(2S,6R)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester | 691857-83-7

• 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: (2S,6R)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,6R)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylate
• CAS: 691857-83-7
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: JPQGHZSNACEAOY-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2S,6R)-2-(2-oxoethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine

  摘要：

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2008.12.008
• 作为产物：
  描述：

  (2S,6R)-2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-6-methylpiperidine-1-carboxylic acid tert-butyl ester 在 氢氟酸 作用下， 反应 12.0h， 生成 (2S,6R)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists

  摘要：

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.101