(2S,6S)-2-Methyl-6-[(E)-2-((3S,3aR,4R,4aR,9aS)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester | 344335-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (2S,6S)-2-Methyl-6-[(E)-2-((3S,3aR,4R,4aR,9aS)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,6S)-2-[(E)-2-[(1S,3aS,8aR,9R,9aR)-1-methyl-3-oxo-3a,5,6,7,8,8a,9,9a-octahydro-1H-benzo[f][2]benzofuran-9-yl]ethenyl]-6-methylpiperidine-1-carboxylate
• CAS: 344335-61-1
• 化学式: C₂₆H₃₉NO₄
• 分子量: 429.6
• InChiKey: APDGYHLVRMVOOR-LEEZWLEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2-Methyl-6-[(E)-2-((3S,3aR,4R,4aR,9aS)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester 在 RaNi 氢气 作用下， 以 甲醇 为溶剂， 生成 N-tert-butoxycarbonyl-himandravine 、 (2S,6S)-2-Methyl-6-[(E)-2-((3S,3aR,4R,4aS,8aS,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total Synthesis of Himandravine

  摘要：

  [GRAPHICS]The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.

  DOI：

  10.1021/ol010038w
• 作为产物：
  描述：

  tert-butyl (2S,6S)-2-[(E,5S)-5-hydroxyhex-1-en-3-ynyl]-6-methylpiperidine-1-carboxylate 在 Lindlar's catalyst 喹啉 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 (2S,6S)-2-Methyl-6-[(E)-2-((3S,3aR,4R,4aR,9aS)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total Synthesis of Himandravine

  摘要：

  [GRAPHICS]The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.

  DOI：

  10.1021/ol010038w

文献信息

• Total Synthesis of Himandravine
  作者：Samuel Chackalamannil、Robert Davies、Andrew T. McPhail

  DOI：10.1021/ol010038w

  日期：2001.5.1

  [GRAPHICS]The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.