(-)-(4S,6S)-6-hydroxymethyl-4-methylpiperidin-2-one | 678148-65-7

• 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-methylpiperidin-2-one
• 英文别名: (4S,6S)-6-hydroxymethyl-4-methylpiperidin-2-one；(4S,6S)-6-(hydroxymethyl)-4-methylpiperidin-2-one
• CAS: 678148-65-7
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: PDUGUUKFHQTADY-WDSKDSINSA-N

物化性质

• 沸点：
  336.1±15.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (-)-(4S,6S)-6-hydroxymethyl-4-methylpiperidin-2-one 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S)-4-甲基-6-氧代-2-哌啶羧酸
  参考文献：
  名称：

  Sulfoxide-mediated diastereoselective Michael additions. New enantioselective synthesis of C-4 substituted 2-pyroaminoadipic acids

  摘要：

  Diastereoselective reactions of suitably functionalized homochiral beta-iminosulfoxides with Michael accepters provide a new and efficient route for the asymmetric synthesis of C-4 substituted 2-pyroaminoadipates. Extension of the scope of the sulfoxide-mediated aza-enolate conjugate addition (Hua's reaction) has also been explored. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01047-3
• 作为产物：
  描述：

  (-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one 在 W-2 Raney Ni 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 (-)-(4S,6S)-6-hydroxymethyl-4-methylpiperidin-2-one
  参考文献：
  名称：

  Sulfoxide-mediated diastereoselective Michael additions. New enantioselective synthesis of C-4 substituted 2-pyroaminoadipic acids

  摘要：

  Diastereoselective reactions of suitably functionalized homochiral beta-iminosulfoxides with Michael accepters provide a new and efficient route for the asymmetric synthesis of C-4 substituted 2-pyroaminoadipates. Extension of the scope of the sulfoxide-mediated aza-enolate conjugate addition (Hua's reaction) has also been explored. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01047-3

文献信息

• Enantioselective synthesis of (+)-(2S,4S,6S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolate
  作者：Hassan Acherki、Carlos Alvarez-Ibarra、Susana Guzmán-Fernández、Marı́a L. Quiroga-Feijóo

  DOI：10.1016/j.tetasy.2003.11.035

  日期：2004.2

  The enantioselective synthesis of (+)-(2S,4S,6S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolamide 16 is described. The absolute configuration of stereocenters introduced in (+)-16 was assigned on the basis of 1H NMR data. The results extend the chirality transfer with complete control of stereoselectivity from the sulfinyl group to the 4-position and, hence, to the 6- and 2-positions of the piperidine

  描述了（+）-（2 S，4 S，6 S）-1-乙氧基羰基-6-羟甲基-4-甲基哌酰胺16的对映选择性合成。根据1 H NMR数据确定（+）- 16中引入的立体中心的绝对构型。结果通过不对称诱导完全控制了立体选择性，从亚硫酰基到哌啶环的4位，进而到6位和2位，扩展了手性转移。
• Diastereoselective synthesis of 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones. A new approach to methyl l-(2S,4S)-4-methyl-6-oxopipecolate
  作者：Hassan Acherki、Carlos Alvarez-Ibarra、Alfonso de Dios、Marta Gutiérrez、Marı́a L. Quiroga

  DOI：10.1016/s0957-4166(01)00553-5

  日期：2001.12

  The sulfoxide-mediated diastereoselective Michael reaction of homochiral alpha-sulfinylketimines 1a-d and beta-substituted ene esters 2a-d (Hua's reaction) was explored. Straight forward cyclization of the open-chain adducts take place under the reaction conditions to provide the 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 3 and 7-12, whose stereochemistry is formed in the prior step. Furthermore. the role of the metal ion of the aza-enolate reagents and the steric demands of the O-alkyl ester group have been examined. It seems that the anti-diastereoselectivity depends on metal chelation by the oxygen of the ester as well as the oxygen of the sulfinyl group and the nitrogen in the aza-enolate ((Z)-configuration). In addition, the synthesis of methyl L-(2S,4S)-4-methyl-6-oxopipecolate has been achieved from the suitably functionalized 2-sulfinylketimine 1a (five steps; overall yield: 53-65%). (C) 2002 Elsevier Science Ltd. All rights reserved.