| 1170354-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1170354-12-7
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: PMSSPBBHIUKJAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以8 g的产率得到
  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