(2Z,4E,6Z,8E,10R,11R,12Z)-methyl-13-bromo-8,10-dimethyl-11-(triethylsilyloxy)tri-deca-2,4,6,8,12-pentaenoate | 1239951-21-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z,4E,6Z,8E,10R,11R,12Z)-methyl-13-bromo-8,10-dimethyl-11-(triethylsilyloxy)tri-deca-2,4,6,8,12-pentaenoate
• 英文别名: methyl (2Z,4E,6Z,8E,10R,11R,12Z)-13-bromo-8,10-dimethyl-11-triethylsilyloxytrideca-2,4,6,8,12-pentaenoate
• CAS: 1239951-21-3
• 化学式: C₂₂H₃₅BrO₃Si
• 分子量: 455.508
• InChiKey: KDENYXYOGXMBOZ-QZOWJCSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (2Z,4E)-5-(tributylstannyl)penta-2,4-dienoate 、 ((1Z,3R,4R,5E,7Z)-1-bromo-8-iodo-4,6-dimethylocta-1,5,7-trien-3-yloxy)triethylsilane 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 、 Tetrabutylammoniumsalz der Diphenylphosphinsaeure 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以85%的产率得到(2Z,4E,6Z,8E,10R,11R,12Z)-methyl-13-bromo-8,10-dimethyl-11-(triethylsilyloxy)tri-deca-2,4,6,8,12-pentaenoate
  参考文献：
  名称：

  Synthesis of the C1−C13 Tetraenoate Subunit of the Chivosazoles

  摘要：

  Using a combination of asymmetric vinylogous Mukaiyama aldol and Stifle cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.

  DOI：

  10.1021/ol101630p

文献信息

• Synthesis of the C1−C13 Tetraenoate Subunit of the Chivosazoles
  作者：Ian Paterson、S. B. Jennifer Kan、Lisa J. Gibson

  DOI：10.1021/ol101630p

  日期：2010.8.20

  Using a combination of asymmetric vinylogous Mukaiyama aldol and Stifle cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.