(E)-4-((tert-butyldiphenylsilyloxy)methyl)-2-ethyl-N-methoxy-N-methylhex-2-enamide | 1394253-72-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-4-((tert-butyldiphenylsilyloxy)methyl)-2-ethyl-N-methoxy-N-methylhex-2-enamide
• CAS: 1394253-72-5
• 化学式: C₂₇H₃₉NO₃Si
• 分子量: 453.697
• InChiKey: CJLXAGNNOJNRIZ-BSYVCWPDSA-N

物化性质

• 沸点：
  497.1±55.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-4-((tert-butyldiphenylsilyloxy)methyl)-2-ethyl-N-methoxy-N-methylhex-2-enamide 在 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 四氯化钛 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.08h， 生成 (2E,6E,8E,11E)-2,4,8,10-tetraethyl-6-methyl-5-oxo-12-phenyldodeca-2,6,8,11-tetraenal
  参考文献：
  名称：

  Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A

  摘要：

  The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.052
• 作为产物：
  描述：

  2-(((tert-butyldiphenylsilyl)oxy)methyl)butanal 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 26.17h， 生成 (E)-4-((tert-butyldiphenylsilyloxy)methyl)-2-ethyl-N-methoxy-N-methylhex-2-enamide
  参考文献：
  名称：

  Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A

  摘要：

  The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.052