2-甲基-2-丙基2,6-二(羟基甲基)-1-哌啶羧酸酯 | 198422-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-甲基-2-丙基2,6-二(羟基甲基)-1-哌啶羧酸酯
• 英文名称: (2R,6S)-2,6-Bis-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-Butyl (2R,6S)-2,6-bis(hydroxymethyl)piperidine-1-carboxylate
• CAS: 198422-46-7
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: CHSGQXHSSGXPHK-AOOOYVTPSA-N

物化性质

• 沸点：
  369.5±7.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基2,6-二(羟基甲基)-1-哌啶羧酸酯 在 silica gel 作用下， 反应 0.25h， 以100%的产率得到(5S,8aR)-5-Hydroxymethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

  摘要：

  Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.117
• 作为产物：
  描述：

  cis-O1-tert-butyl O2,O6-dimethyl piperidine-1,2,6-tricarboxylate 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 以70%的产率得到2-甲基-2-丙基2,6-二(羟基甲基)-1-哌啶羧酸酯
  参考文献：
  名称：

  Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

  摘要：

  Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.117

文献信息

• Synthesis of inhibitors of glutamyl-tRNA synthetase
  作者：Michel Desjardins、Julie Desgagnés、Lucille Lacoste、Fu Yang、Marie-Pascale Morin、Jacques Lapointe、Robert Chênevert

  DOI：10.1016/s0960-894x(97)00434-4

  日期：1997.9

  Glutamic acid esters in which the alcohol moiety is ribose, prolinol or substituted piperidines are inhibitors of E. coli glutamyl-tRNA synthetase. (C) 1997 Elsevier Science Ltd.
• Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2
  作者：Ashish P. Vartak、A. Gabriela Deaciuc、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2010.04.117

  日期：2010.6

  Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition. (C) 2010 Elsevier Ltd. All rights reserved.