(E)-ethyl 4-((tert-butyldiphenylsilyloxy)methyl)-2-ethylhex-2-enoate | 1394253-60-1

• 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: (E)-ethyl 4-((tert-butyldiphenylsilyloxy)methyl)-2-ethylhex-2-enoate
• 英文别名: ethyl (E)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-ethylhex-2-enoate
• CAS: 1394253-60-1
• 化学式: C₂₇H₃₈O₃Si
• 分子量: 438.682
• InChiKey: IOJBRXYUWSMTML-BSYVCWPDSA-N

物化性质

• 沸点：
  487.9±45.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-((tert-butyldiphenylsilyloxy)methyl)-2-ethylhex-2-enoate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 异丙基氯化镁 、 四氯化钛 、 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 6.25h， 生成 (4E,7E,9E,12E)-5,9,11-triethyl-3-(hydroxymethyl)-7-methyl-13-phenyltrideca-4,7,9,12-tetraen-6-one
  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-乙基-1,3-丙二醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 97.0h， 生成 (E)-ethyl 4-((tert-butyldiphenylsilyloxy)methyl)-2-ethylhex-2-enoate
  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

文献信息

• Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A
  作者：Atahualpa Pinto、Christopher N. Boddy

  DOI：10.1016/j.bmcl.2012.06.052

  日期：2012.8

  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.