3-((2'R,3'R,5'S)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one | 850374-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-((2'R,3'R,5'S)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one
• 英文别名: 4-hydroxy-3-[(2R,3R,5S)-3-methyl-5-(6-methyloctyl)oxan-2-yl]-5-phenyl-1H-pyridin-2-one
• CAS: 850374-60-6
• 化学式: C₂₆H₃₇NO₃
• 分子量: 411.585
• InChiKey: JWPKQZDEPUCTMF-XHYUGHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-methyl-octa-1,6-diene 、 6-methyl-octa-1,5-diene 、 2-chloro-5-[(2R,3R)-5-ethenyl-3-methyl-3,6-dihydro-2H-pyran-2-yl]-3-phenyl-4,6-bis(phenylmethoxy)pyridine 在 Grubbs catalyst first generation 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 45.0~50.0 ℃ 、500.01 kPa 条件下， 反应 48.0h， 以8 mg的产率得到3-((2'R,3'R,5'R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure

  摘要：

  Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.025

文献信息

• New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs
  作者：Nicolas Brondel、Brigitte Renoux、Jean-Pierre Gesson

  DOI：10.1016/j.tetlet.2006.10.102

  日期：2006.12

  An efficient method for the synthesis of antitumor TMC-69-6H and related analogs which have been demonstrated to be phosphatase (PTP1B, VHR, and PP1) inhibitors, is reported. This strategy involves two key steps: a diastereoselective aldol reaction and a one-pot tandem ring-closing and cross metathesis for the construction of the pyran moiety. (c) 2006 Elsevier Ltd. All rights reserved.