(15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine | 87302-60-1

• 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: (15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine
• 英文别名: (+)-(15S)-hydroxycryptopleurine；(14aS,15S)-2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizin-15-ol
• CAS: 87302-60-1
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: KKXLHPYVIGADHN-GBXCKJPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 10.0h， 生成 小穗苎麻素 、 cryptopleurine
  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：

  (14aS,15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>-11-quinolizidinone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以36%的产率得到(15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine
  参考文献：
  名称：

  Amino acids as chiral educts for asymmetric products. Chirally specific syntheses of tylophorine and cryptopleurine

  摘要：

  DOI：

  10.1021/jo00171a014

文献信息

• Total Synthesis of Phenanthro-Quinolizidine Alkaloids: (±)-Cryptopleurine, (±)-Boehmeriasin A, (±)-Boehmeriasin B and (±)-Hydroxycryptopleurine
  作者：Mingbo Cui、Qingmin Wang

  DOI：10.1002/ejoc.200900834

  日期：2009.11

  The first synthesis of (±)-boehmeriasin A and B and a concise synthesis of (±)-cryptopleurine and (±)-hydroxycryptopleurine are described. The piperidine ring of these alkaloids was constructed by the coupling of the phenanthrene ring with 2-bromopyridine through a nucleophilic substitution reaction and subsequent reduction of the resulting pyridyl ketone. The first crystal structure of a phenanthro-quinolizidine

  描述了 (±)-boehmeriasin A 和 B 的首次合成以及 (±)-cryptopleurine 和 (±)-hydroxycryptopleurine 的简明合成。这些生物碱的哌啶环是通过菲环与 2-溴吡啶通过亲核取代反应和随后得到的吡啶基酮的还原反应而构建的。还报道了菲-喹唑啉生物碱的第一个晶体结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Amino acids as chiral educts for asymmetric products. Chirally specific syntheses of tylophorine and cryptopleurine
  作者：Thomas F. Buckley、Rapoport Henry

  DOI：10.1021/jo00171a014

  日期：1983.11
• 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.