(4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate | 1262206-05-2

• 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: (4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate
• 英文别名: ethyl (E,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-methyl-8-phenylmethoxyoct-2-enoate
• CAS: 1262206-05-2
• 化学式: C₂₄H₄₀O₄Si
• 分子量: 420.665
• InChiKey: FTTDYTXORKOOSR-QDAJVUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate 在 20 % Pd(OH)2/C 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 亚硝基苯 、 D-脯氨酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 1.34h， 生成 ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Palladium Hydroxide Catalyzed Isomerization of Primary Allylic Alcohols to Aldehydes: Application to the Formal Synthesis of (−)-Brevisamide

  摘要：

  The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.

  DOI：

  10.1021/ol102658d
• 作为产物：
  描述：

  4-苯基甲氧基-丁醛 在 2,6-二甲基吡啶 、 四氯化钛 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 1.75h， 生成 (4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate
  参考文献：
  名称：

  Palladium Hydroxide Catalyzed Isomerization of Primary Allylic Alcohols to Aldehydes: Application to the Formal Synthesis of (−)-Brevisamide

  摘要：

  The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.

  DOI：

  10.1021/ol102658d

文献信息

• Palladium Hydroxide Catalyzed Isomerization of Primary Allylic Alcohols to Aldehydes: Application to the Formal Synthesis of (−)-Brevisamide
  作者：Gowravaram Sabitha、Sambit Nayak、M. Bhikshapathi、J. S. Yadav

  DOI：10.1021/ol102658d

  日期：2011.2.4

  The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.