(2R,4E)-methyl 2,4-dimethyl-hex-4-enoate

• 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: (2R,4E)-methyl 2,4-dimethyl-hex-4-enoate
• 英文别名: methyl (E,2R)-2,4-dimethylhex-4-enoate
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: LDTBJXDKMULASH-WVXIBAHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4E)-methyl 2,4-dimethyl-hex-4-enoate 在 2,6-二甲基吡啶 、 锂硼氢 、 草酰氯 、 三氟甲磺酸二丁硼 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 (2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A

  摘要：

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.012
• 作为产物：
  描述：

  2-溴-cis-2-丁烯 、 (R)-(3-methoxy-2-methyl-3-oxopropyl)zinc(II) bromide 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.17h， 以68%的产率得到(2R,4E)-methyl 2,4-dimethyl-hex-4-enoate
  参考文献：
  名称：

  Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A

  摘要：

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.012