(-)-7-methoxycryptopleurine | 933982-92-4

• 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: (-)-7-methoxycryptopleurine
• 英文别名: (R)-7-methoxycryptopleurine；(14aR)-2,3,6,7-tetramethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
• CAS: 933982-92-4
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: LTUGUGXKMMPGRF-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-tert-butyl 2-((2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)-3,4-dihydropyridine-1-(2H)-carboxylate 在 盐酸 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 78.0h， 生成 (-)-7-methoxycryptopleurine
  参考文献：
  名称：

  Syntheses and Cytotoxicity of (R)- and (S)-7-Methoxycryptopleurine

  摘要：

  Two efficient protocols are described for the transformation of a key chiral homoallyllic sulfinamine intermediate in four steps into enantioenriched 7-methoxycryptopleurine. While one of the protocols relied on a rhodium catalyzed linear hydroformylation process, the alternative approach was based on a ring-closing metathesis from the corresponding N-allyl-sulfinamine. The cytotoxic evaluation of both enantiomers of the target compound demonstrated that the (R)-compound is much more potent than its antipode against the four cancer cell lines examined.

  DOI：

  10.1021/jo502660r

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.
• Syntheses and Cytotoxicity of (<i>R</i>)- and (<i>S</i>)-7-Methoxycryptopleurine
  作者：Cintia Anton-Torrecillas、Irene Bosque、Jose C. Gonzalez-Gomez、María Isabel Loza、José Brea

  DOI：10.1021/jo502660r

  日期：2015.1.16

  Two efficient protocols are described for the transformation of a key chiral homoallyllic sulfinamine intermediate in four steps into enantioenriched 7-methoxycryptopleurine. While one of the protocols relied on a rhodium catalyzed linear hydroformylation process, the alternative approach was based on a ring-closing metathesis from the corresponding N-allyl-sulfinamine. The cytotoxic evaluation of both enantiomers of the target compound demonstrated that the (R)-compound is much more potent than its antipode against the four cancer cell lines examined.