(1S,7R,8aR,9aS,10aS)-1-Isopropyl-7,10,10-trimethyl-decahydro-9-oxa-4a-aza-anthracene | 301311-74-0

• 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: (1S,7R,8aR,9aS,10aS)-1-Isopropyl-7,10,10-trimethyl-decahydro-9-oxa-4a-aza-anthracene
• 英文别名: (3S,6R,8R,10S,11S)-2,2,6-trimethyl-11-propan-2-yl-9-oxa-1-azatricyclo[8.4.0.03,8]tetradecane
• CAS: 301311-74-0
• 化学式: C₁₈H₃₃NO
• 分子量: 279.466
• InChiKey: SHFBJGLCEWCVDU-JJTUDDRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,7R,8aR,9aS,10aS)-1-Isopropyl-7,10,10-trimethyl-decahydro-9-oxa-4a-aza-anthracene 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以93%的产率得到(1R,2S,5R)-2-[1-((S)-3-Isopropyl-piperidin-1-yl)-1-methyl-ethyl]-5-methyl-cyclohexanol
  参考文献：
  名称：

  Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

  摘要：

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00230-5
• 作为产物：
  描述：

  (-)-aminomenthol 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 10.0h， 生成 (1S,7R,8aR,9aS,10aS)-1-Isopropyl-7,10,10-trimethyl-decahydro-9-oxa-4a-aza-anthracene
  参考文献：
  名称：

  Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

  摘要：

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00230-5

文献信息

• Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines
  作者：Rafael Pedrosa、Celia Andrés、Juan P Duque-Soladana、Carlos D Rosón

  DOI：10.1016/s0957-4166(00)00230-5

  日期：2000.7

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.