2-methoxy-1-(methoxymethoxy)-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-7H-benzo[7]annulene | 1352550-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methoxy-1-(methoxymethoxy)-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-7H-benzo[7]annulene
• CAS: 1352550-84-5
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: GTVUAIIWIBCQNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-(methoxymethoxy)-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-7H-benzo[7]annulene 在 盐酸 作用下， 以 甲醇 为溶剂， 以85%的产率得到3-methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol
  参考文献：
  名称：

  Synthesis of 3-methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol, a potent antineoplastic benzosuberene derivative for anti-cancer chemotherapy

  摘要：

  Benzosuberene 8 is a tubulin polymerization inhibitor that possesses remarkable potency against a variety of cancer cell lines. Herein, an efficient synthetic route for 8 is described featuring a Claisen rearrangement/RCM sequence and a late stage Suzuki coupling as the key steps. By adopting this strategy 8 was synthesized in eight steps in 18% overall yield starting from known compound 18. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.145
• 作为产物：
  描述：

  苯(甲)醛,3-羟基-4-甲氧基-2-(2-丙烯基)- 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四(三苯基膦)钯 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 、 barium(II) hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-methoxy-1-(methoxymethoxy)-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-7H-benzo[7]annulene
  参考文献：
  名称：

  Synthesis of 3-methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol, a potent antineoplastic benzosuberene derivative for anti-cancer chemotherapy

  摘要：

  Benzosuberene 8 is a tubulin polymerization inhibitor that possesses remarkable potency against a variety of cancer cell lines. Herein, an efficient synthetic route for 8 is described featuring a Claisen rearrangement/RCM sequence and a late stage Suzuki coupling as the key steps. By adopting this strategy 8 was synthesized in eight steps in 18% overall yield starting from known compound 18. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.145

文献信息

• Synthesis of 3-methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol, a potent antineoplastic benzosuberene derivative for anti-cancer chemotherapy
  作者：Zecheng Chen、Christopher J. O’Donnell、Andreas Maderna

  DOI：10.1016/j.tetlet.2011.10.145

  日期：2012.1

  Benzosuberene 8 is a tubulin polymerization inhibitor that possesses remarkable potency against a variety of cancer cell lines. Herein, an efficient synthetic route for 8 is described featuring a Claisen rearrangement/RCM sequence and a late stage Suzuki coupling as the key steps. By adopting this strategy 8 was synthesized in eight steps in 18% overall yield starting from known compound 18. (C) 2011 Elsevier Ltd. All rights reserved.