(2r,6s)-N-t-butoxycarbonyl-2-hydroxymethyl-6-methylpiperidine | 168610-12-6

• 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: (2r,6s)-N-t-butoxycarbonyl-2-hydroxymethyl-6-methylpiperidine
• 英文别名: tert-butyl (2R,6S)-2-(hydroxymethyl)-6-methylpiperidine-1-carboxylate
• CAS: 168610-12-6
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: QRQKEEFTQDHHHT-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 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：

  (2r,6s)-N-t-butoxycarbonyl-2-hydroxymethyl-6-methylpiperidine 在 chromium(VI) oxide 、 甲醇 、 disodium hydrogenphosphate 、 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 sodium amalgam 、 硫酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,3aR,4R,4aS,8aR,9aS)-decahydro-3-methyl-4-[2-(E)-[(2R,6S)-6-methylpiperidin-2-yl]ethenyl]naphtho[2,3-c]furan-1(3H)-one
  参考文献：
  名称：

  Total Syntheses of (+)-Himbacine and (+)-Himbeline

  摘要：

  DOI：

  10.1021/ja00141a036
• 作为产物：
  描述：

  (R)-2-哌啶甲醇 在 咪唑 、 sodium hydroxide 、 四甲基乙二胺 、 四丁基氟化铵 、 仲丁基锂 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (2r,6s)-N-t-butoxycarbonyl-2-hydroxymethyl-6-methylpiperidine
  参考文献：
  名称：

  Applications of Organosulfur Chemistry to Organic Synthesis:  Total Synthesis of (+)-Himbeline and (+)-Himbacine

  摘要：

  Total syntheses of(+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia-Lythgoe olefination. The preparation of sulfone 38 features an acid-promoted intramolecular Diels-Alder reaction of an alpha,beta-unsaturated thioester while the synthesis of 42 features a Beak, alkylation of piperidine 39.

  DOI：

  10.1021/jo970612a

文献信息

• Studies Directed Towards the Total Synthesis of (+)-Himbacine
  作者：Sven Hofman

  DOI：10.1055/s-1998-5928

  日期：1998.3

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.
• Total Syntheses of (+)-Himbacine and (+)-Himbeline
  作者：David J. Hart、Wen-Lian Wu、Alan P. Kozikowski

  DOI：10.1021/ja00141a036

  日期：1995.9
• Applications of Organosulfur Chemistry to Organic Synthesis:  Total Synthesis of (+)-Himbeline and (+)-Himbacine
  作者：David J. Hart、Jing Li、Wen-Lian Wu、Alan P. Kozikowski

  DOI：10.1021/jo970612a

  日期：1997.7.1

  Total syntheses of(+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia-Lythgoe olefination. The preparation of sulfone 38 features an acid-promoted intramolecular Diels-Alder reaction of an alpha,beta-unsaturated thioester while the synthesis of 42 features a Beak, alkylation of piperidine 39.