(R)-7-Allyl-1,4-dithia-8-aza-spiro[4.5]decane-8-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester | 186045-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (R)-7-Allyl-1,4-dithia-8-aza-spiro[4.5]decane-8-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-naphthalen-2-ylpropan-2-yl)cyclohexyl] (7R)-7-prop-2-enyl-1,4-dithia-8-azaspiro[4.5]decane-8-carboxylate
• CAS: 186045-73-8
• 化学式: C₃₁H₄₁NO₂S₂
• 分子量: 523.804
• InChiKey: VCPHKLSMUNFPPQ-ZTHQAGOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-7-Allyl-1,4-dithia-8-aza-spiro[4.5]decane-8-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 在 镍 lithium aluminium tetrahydride 、 氢气 作用下， 生成 (-)-N-methylconiine
  参考文献：
  名称：

  Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions

  摘要：

  Lewis acid-promoted conjugate addition reaction of an allylsilane to a series of the chiral 8-arylmenthol-derived N-acyl-2,3-dihydro-4-pyridones leads to the 2-allyl-4-piperidones with moderate to high levels of asymmetric induction, indicating restacking contribution to chirality control. This methodology was applied to the asymmetric synthesis of (-)-N-methylconiine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02129-6
• 作为产物：
  描述：

  4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 在 三氟化硼乙醚 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-7-Allyl-1,4-dithia-8-aza-spiro[4.5]decane-8-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester
  参考文献：
  名称：

  Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions

  摘要：

  Lewis acid-promoted conjugate addition reaction of an allylsilane to a series of the chiral 8-arylmenthol-derived N-acyl-2,3-dihydro-4-pyridones leads to the 2-allyl-4-piperidones with moderate to high levels of asymmetric induction, indicating restacking contribution to chirality control. This methodology was applied to the asymmetric synthesis of (-)-N-methylconiine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02129-6