(4S,6S)-6-Hydroxymethyl-4-p-tolyl-piperidin-2-one | 445474-72-6

• 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: (4S,6S)-6-Hydroxymethyl-4-p-tolyl-piperidin-2-one
• CAS: 445474-72-6
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: XHUGUEHTWBOUMX-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,6S)-6-Hydroxymethyl-4-p-tolyl-piperidin-2-one 在 三丁基膦 、 dimethyl sulfide borane 作用下， 生成
  参考文献：
  名称：

  Stereocontrolled synthesis of a prototype library of enantiopure 2,4-disubstituted 4-aryl-6-piperidinones and piperidines

  摘要：

  Addition of a set of aryl cuprates to N-Boc O-TBDPS 2-hydroxymethyl 3.4-unsaturated 6-piperidinones affords syn-adducts in preference to anti when mixed Grignard-cuprates are used. Aryllithio cuprates give more of the anti-isomer in some cases. A library of 2-hydroxymethyl carbamates (27 compounds) and 2-hydroxymethyl aryl ethers and thioethers (19 compounds) was generated from a selection of 4-aryl-6-piperidinones, and some were further reduced to the corresponding piperidines (9 compounds). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00184-3
• 作为产物：
  描述：

  (4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-p-tolyl-piperidin-2-one 在 四丁基氟化铵 作用下， 生成 (4S,6S)-6-Hydroxymethyl-4-p-tolyl-piperidin-2-one
  参考文献：
  名称：

  Stereocontrolled synthesis of a prototype library of enantiopure 2,4-disubstituted 4-aryl-6-piperidinones and piperidines

  摘要：

  Addition of a set of aryl cuprates to N-Boc O-TBDPS 2-hydroxymethyl 3.4-unsaturated 6-piperidinones affords syn-adducts in preference to anti when mixed Grignard-cuprates are used. Aryllithio cuprates give more of the anti-isomer in some cases. A library of 2-hydroxymethyl carbamates (27 compounds) and 2-hydroxymethyl aryl ethers and thioethers (19 compounds) was generated from a selection of 4-aryl-6-piperidinones, and some were further reduced to the corresponding piperidines (9 compounds). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00184-3