(-)-(2S,4R)-2-hydroxymethyl-4-phenyl-6-piperidinone | 445474-74-8

• 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: (-)-(2S,4R)-2-hydroxymethyl-4-phenyl-6-piperidinone
• 英文别名: (4R,6S)-6-(hydroxymethyl)-4-phenylpiperidin-2-one
• CAS: 445474-74-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: FYXFEZKPKKIZSS-MNOVXSKESA-N

物化性质

• 沸点：
  440.4±38.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(2S,4R)-2-hydroxymethyl-4-phenyl-6-piperidinone 在 dimethyl sulfide borane 、 PH₂P(Ph-4-NMe₂) 、 偶氮二甲酸二乙酯 作用下， 生成 (2S,4S)-2-[(4-fluorophenoxy)methyl]-4-phenylpiperidine
  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：

  1-O-tert-butyl 2-O-methyl (2S)-6-oxo-2,3-dihydropyridine-1,2-dicarboxylate 在 三甲基氯硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-(2S,4R)-2-hydroxymethyl-4-phenyl-6-piperidinone
  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

文献信息

• Enantiopure bicyclic piperidinones: stereocontrolled conjugate additions leading to substituted piperidinones
  作者：Andrew G. Brewster、Simon Broady、Mark Hughes、Mark G. Moloney、Gordon Woods

  DOI：10.1039/b404325a

  日期：——

  The conjugate additions of Reformatsky reagents, organocuprate reagents, and hydroxylamines to a [4.3.0]-bicyclic enelactam derived from 6-oxopipecolic acid have been investigated, and found to be efficient, proceeding with excellent exo-stereocontrol, with the exception of N-benzyl-O-benzylhydroxylamine, which gives predominantly the product of endo-addition. These adducts can be readily converted

  已经研究了将Reformatsky试剂，有机铜试剂和羟胺共轭添加到衍生自6-氧代哌酸的[4.3.0]-双环烯内酰胺中的方法，发现该方法有效，除N外，还可进行出色的外-立体控制。 -苄基-O-苄基羟胺，主要给出内加产物。这些加合物可以容易地转化为取代的哌啶酮。