2-(4-Iodo-5-oxocyclohex-3-en-1-yl)ethyl 4-methylbenzenesulfonate | 1170354-13-8

• 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-(4-Iodo-5-oxocyclohex-3-en-1-yl)ethyl 4-methylbenzenesulfonate
• CAS: 1170354-13-8
• 化学式: C₁₅H₁₇IO₄S
• 分子量: 420.268
• InChiKey: VYZOZZIPUVRWPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Iodo-5-oxocyclohex-3-en-1-yl)ethyl 4-methylbenzenesulfonate 、 tert-butyl (4aS,9aS)-3-(2-bromo-5-methoxyphenyl)-5-methoxy-4a-(3-methoxyphenyl)-9,9a-dihydro-2H-indeno[2,1-b]pyridine-1-carboxylate 在 正丁基锂 、 硼酸三甲酯 、 二(氰基苯)二氯化钯 、 三苯胂 、 silver(l) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.17h， 以77%的产率得到tert-butyl (4aS,9aS)-5-methoxy-3-[5-methoxy-2-[4-[2-(4-methylphenyl)sulfonyloxyethyl]-6-oxocyclohexen-1-yl]phenyl]-4a-(3-methoxyphenyl)-9,9a-dihydro-2H-indeno[2,1-b]pyridine-1-carboxylate
  参考文献：
  名称：

  Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer

  摘要：

  A total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of cyclohexenones that allows for point-to-planar chirality transfer. This strategy makes it possible to program the desired atropisomeric outcome from a simple chiral cyclohexenone. By synthesizing atrop-haouamine A, this work has firmly established that natural haouamine exists as a single, nonequilibrating atropisomer. Finally, biological investigations demonstrate that the bent aromatic ring of this natural product is critical for anticancer activity against PC3 cells.

  DOI：

  10.1021/ja903745s
• 作为产物：
  描述：

  、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以81%的产率得到2-(4-Iodo-5-oxocyclohex-3-en-1-yl)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer

  摘要：

  A total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of cyclohexenones that allows for point-to-planar chirality transfer. This strategy makes it possible to program the desired atropisomeric outcome from a simple chiral cyclohexenone. By synthesizing atrop-haouamine A, this work has firmly established that natural haouamine exists as a single, nonequilibrating atropisomer. Finally, biological investigations demonstrate that the bent aromatic ring of this natural product is critical for anticancer activity against PC3 cells.

  DOI：

  10.1021/ja903745s