(R)-4-benzyl-3-((4R,5R,E)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl)oxazolidin-2-one | 1239951-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-benzyl-3-((4R,5R,E)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl)oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2E,4R,5R)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl]-1,3-oxazolidin-2-one
• CAS: 1239951-14-4
• 化学式: C₁₉H₂₁Br₂NO₄
• 分子量: 487.188
• InChiKey: SQKJLURUMGYMQE-HENRUPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-((4R,5R,E)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl)oxazolidin-2-one 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(R)-4-benzyl-3-((4R,5R,E)-7,7-dibromo-2,4-dimethyl-5-((triethylsilyl)oxy)hepta-2,6-dienoyl)oxazolidin-2-one
  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
• 作为产物：
  描述：

  (R)-4-benzyl-3-((1E,3E)-1-(tert-butyldimethylsilyloxy)-2-methylpenta-1,3-dienyl)oxazolidin-2-one 、 3,3-dibromoacrylaldehyde 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-4-benzyl-3-((4R,5R,E)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl)oxazolidin-2-one 、 (R)-4-benzyl-3-((E)-7,7-dibromo-5-hydroxy-2,4-dimethylhepta-2,6-dienoyl)oxazolidin-2-one
  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.