(R)-1-[(10-bromo-2,3,6-trimethoxyphenanthren-9-yl)methyl]-N,N-diethylpiperidine-2-carboxamide | 1219808-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (R)-1-[(10-bromo-2,3,6-trimethoxyphenanthren-9-yl)methyl]-N,N-diethylpiperidine-2-carboxamide
• 英文别名: (2R)-1-[(10-bromo-2,3,6-trimethoxyphenanthren-9-yl)methyl]-N,N-diethylpiperidine-2-carboxamide
• CAS: 1219808-17-9
• 化学式: C₂₈H₃₅BrN₂O₄
• 分子量: 543.501
• InChiKey: OAYSJFKRZQXYJT-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-[(10-bromo-2,3,6-trimethoxyphenanthren-9-yl)methyl]-N,N-diethylpiperidine-2-carboxamide 在 正丁基锂 、 四甲基乙二胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 13.0h， 以86%的产率得到(14aR,15R)-2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizin-15-ol
  参考文献：
  名称：

  Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

  摘要：

  A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14S,15S), 2a-(14aR,15R), and 2b were synthesized for the first time. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.135
• 作为产物：
  描述：

  10-bromo-9-(bromomethyl)-2,3,6-trimethoxyphenanthrene 、 (R)-N,N-diethylpiperidine-2-carboxamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以94%的产率得到(R)-1-[(10-bromo-2,3,6-trimethoxyphenanthren-9-yl)methyl]-N,N-diethylpiperidine-2-carboxamide
  参考文献：
  名称：

  Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

  摘要：

  A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14S,15S), 2a-(14aR,15R), and 2b were synthesized for the first time. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.135

文献信息

• Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation
  作者：Ziwen Wang、Qingmin Wang

  DOI：10.1016/j.tetlet.2009.12.135

  日期：2010.3

  A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14S,15S), 2a-(14aR,15R), and 2b were synthesized for the first time. (C) 2010 Elsevier Ltd. All rights reserved.