(S)-1-((4-bromo-2-methylpent-4-enyloxy)methyl)-4-methoxybenzene | 895532-64-6

• 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: (S)-1-((4-bromo-2-methylpent-4-enyloxy)methyl)-4-methoxybenzene
• 英文别名: (S)-1-(4-methoxybenzyloxy)-2-methyl-2-bromopent-4-ene；1-[[(2S)-4-bromo-2-methylpent-4-enoxy]methyl]-4-methoxybenzene
• CAS: 895532-64-6
• 化学式: C₁₄H₁₉BrO₂
• 分子量: 299.208
• InChiKey: UPGBDZWBRBTPJM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-((4-bromo-2-methylpent-4-enyloxy)methyl)-4-methoxybenzene 、 (3R,4S)-3-(tert-butyldimethylsilyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutanone 在 叔丁基锂 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.5h， 以80%的产率得到(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-methylpent-1-en-2-yl)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutanol
  参考文献：
  名称：

  In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction

  摘要：

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).

  DOI：

  10.1021/ol060827j
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 、 (2S)-4-bromo-2-methyl-4-penten-2-ol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 以87%的产率得到(S)-1-((4-bromo-2-methylpent-4-enyloxy)methyl)-4-methoxybenzene
  参考文献：
  名称：

  In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction

  摘要：

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).

  DOI：

  10.1021/ol060827j

文献信息

• Pestalotiopsin A. Side Chain Installation and Exhaustive Probing of Olefin Metathesis as a Possible Tool for Elaborating the Cyclononene Ring
  作者：Leo A. Paquette、Shuzhi Dong、Gregory D. Parker

  DOI：10.1021/jo070862j

  日期：2007.9.1

  terminal double bonds in anticipation of the fact that the (E)-cyclononene substructure could be realized by ring-closing metathesis. This central issue was evaluated with several diene substrates and catalysts, all to no avail. Cross-metathesis experiments involving 59 and 65 with the functionalized heptene 60 revealed a marked difference in the inability to engage interaction with the ruthenium catalyst

  描述了一种针对不对称合成的鼠疫视蛋白A的程序。该路线以右旋环丁醇37开始，该环丁醇与对映体定义的结构单元ent - 15和16结合在一起。这些单元分别通过立体控制的1,2-亲核加成和抗醛醇偶合结合。完成这些简单的反应后，由于预期可以通过闭环复分解实现（E）-环壬烯亚结构这一事实，因此在续集中引入了末端双键。用几种二烯底物和催化剂评估了这个中心问题，但都无济于事。跨复分解实验，涉及59个和具有官能化庚烯60的化合物65和65表明不能与钌催化剂进行相互作用的显着差异。这种尴尬无法避免。
• In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction
  作者：Shuzhi Dong、Gregory D. Parker、Takahiro Tei、Leo A. Paquette

  DOI：10.1021/ol060827j

  日期：2006.5.1

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).