2-methoxy-1-(methoxymethoxy)-6,9-dihydro-5H-benzo[7]annulen-5-ol | 1352550-82-3

• 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)-6,9-dihydro-5H-benzo[7]annulen-5-ol
• 英文别名: 3-methoxy-4-(methoxymethoxy)-8,9-dihydro-5H-benzo[7]annulen-9-ol
• CAS: 1352550-82-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: BKOISGJSPPBRDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-(methoxymethoxy)-6,9-dihydro-5H-benzo[7]annulen-5-ol 在 盐酸 、 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 、 对甲苯磺酰肼 、 barium(II) hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 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) 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-methoxy-1-(methoxymethoxy)-6,9-dihydro-5H-benzo[7]annulen-5-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

文献信息

• New cytotoxic benzosuberene analogs. Synthesis, molecular modeling and biological evaluation
  作者：Zecheng Chen、Andreas Maderna、Sai Chetan K. Sukuru、Melissa Wagenaar、Christopher J. O’Donnell、My-Hanh Lam、Sylvia Musto、Frank Loganzo

  DOI：10.1016/j.bmcl.2013.10.039

  日期：2013.12

  In this Letter we describe the synthesis and biological evaluation of new benzosuberene analogs with structural modifications on the B-ring. The focus was initially to probe the chemical space around the B-ring C-8 position. This position was readily available for derivatization chemistry using our recently developed new synthesis for this compound class. Furthermore, we describe two new B-ring analogs, one containing a diene and the other a cyclic ether group. Both new analogs show excellent potencies in tumor cell proliferation assays. In addition, we describe molecular modeling studies that provide a binding rationale for reference compound 8 in the colchicine binding site using the known colchicine crystal structure. We also examine whether the cell based potency data obtained with selected new analogs are supported by modeling results. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.