(±)-2-(3-iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one | 1449419-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-2-(3-iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• 英文别名: 2-(3-Iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one；3-(3-iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• CAS: 1449419-62-8
• 化学式: C₁₄H₁₁IO₃
• 分子量: 354.144
• InChiKey: VAZDSGYVBJQBBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-2-(3-iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one 、 3-氟苯基硼酸 在 双三苯基磷二氯化钯 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (±)-2-{3-(3-fluorophenyl)phenyl}-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
  参考文献：
  名称：

  Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A

  摘要：

  The spirocycle is a key structure found in many bioactive compounds. From the cytotoxic and spirocyclic natural product, spiromamakone A (1) and its analogues, a more synthetically accessible spiroacetal template 4 was designed based on structural similarity analysis. A total of 50 compounds were rapidly synthesized in only one or two synthetic steps from the starting compound, and their cytotoxicity was evaluated. As a result, (+/-)-(2R*,5R*)-2-(4-iodophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one (7d-II) was discovered and found to be fifteen-fold more cytotoxic than 1. The easily accessible spiroacetal 7d-II appeared to act in a manner similar to the highly oxidized natural product, spiromamakone A (1). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.030
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 、 1-(3-iodophenyl)ethane-1,2-diol 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 (±)-2-(3-iodophenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
  参考文献：
  名称：

  Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A

  摘要：

  The spirocycle is a key structure found in many bioactive compounds. From the cytotoxic and spirocyclic natural product, spiromamakone A (1) and its analogues, a more synthetically accessible spiroacetal template 4 was designed based on structural similarity analysis. A total of 50 compounds were rapidly synthesized in only one or two synthetic steps from the starting compound, and their cytotoxicity was evaluated. As a result, (+/-)-(2R*,5R*)-2-(4-iodophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one (7d-II) was discovered and found to be fifteen-fold more cytotoxic than 1. The easily accessible spiroacetal 7d-II appeared to act in a manner similar to the highly oxidized natural product, spiromamakone A (1). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.030