10-cyano-2,3,6-trimethoxyphenanthrene | 74272-62-1

• 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: 10-cyano-2,3,6-trimethoxyphenanthrene
• 英文别名: 3,6,7-Trimethoxyphenanthrene-9-carbonitrile
• CAS: 74272-62-1
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: PQSPPXWDEPHXKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-cyano-2,3,6-trimethoxyphenanthrene 在 二异丁基氢化铝 、 盐酸 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 以99%的产率得到2,3,6-三甲氧基菲-10-甲醛
  参考文献：
  名称：

  Pd(OAc)2-催化直接芳香羰基化合成菲[9,10-b]indolizidin-9-ones、Phenanthro[9,10-b]quinolizidin-9-one和相关苯内酰胺

  摘要：

  菲 [9,10-b] indolizidin-9-ones、菲 [9,10-b] quinolizidin-9-one 和相关苯并内酰胺是通过使用 Pd(OAc)2 催化的直接芳香羰基化通过苯内酰胺环形成合成的。这也构成了代表性的菲吲哚里西啶和-喹唑西啶生物碱 (±)-tylophorine、(±)-antofine 和 (±)-cryptopleurine 的正式合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801047
• 作为产物：
  描述：

  2-(3,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-enenitrile 在 碘 、 methyloxirane 作用下， 以 乙腈 为溶剂， 生成 10-cyano-2,3,6-trimethoxyphenanthrene
  参考文献：
  名称：

  Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities

  摘要：

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.008

文献信息

• Synthesis of Phenanthro[9,10-<i>b</i>]indolizidin-9-ones, Phenanthro[9,10-<i>b</i>]quinolizidin-9-one, and Related Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation
  作者：Satoshi Yamashita、Nobuhito Kurono、Hisanori Senboku、Masao Tokuda、Kazuhiko Orito

  DOI：10.1002/ejoc.200801047

  日期：2009.3

  10-b]indolizidin-9-ones, phenanthro[9,10-b]quinolizidin-9-one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc)2-catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  菲 [9,10-b] indolizidin-9-ones、菲 [9,10-b] quinolizidin-9-one 和相关苯并内酰胺是通过使用 Pd(OAc)2 催化的直接芳香羰基化通过苯内酰胺环形成合成的。这也构成了代表性的菲吲哚里西啶和-喹唑西啶生物碱 (±)-tylophorine、(±)-antofine 和 (±)-cryptopleurine 的正式合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
  作者：Takashi Ikeda、Takashi Yaegashi、Takeshi Matsuzaki、Syusuke Hashimoto、Seigo Sawada

  DOI：10.1016/j.bmcl.2010.11.008

  日期：2011.1

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.