(±)-2-{4-(3-quinolinyl)phenyl}-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one | 1443293-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (±)-2-{4-(3-quinolinyl)phenyl}-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• 英文别名: 3-(4-Quinolin-3-ylphenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one；3-(4-quinolin-3-ylphenyl)-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• CAS: 1443293-84-2
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: GEAKBFJKNQORJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 在 双三苯基磷二氯化钯 、 4-甲基苯磺酸吡啶 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 (±)-2-{4-(3-quinolinyl)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

文献信息

• 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
  作者：Shinichiro Fuse、Kennichi Inaba、Motoki Takagi、Masahiro Tanaka、Takatsugu Hirokawa、Kohei Johmoto、Hidehiro Uekusa、Kazuo Shin-ya、Takashi Takahashi、Takayuki Doi

  DOI：10.1016/j.ejmech.2013.05.030

  日期：2013.8

  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.