereochemical outcome of the substitution reaction is discussed. The method provides an efficient and straightforward route to enantiopure 3-arylpiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.124
• 作为产物：
  描述：

  (1'R,3S)-3-bromo-1-(2-hydroxy-1-phenylethyl)piperidin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 CuI*0.75DMS 作用下， 以 四氢呋喃 、 二甲基硫 为溶剂， 反应 24.25h， 以82%的产率得到(1'R,3R)-1-(2-hydroxy-1-phenylethyl)-3-(3-methoxyphenyl)piperidin-2-one
  参考文献：
  名称：

  Diastereoselective arylation of enantiopure 3-bromopiperidin-2-one derived from (R)-(−)-2-phenylglycinol with organocuprate reagents

  摘要：

  The diastereoselective substitution of 3-bromolactam derived from (R)-(-)-2-phenylglycinol with a variety of arylcuprate reagents is presented. The stereochemical outcome of the substitution reaction is discussed. The method provides an efficient and straightforward route to enantiopure 3-arylpiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.124

文献信息

• Diastereoselective arylation of enantiopure 3-bromopiperidin-2-one derived from (R)-(−)-2-phenylglycinol with organocuprate reagents
  作者：Oscar Romero、Alejandro Castro、Joel L. Terán、Dino Gnecco、María L. Orea、Ángel Mendoza、Marcos Flores、Luis F. Roa、Jorge R. Juárez

  DOI：10.1016/j.tetlet.2011.08.124

  日期：2011.11

  The diastereoselective substitution of 3-bromolactam derived from (R)-(-)-2-phenylglycinol with a variety of arylcuprate reagents is presented. The stereochemical outcome of the substitution reaction is discussed. The method provides an efficient and straightforward route to enantiopure 3-arylpiperidines. (C) 2011 Elsevier Ltd. All rights reserved.